pyrocatechol
  CDK     08241813042D

  8  8  0  0  0  0  0  0  0  0999 V2000
    1.9458   -1.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6513   -2.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6478   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6523   -0.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9526    0.7460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6472    0.7491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6470    2.2491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9463   -0.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0 
  2  3  1  0  0  0  0 
  3  4  2  0  0  0  0 
  4  5  1  0  0  0  0 
  4  6  1  0  0  0  0 
  6  7  1  0  0  0  0 
  6  8  2  0  0  0  0 
  1  8  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H

> <InChIKey>
YCIMNLLNPGFGHC-UHFFFAOYSA-N

> <Molecular_formula>
C6H6O2

> <Major_Isotope_Mass>
110.036779432

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: Lactone Hydrolysis (BTMR0259)
Enzyme(s): Unspecified bacterial lactonase
Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2
Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N

Biotransformation_3
Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR0263)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H14O5/c12-8(2-4-11(15)16)5-7-1-3-9(13)10(14)6-7/h1,3,6,8,12-14H,2,4-5H2,(H,15,16)
Precursor InChIKey: JDBYFCLHVYVXCX-UHFFFAOYSA-N

Biotransformation_4
Reaction Type: Beta-oxidation of carboxylic acid (BTMR0275)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C11H14O4/c12-9-6-5-8(7-10(9)13)3-1-2-4-11(14)15/h5-7,12-13H,1-4H2,(H,14,15)
Precursor InChIKey: KTDWBJGUMIZRHU-UHFFFAOYSA-N

Biotransformation_5
Reaction Type: Beta-oxidation of carboxylic acid (BTMR0275)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)
Precursor InChIKey: DZAUWHJDUNRCTF-UHFFFAOYSA-N

Biotransformation_6
Reaction Type: Decarboxylation of benzoic acid (BTMR0282)
Enzyme(s): Unspecified bacterial decarboxylase
Precursor InChI: InChI=1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11)
Precursor InChIKey: YQUVCSBJEUQKSH-UHFFFAOYSA-N



$$$$
phloroglucinol
  CDK     08241813042D

  9  9  0  0  0  0  0  0  0  0999 V2000
    1.3000    0.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.5002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3000    0.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3000    2.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5989    3.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000    2.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5989    3.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0 
  2  3  1  0  0  0  0 
  2  4  1  0  0  0  0 
  4  5  2  0  0  0  0 
  5  6  1  0  0  0  0 
  5  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  1  8  1  0  0  0  0 
  8  9  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H

> <InChIKey>
QCDYQQDYXPDABM-UHFFFAOYSA-N

> <Molecular_formula>
C6H6O3

> <Major_Isotope_Mass>
126.03169405199999

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N



$$$$
3-phenylpropionic acid
  CDK     08241813042D

 11 11  0  0  0  0  0  0  0  0999 V2000
   -4.8712    2.0071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2731    2.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5721    2.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9740    2.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3250    2.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6245    2.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9236    2.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9231    0.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6236   -0.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    0.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5721    4.2571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0 
  4  5  1  0  0  0  0 
  5  6  2  0  0  0  0 
  6  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  8  9  1  0  0  0  0 
  9 10  2  0  0  0  0 
  5 10  1  0  0  0  0 
  1  3  1  0  0  0  0 
  3 11  2  0  0  0  0 
  3  2  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C9H10O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11)

> <InChIKey>
XMIIGOLPHOKFCH-UHFFFAOYSA-N

> <Molecular_formula>
C9H10O2

> <Major_Isotope_Mass>
150.06807956

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: 3p-Deydroxylation of substitued benzene (BTMR1314)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2
Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N

Biotransformation_3
Reaction Type: 4p-Deydroxylation of substitued benzene (BTMR1314)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-8(2-4-9)7-10-5-6-11(13)14-10/h1-4,10,12H,5-7H2
Precursor InChIKey: OXASBXALVLRTKO-UHFFFAOYSA-N

Biotransformation_4
Reaction Type: Lactone Hydrolysis (BTMR0259)
Enzyme(s): Unspecified bacterial lactonase
Precursor InChI: InChI=1S/C11H12O2/c12-11-7-6-10(13-11)8-9-4-2-1-3-5-9/h1-5,10H,6-8H2
Precursor InChIKey: OJKCYERWEGKEIS-UHFFFAOYSA-N

Biotransformation_5
Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR1314)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H14O3/c12-10(6-7-11(13)14)8-9-4-2-1-3-5-9/h1-5,10,12H,6-8H2,(H,13,14)
Precursor InChIKey: OTIPOAGPXXBSSB-UHFFFAOYSA-N

Biotransformation_6
Reaction Type: Beta-oxidation of carboxylic acid (BTMR0275)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C11H14O2/c12-11(13)9-5-4-8-10-6-2-1-3-7-10/h1-3,6-7H,4-5,8-9H2,(H,12,13)
Precursor InChIKey: BYHDDXPKOZIZRV-UHFFFAOYSA-N



$$$$
3,4-DIHYDROXYBENZOIC ACID
  CDK     08241813042D

 11 11  0  0  0  0  0  0  0  0999 V2000
    2.3080    3.9199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3080    2.4199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0090    1.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2905    2.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5895    1.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5891    0.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8881   -0.5801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2895   -0.5809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2898   -2.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0095    0.1691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6071    1.6699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0  0  0  0 
  4  5  1  0  0  0  0 
  5  6  2  0  0  0  0 
  6  7  1  0  0  0  0 
  6  8  1  0  0  0  0 
  8  9  1  0  0  0  0 
  8 10  2  0  0  0  0 
  3 10  1  0  0  0  0 
  1  2  1  0  0  0  0 
  2 11  2  0  0  0  0 
  2  3  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11)

> <InChIKey>
YQUVCSBJEUQKSH-UHFFFAOYSA-N

> <Molecular_formula>
C7H6O4

> <Major_Isotope_Mass>
154.026608672

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: Lactone Hydrolysis (BTMR0259)
Enzyme(s): Unspecified bacterial lactonase
Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2
Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N

Biotransformation_3
Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR0263)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H14O5/c12-8(2-4-11(15)16)5-7-1-3-9(13)10(14)6-7/h1,3,6,8,12-14H,2,4-5H2,(H,15,16)
Precursor InChIKey: JDBYFCLHVYVXCX-UHFFFAOYSA-N

Biotransformation_4
Reaction Type: Beta-oxidation of carboxylic acid (BTMR0275)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C11H14O4/c12-9-6-5-8(7-10(9)13)3-1-2-4-11(14)15/h5-7,12-13H,1-4H2,(H,14,15)
Precursor InChIKey: KTDWBJGUMIZRHU-UHFFFAOYSA-N

Biotransformation_5
Reaction Type: Beta-oxidation of carboxylic acid (BTMR0275)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)
Precursor InChIKey: DZAUWHJDUNRCTF-UHFFFAOYSA-N



$$$$
3-(4-Hydroxyphenyl)propionic acid
  CDK     08241813042D

 12 12  0  0  0  0  0  0  0  0999 V2000
   -1.3249   -1.5107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0148    0.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3175   -0.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0074    2.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2953    2.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2953    4.4765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5653    5.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9153    4.4765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2081    5.2372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9153    2.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5653    2.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6128    0.7457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0 
  4  5  1  0  0  0  0 
  5  6  2  0  0  0  0 
  6  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  8  9  1  0  0  0  0 
  8 10  1  0  0  0  0 
 10 11  2  0  0  0  0 
  5 11  1  0  0  0  0 
  1  3  1  0  0  0  0 
  3 12  2  0  0  0  0 
  3  2  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C9H10O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-2,4-5,10H,3,6H2,(H,11,12)

> <InChIKey>
NMHMNPHRMNGLLB-UHFFFAOYSA-N

> <Molecular_formula>
C9H10O3

> <Major_Isotope_Mass>
166.06299417999998

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: 3p-Deydroxylation of substitued benzene (BTMR1314)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2
Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N

Biotransformation_3
Reaction Type: Lactone Hydrolysis (BTMR0259)
Enzyme(s): Unspecified bacterial lactonase
Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-8(2-4-9)7-10-5-6-11(13)14-10/h1-4,10,12H,5-7H2
Precursor InChIKey: OXASBXALVLRTKO-UHFFFAOYSA-N

Biotransformation_4
Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR1314)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H14O4/c12-9-3-1-8(2-4-9)7-10(13)5-6-11(14)15/h1-4,10,12-13H,5-7H2,(H,14,15)
Precursor InChIKey: JCHZTLFRWGBCDD-UHFFFAOYSA-N

Biotransformation_5
Reaction Type: Beta-oxidation of carboxylic acid (BTMR0275)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C11H14O3/c12-10-7-5-9(6-8-10)3-1-2-4-11(13)14/h5-8,12H,1-4H2,(H,13,14)
Precursor InChIKey: YSSJQFONKASLKM-UHFFFAOYSA-N



$$$$
3-(3-hydroxyphenyl)propanoic acid
  CDK     08241813042D

 12 12  0  0  0  0  0  0  0  0999 V2000
    6.1679   -1.6943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5698   -1.6939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8690   -0.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2709   -0.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9717   -1.6934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9713   -3.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3233   -3.9365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6223   -3.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6268   -1.6943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9271   -0.9465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3273   -0.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8692    0.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0 
  4  5  1  0  0  0  0 
  5  6  2  0  0  0  0 
  6  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  8  9  1  0  0  0  0 
  9 10  1  0  0  0  0 
  9 11  2  0  0  0  0 
  5 11  1  0  0  0  0 
  1  3  1  0  0  0  0 
  3 12  2  0  0  0  0 
  3  2  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C9H10O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-3,6,10H,4-5H2,(H,11,12)

> <InChIKey>
QVWAEZJXDYOKEH-UHFFFAOYSA-N

> <Molecular_formula>
C9H10O3

> <Major_Isotope_Mass>
166.06299417999998

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: 4p-Deydroxylation of substitued benzene (BTMR1012)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2
Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N

Biotransformation_3
Reaction Type: Lactone Hydrolysis (BTMR0259)
Enzyme(s): Unspecified bacterial lactonase
Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-2-8(6-9)7-10-4-5-11(13)14-10/h1-3,6,10,12H,4-5,7H2
Precursor InChIKey: VYWFHBSBNKNWSB-UHFFFAOYSA-N

Biotransformation_4
Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR1012)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H14O4/c12-9-3-1-2-8(6-9)7-10(13)4-5-11(14)15/h1-3,6,10,12-13H,4-5,7H2,(H,14,15)
Precursor InChIKey: CBCIWEQMPVKOHC-UHFFFAOYSA-N

Biotransformation_5
Reaction Type: Beta-oxidation of carboxylic acid (BTMR0275)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C11H14O3/c12-10-6-3-5-9(8-10)4-1-2-7-11(13)14/h3,5-6,8,12H,1-2,4,7H2,(H,13,14)
Precursor InChIKey: CMLIEOOXQFWANJ-UHFFFAOYSA-N



$$$$
Vanillic acid
  CDK     08241813042D

 12 12  0  0  0  0  0  0  0  0999 V2000
    4.2566    0.5448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9576   -0.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6586    0.5448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6590    2.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3600    2.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9395    2.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2386    2.7948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9400    0.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2392   -0.2058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3590   -0.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9576   -1.7052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5381    0.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0  0  0  0 
  4  5  1  0  0  0  0 
  5  6  2  0  0  0  0 
  6  7  1  0  0  0  0 
  6  8  1  0  0  0  0 
  8  9  1  0  0  0  0 
  8 10  2  0  0  0  0 
  3 10  1  0  0  0  0 
  1  2  1  0  0  0  0 
  2 11  2  0  0  0  0 
  2  3  1  0  0  0  0 
  9 12  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)

> <InChIKey>
WKOLLVMJNQIZCI-UHFFFAOYSA-N

> <Molecular_formula>
C8H8O4

> <Major_Isotope_Mass>
168.042258736

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: Lactone Hydrolysis (BTMR0259)
Enzyme(s): Unspecified bacterial lactonase
Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2
Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N

Biotransformation_3
Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR0263)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H14O5/c12-8(2-4-11(15)16)5-7-1-3-9(13)10(14)6-7/h1,3,6,8,12-14H,2,4-5H2,(H,15,16)
Precursor InChIKey: JDBYFCLHVYVXCX-UHFFFAOYSA-N

Biotransformation_4
Reaction Type: Beta-oxidation of carboxylic acid (BTMR0275)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C11H14O4/c12-9-6-5-8(7-10(9)13)3-1-2-4-11(14)15/h5-7,12-13H,1-4H2,(H,14,15)
Precursor InChIKey: KTDWBJGUMIZRHU-UHFFFAOYSA-N

Biotransformation_5
Reaction Type: Beta-oxidation of carboxylic acid (BTMR0275)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)
Precursor InChIKey: DZAUWHJDUNRCTF-UHFFFAOYSA-N

Biotransformation_6
Reaction Type: Catechol O-methylation (BTMR0212)
Enzyme(s): EC 2.1.1.6
Precursor InChI: InChI=1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11)
Precursor InChIKey: YQUVCSBJEUQKSH-UHFFFAOYSA-N



$$$$
5-Phenylvaleric acid
  CDK     08241813042D

 13 13  0  0  0  0  0  0  0  0999 V2000
   -6.8197    3.1321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6236    3.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5207    3.8821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3245    3.8821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9745    3.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2740    3.8829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5731    3.1329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5726    1.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2731    0.8813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9740    1.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5207    5.3821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2216    3.1321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9226    3.8821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0 
  4  5  1  0  0  0  0 
  5  6  2  0  0  0  0 
  6  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  8  9  1  0  0  0  0 
  9 10  2  0  0  0  0 
  5 10  1  0  0  0  0 
  1  3  1  0  0  0  0 
  3 11  2  0  0  0  0 
  3 12  1  0  0  0  0 
 12 13  1  0  0  0  0 
  2 13  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C11H14O2/c12-11(13)9-5-4-8-10-6-2-1-3-7-10/h1-3,6-7H,4-5,8-9H2,(H,12,13)

> <InChIKey>
BYHDDXPKOZIZRV-UHFFFAOYSA-N

> <Molecular_formula>
C11H14O2

> <Major_Isotope_Mass>
178.099379688

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: 3p-Deydroxylation of substitued benzene (BTMR1314)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2
Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N

Biotransformation_3
Reaction Type: 4p-Deydroxylation of substitued benzene (BTMR1314)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-8(2-4-9)7-10-5-6-11(13)14-10/h1-4,10,12H,5-7H2
Precursor InChIKey: OXASBXALVLRTKO-UHFFFAOYSA-N

Biotransformation_4
Reaction Type: Lactone Hydrolysis (BTMR0259)
Enzyme(s): Unspecified bacterial lactonase
Precursor InChI: InChI=1S/C11H12O2/c12-11-7-6-10(13-11)8-9-4-2-1-3-5-9/h1-5,10H,6-8H2
Precursor InChIKey: OJKCYERWEGKEIS-UHFFFAOYSA-N

Biotransformation_5
Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR0263)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H14O3/c12-10(6-7-11(13)14)8-9-4-2-1-3-5-9/h1-5,10,12H,6-8H2,(H,13,14)
Precursor InChIKey: OTIPOAGPXXBSSB-UHFFFAOYSA-N



$$$$
Hippuric acid
  CDK     08241813042D

 13 13  0  0  0  0  0  0  0  0999 V2000
   -5.8454    3.6946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6493    3.6946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6498    2.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9493    3.6954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2483    2.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2478    1.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9483    0.6938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6493    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6493    5.1946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5464    2.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5464    1.4446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2474    3.6946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9483    2.9446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0  0  0  0 
  4  5  1  0  0  0  0 
  5  6  2  0  0  0  0 
  6  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  3  8  1  0  0  0  0 
  2  9  2  0  0  0  0 
  2  3  1  0  0  0  0 
  1 10  1  0  0  0  0 
 10 11  2  0  0  0  0 
 10 12  1  0  0  0  0 
 12 13  1  0  0  0  0 
 13  2  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12)

> <InChIKey>
QIAFMBKCNZACKA-UHFFFAOYSA-N

> <Molecular_formula>
C9H9NO3

> <Major_Isotope_Mass>
179.058243148

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: 3p-Deydroxylation of substitued benzene (BTMR1314)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2
Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N

Biotransformation_3
Reaction Type: 4p-Deydroxylation of substitued benzene (BTMR1314)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-8(2-4-9)7-10-5-6-11(13)14-10/h1-4,10,12H,5-7H2
Precursor InChIKey: OXASBXALVLRTKO-UHFFFAOYSA-N

Biotransformation_4
Reaction Type: Lactone Hydrolysis (BTMR0259)
Enzyme(s): Unspecified bacterial lactonase
Precursor InChI: InChI=1S/C11H12O2/c12-11-7-6-10(13-11)8-9-4-2-1-3-5-9/h1-5,10H,6-8H2
Precursor InChIKey: OJKCYERWEGKEIS-UHFFFAOYSA-N

Biotransformation_5
Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR1314)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H14O3/c12-10(6-7-11(13)14)8-9-4-2-1-3-5-9/h1-5,10,12H,6-8H2,(H,13,14)
Precursor InChIKey: OTIPOAGPXXBSSB-UHFFFAOYSA-N

Biotransformation_6
Reaction Type: Beta-oxidation of carboxylic acid (BTMR1314)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C11H14O2/c12-11(13)9-5-4-8-10-6-2-1-3-7-10/h1-3,6-7H,4-5,8-9H2,(H,12,13)
Precursor InChIKey: BYHDDXPKOZIZRV-UHFFFAOYSA-N

Biotransformation_7
Reaction Type: Beta-oxidation of carboxylic acid (BTMR1314)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C9H10O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11)
Precursor InChIKey: XMIIGOLPHOKFCH-UHFFFAOYSA-N

Biotransformation_8
Reaction Type: Glycination of aromatic acid (BTMR0206)
Enzyme(s): EC 2.3.1.13
Precursor InChI: InChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)
Precursor InChIKey: WPYMKLBDIGXBTP-UHFFFAOYSA-N



$$$$
Dihydrocaffeic acid
  CDK     08241813042D

 13 13  0  0  0  0  0  0  0  0999 V2000
    4.9068    1.6704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3087    1.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6077    0.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0097    0.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2894    1.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2889    3.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5879    3.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8874    3.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1865    3.9204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8879    1.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1871    0.9197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5889    0.9195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6077   -0.5796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0 
  4  5  1  0  0  0  0 
  5  6  2  0  0  0  0 
  6  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  8  9  1  0  0  0  0 
  8 10  1  0  0  0  0 
 10 11  1  0  0  0  0 
 10 12  2  0  0  0  0 
  5 12  1  0  0  0  0 
  1  3  1  0  0  0  0 
  3 13  2  0  0  0  0 
  3  2  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)

> <InChIKey>
DZAUWHJDUNRCTF-UHFFFAOYSA-N

> <Molecular_formula>
C9H10O4

> <Major_Isotope_Mass>
182.0579088

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: Lactone Hydrolysis (BTMR0259)
Enzyme(s): Unspecified bacterial lactonase
Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2
Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N

Biotransformation_3
Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR0263)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H14O5/c12-8(2-4-11(15)16)5-7-1-3-9(13)10(14)6-7/h1,3,6,8,12-14H,2,4-5H2,(H,15,16)
Precursor InChIKey: JDBYFCLHVYVXCX-UHFFFAOYSA-N

Biotransformation_4
Reaction Type: Beta-oxidation of carboxylic acid (BTMR0275)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C11H14O4/c12-9-6-5-8(7-10(9)13)3-1-2-4-11(14)15/h5-7,12-13H,1-4H2,(H,14,15)
Precursor InChIKey: KTDWBJGUMIZRHU-UHFFFAOYSA-N



$$$$
4-hydroxy-5-phenyl-valeric acid
  CDK     08241813042D

 14 14  0  0  0  0  0  0  0  0999 V2000
   -5.9865    5.8676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4865    3.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4865    5.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0135    3.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7635    1.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2644    1.9710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0144    0.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2635   -0.6276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7627   -0.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0127    0.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7365    7.1666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7365    4.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2365    4.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2365    1.9705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0 
  4  5  1  0  0  0  0 
  5  6  2  0  0  0  0 
  6  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  8  9  1  0  0  0  0 
  9 10  2  0  0  0  0 
  5 10  1  0  0  0  0 
  1  3  1  0  0  0  0 
  3 11  2  0  0  0  0 
  3 12  1  0  0  0  0 
 12 13  1  0  0  0  0 
  2 13  1  0  0  0  0 
 14  2  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C11H14O3/c12-10(6-7-11(13)14)8-9-4-2-1-3-5-9/h1-5,10,12H,6-8H2,(H,13,14)

> <InChIKey>
OTIPOAGPXXBSSB-UHFFFAOYSA-N

> <Molecular_formula>
C11H14O3

> <Major_Isotope_Mass>
194.094294308

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: 3p-Deydroxylation of substitued benzene (BTMR1314)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2
Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N

Biotransformation_3
Reaction Type: 4p-Deydroxylation of substitued benzene (BTMR1314)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-8(2-4-9)7-10-5-6-11(13)14-10/h1-4,10,12H,5-7H2
Precursor InChIKey: OXASBXALVLRTKO-UHFFFAOYSA-N

Biotransformation_4
Reaction Type: Lactone Hydrolysis (BTMR0259)
Enzyme(s): Unspecified bacterial lactonase
Precursor InChI: InChI=1S/C11H12O2/c12-11-7-6-10(13-11)8-9-4-2-1-3-5-9/h1-5,10H,6-8H2
Precursor InChIKey: OJKCYERWEGKEIS-UHFFFAOYSA-N



$$$$
5-(4-hydroxyphenyl)pentanoic Acid
  CDK     08241813042D

 14 14  0  0  0  0  0  0  0  0999 V2000
   -3.5795    3.5756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6166    3.5501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2768    4.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9193    4.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2147    3.5373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5137    4.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7982    3.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8237    2.0183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1289    1.2790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5247    1.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2001    2.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2694    5.8192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9814    3.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3213    4.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0 
  4  5  1  0  0  0  0 
  5  6  2  0  0  0  0 
  6  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  8  9  1  0  0  0  0 
  8 10  1  0  0  0  0 
 10 11  2  0  0  0  0 
  5 11  1  0  0  0  0 
  1  3  1  0  0  0  0 
  3 12  2  0  0  0  0 
  3 13  1  0  0  0  0 
 13 14  1  0  0  0  0 
  2 14  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C11H14O3/c12-10-7-5-9(6-8-10)3-1-2-4-11(13)14/h5-8,12H,1-4H2,(H,13,14)

> <InChIKey>
YSSJQFONKASLKM-UHFFFAOYSA-N

> <Molecular_formula>
C11H14O3

> <Major_Isotope_Mass>
194.09429430799997

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: 3p-Deydroxylation of substitued benzene (BTMR1314)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2
Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N

Biotransformation_3
Reaction Type: Lactone Hydrolysis (BTMR0259)
Enzyme(s): Unspecified bacterial lactonase
Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-8(2-4-9)7-10-5-6-11(13)14-10/h1-4,10,12H,5-7H2
Precursor InChIKey: OXASBXALVLRTKO-UHFFFAOYSA-N

Biotransformation_4
Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR0263)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H14O4/c12-9-3-1-8(2-4-9)7-10(13)5-6-11(14)15/h1-4,10,12-13H,5-7H2,(H,14,15)
Precursor InChIKey: JCHZTLFRWGBCDD-UHFFFAOYSA-N



$$$$
5-(3-hydroxyphenyl)pentanoic Acid
  CDK     08241813042D

 14 14  0  0  0  0  0  0  0  0999 V2000
   -3.5708   -2.0610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6253   -2.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2719   -2.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9242   -2.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2234   -2.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2239   -0.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5184    0.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8174   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8219   -2.0615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1222   -2.8093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5224   -2.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2722   -4.3112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9728   -2.0615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3261   -2.8117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0 
  4  5  1  0  0  0  0 
  5  6  2  0  0  0  0 
  6  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  8  9  1  0  0  0  0 
  9 10  1  0  0  0  0 
  9 11  2  0  0  0  0 
  5 11  1  0  0  0  0 
  1  3  1  0  0  0  0 
  3 12  2  0  0  0  0 
  3 13  1  0  0  0  0 
 13 14  1  0  0  0  0 
  2 14  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C11H14O3/c12-10-6-3-5-9(8-10)4-1-2-7-11(13)14/h3,5-6,8,12H,1-2,4,7H2,(H,13,14)

> <InChIKey>
CMLIEOOXQFWANJ-UHFFFAOYSA-N

> <Molecular_formula>
C11H14O3

> <Major_Isotope_Mass>
194.094294308

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: 4p-Deydroxylation of substitued benzene (BTMR1012)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2
Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N

Biotransformation_3
Reaction Type: Lactone Hydrolysis (BTMR0259)
Enzyme(s): Unspecified bacterial lactonase
Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-2-8(6-9)7-10-4-5-11(13)14-10/h1-3,6,10,12H,4-5,7H2
Precursor InChIKey: VYWFHBSBNKNWSB-UHFFFAOYSA-N

Biotransformation_4
Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR0263)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H14O4/c12-9-3-1-2-8(6-9)7-10(13)4-5-11(14)15/h1-3,6,10,12-13H,4-5,7H2,(H,14,15)
Precursor InChIKey: CBCIWEQMPVKOHC-UHFFFAOYSA-N



$$$$
5-[(3,4-dihydroxyphenyl)methyl]oxolan-2-one
  CDK     08241813042D

 15 16  0  0  0  0  0  0  0  0999 V2000
    4.3919   -3.8072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0929   -3.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5003   -2.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7242   -3.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5083   -2.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6616   -1.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5544   -0.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9236   -1.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1395   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0768   -2.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4456   -3.1426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8609   -3.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9667   -3.1230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8974   -1.4317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3959   -1.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0 
  2  4  1  0  0  0  0 
  4  5  1  0  0  0  0 
  5  6  2  0  0  0  0 
  6  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  8  9  1  0  0  0  0 
  8 10  1  0  0  0  0 
 10 11  1  0  0  0  0 
 10 12  2  0  0  0  0 
  5 12  1  0  0  0  0 
  1  3  1  0  0  0  0 
  3 13  2  0  0  0  0 
  3 14  1  0  0  0  0 
 14 15  1  0  0  0  0 
  2 15  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2

> <InChIKey>
ZNXXWTPQHVLMQT-UHFFFAOYSA-N

> <Molecular_formula>
C11H12O4

> <Major_Isotope_Mass>
208.073558864

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N



$$$$

  CDK     08241813042D

 18 18  0  0  0  0  0  0  0  0999 V2000
   -7.1445    3.6946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9483    3.6946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8454    4.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6493    4.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6498    3.6946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9493    4.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2483    3.6954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2478    2.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9483    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6493    2.1938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8454    5.9446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5464    3.6946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2474    4.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9483    2.1946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2474   -0.0554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2474    1.4446    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7604    2.8541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7246    1.1841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0 
  4  5  1  0  0  0  0 
  5  6  2  0  0  0  0 
  6  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  8  9  1  0  0  0  0 
  9 10  2  0  0  0  0 
  5 10  1  0  0  0  0 
  1  3  1  0  0  0  0 
  3 11  2  0  0  0  0 
  3 12  1  0  0  0  0 
 12 13  1  0  0  0  0 
  2 13  1  0  0  0  0 
 14  2  1  0  0  0  0 
 15 16  1  0  0  0  0 
 16 17  2  0  0  0  0 
 16 18  2  0  0  0  0 
 16 14  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C11H14O6S/c12-11(13)7-6-10(17-18(14,15)16)8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,12,13)(H,14,15,16)

> <InChIKey>
GAQUQQROGBFRNX-UHFFFAOYSA-N

> <Molecular_formula>
C11H14O6S

> <Major_Isotope_Mass>
274.051109168

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: 3p-Deydroxylation of substitued benzene (BTMR1314)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2
Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N

Biotransformation_3
Reaction Type: 4p-Deydroxylation of substitued benzene (BTMR1314)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-8(2-4-9)7-10-5-6-11(13)14-10/h1-4,10,12H,5-7H2
Precursor InChIKey: OXASBXALVLRTKO-UHFFFAOYSA-N

Biotransformation_4
Reaction Type: Lactone Hydrolysis (BTMR0259)
Enzyme(s): Unspecified bacterial lactonase
Precursor InChI: InChI=1S/C11H12O2/c12-11-7-6-10(13-11)8-9-4-2-1-3-5-9/h1-5,10H,6-8H2
Precursor InChIKey: OJKCYERWEGKEIS-UHFFFAOYSA-N

Biotransformation_5
Reaction Type: Sulfation of secondary alcohol (BTMR0502)
Enzyme(s): EC 2.8.2.2
Precursor InChI: InChI=1S/C11H14O3/c12-10(6-7-11(13)14)8-9-4-2-1-3-5-9/h1-5,10,12H,6-8H2,(H,13,14)
Precursor InChIKey: OTIPOAGPXXBSSB-UHFFFAOYSA-N



$$$$

  CDK     08241813042D

 18 18  0  0  0  0  0  0  0  0999 V2000
    8.4228    1.1137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2267    1.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1201    0.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9240    0.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6287    1.1520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6704    0.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9549    1.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9804    2.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2856    3.4103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6813    3.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6432    2.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1127   -1.1299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8247    1.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5220    0.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8836    3.3888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5784    2.6496    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5330    1.4926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6047    1.5085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0 
  4  5  1  0  0  0  0 
  5  6  2  0  0  0  0 
  6  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  8  9  1  0  0  0  0 
  8 10  1  0  0  0  0 
 10 11  2  0  0  0  0 
  5 11  1  0  0  0  0 
  1  3  1  0  0  0  0 
  3 12  2  0  0  0  0 
  3 13  1  0  0  0  0 
 13 14  1  0  0  0  0 
  2 14  1  0  0  0  0 
 15 16  1  0  0  0  0 
 16 17  2  0  0  0  0 
 16 18  2  0  0  0  0 
 16  9  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C11H14O6S/c12-11(13)4-2-1-3-9-5-7-10(8-6-9)17-18(14,15)16/h5-8H,1-4H2,(H,12,13)(H,14,15,16)

> <InChIKey>
MYPJIIMLOWTKLI-UHFFFAOYSA-N

> <Molecular_formula>
C11H14O6S

> <Major_Isotope_Mass>
274.051109168

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: 3p-Deydroxylation of substitued benzene (BTMR1314)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2
Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N

Biotransformation_3
Reaction Type: Lactone Hydrolysis (BTMR0259)
Enzyme(s): Unspecified bacterial lactonase
Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-8(2-4-9)7-10-5-6-11(13)14-10/h1-4,10,12H,5-7H2
Precursor InChIKey: OXASBXALVLRTKO-UHFFFAOYSA-N

Biotransformation_4
Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR1314)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H14O4/c12-9-3-1-8(2-4-9)7-10(13)5-6-11(14)15/h1-4,10,12-13H,5-7H2,(H,14,15)
Precursor InChIKey: JCHZTLFRWGBCDD-UHFFFAOYSA-N

Biotransformation_5
Reaction Type: 4-OH sulfonation of phenolic compound (BTMR0197)
Enzyme(s): EC 2.8.2.1
Precursor InChI: InChI=1S/C11H14O3/c12-10-7-5-9(6-8-10)3-1-2-4-11(13)14/h5-8,12H,1-4H2,(H,13,14)
Precursor InChIKey: YSSJQFONKASLKM-UHFFFAOYSA-N



$$$$

  CDK     08241813042D

 18 18  0  0  0  0  0  0  0  0999 V2000
   -5.6620   -1.0206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4659   -1.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3631   -1.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8331   -1.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1322   -1.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1327    0.4790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4272    1.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7262    0.4712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7308   -1.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0311   -1.7688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4312   -1.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3633   -3.2708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0639   -1.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7650   -1.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6291   -1.7644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3288   -1.0166    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.2911    0.1341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3627    0.1308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0 
  4  5  1  0  0  0  0 
  5  6  2  0  0  0  0 
  6  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  8  9  1  0  0  0  0 
  9 10  1  0  0  0  0 
  9 11  2  0  0  0  0 
  5 11  1  0  0  0  0 
  1  3  1  0  0  0  0 
  3 12  2  0  0  0  0 
  3 13  1  0  0  0  0 
 13 14  1  0  0  0  0 
  2 14  1  0  0  0  0 
 15 16  1  0  0  0  0 
 16 17  2  0  0  0  0 
 16 18  2  0  0  0  0 
 16 10  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C11H14O6S/c12-11(13)7-2-1-4-9-5-3-6-10(8-9)17-18(14,15)16/h3,5-6,8H,1-2,4,7H2,(H,12,13)(H,14,15,16)

> <InChIKey>
WZBQIUSHSKDLFF-UHFFFAOYSA-N

> <Molecular_formula>
C11H14O6S

> <Major_Isotope_Mass>
274.051109168

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: 4p-Deydroxylation of substitued benzene (BTMR1012)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2
Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N

Biotransformation_3
Reaction Type: Lactone Hydrolysis (BTMR0259)
Enzyme(s): Unspecified bacterial lactonase
Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-2-8(6-9)7-10-4-5-11(13)14-10/h1-3,6,10,12H,4-5,7H2
Precursor InChIKey: VYWFHBSBNKNWSB-UHFFFAOYSA-N

Biotransformation_4
Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR1012)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H14O4/c12-9-3-1-2-8(6-9)7-10(13)4-5-11(14)15/h1-3,6,10,12-13H,4-5,7H2,(H,14,15)
Precursor InChIKey: CBCIWEQMPVKOHC-UHFFFAOYSA-N

Biotransformation_5
Reaction Type: 3-OH sulfonation of phenolic compound (BTMR0196)
Enzyme(s): EC 2.8.2.1
Precursor InChI: InChI=1S/C11H14O3/c12-10-6-3-5-9(8-10)4-1-2-7-11(13)14/h3,5-6,8,12H,1-2,4,7H2,(H,13,14)
Precursor InChIKey: CMLIEOOXQFWANJ-UHFFFAOYSA-N



$$$$
4-[(2S)-2-Hydroxy-3-(2,4,6-trihydroxyphenyl)propyl]phenol
  CDK     08241813042D

 20 21  0  0  1  0  0  0  0  0999 V2000
    2.5995   -1.9650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5995   -3.4650    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3005   -4.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0014   -3.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2981   -4.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2979   -5.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5971   -3.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5967   -1.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8957   -1.2150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2971   -1.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0019   -1.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3011   -1.2143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8985   -4.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1976   -3.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1902   -1.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4565   -1.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8102   -1.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0992   -1.1850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8175   -3.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4712   -4.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0 
  2  3  1  0  0  0  0 
  3  4  1  0  0  0  0 
  4  5  2  0  0  0  0 
  5  6  1  0  0  0  0 
  5  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  8  9  1  0  0  0  0 
  8 10  1  0  0  0  0 
 10 11  2  0  0  0  0 
  4 11  1  0  0  0  0 
 11 12  1  0  0  0  0 
  2 13  1  0  0  0  0 
 13 14  1  0  0  0  0 
 14 15  2  0  0  0  0 
 15 16  1  0  0  0  0 
 16 17  2  0  0  0  0 
 17 18  1  0  0  0  0 
 17 19  1  0  0  0  0 
 19 20  2  0  0  0  0 
 14 20  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C15H16O5/c16-10-3-1-9(2-4-10)5-11(17)6-13-14(19)7-12(18)8-15(13)20/h1-4,7-8,11,16-20H,5-6H2/t11-/m0/s1

> <InChIKey>
QLKSONFIZUVQEN-NSHDSACASA-N

> <Molecular_formula>
C15H16O5

> <Major_Isotope_Mass>
276.099773612

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0257)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: 3p-Deydroxylation of substitued benzene (BTMR1314)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C15H16O6/c16-9(3-8-1-2-12(18)15(21)4-8)5-11-13(19)6-10(17)7-14(11)20/h1-2,4,6-7,9,16-21H,3,5H2/t9-/m0/s1
Precursor InChIKey: OFUFTNROAPAIQL-VIFPVBQESA-N



$$$$
1,3,5-Benzenetriol, 2-[(2S)-2-hydroxy-3-(3-hydroxyphenyl)propyl]-
  CDK     08241813042D

 20 21  0  0  1  0  0  0  0  0999 V2000
    0.9677   -4.3911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9677   -2.8911    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2667   -2.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5658   -2.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8653   -2.1403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8650   -0.6403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1643   -2.8903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1638   -4.3911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4629   -5.1411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8643   -5.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5653   -4.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2661   -5.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3314   -2.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6304   -2.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6306   -4.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9250   -5.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2242   -4.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2290   -2.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5294   -2.1447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9296   -2.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0 
  2  3  1  0  0  0  0 
  3  4  1  0  0  0  0 
  4  5  2  0  0  0  0 
  5  6  1  0  0  0  0 
  5  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  8  9  1  0  0  0  0 
  8 10  1  0  0  0  0 
 10 11  2  0  0  0  0 
  4 11  1  0  0  0  0 
 11 12  1  0  0  0  0 
  2 13  1  0  0  0  0 
 13 14  1  0  0  0  0 
 14 15  2  0  0  0  0 
 15 16  1  0  0  0  0 
 16 17  2  0  0  0  0 
 17 18  1  0  0  0  0 
 18 19  1  0  0  0  0 
 18 20  2  0  0  0  0 
 14 20  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C15H16O5/c16-10-3-1-2-9(4-10)5-11(17)6-13-14(19)7-12(18)8-15(13)20/h1-4,7-8,11,16-20H,5-6H2/t11-/m0/s1

> <InChIKey>
FCLPAEDZIOXNSO-NSHDSACASA-N

> <Molecular_formula>
C15H16O5

> <Major_Isotope_Mass>
276.099773612

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0257)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: 4p-Deydroxylation of substitued benzene (BTMR1012)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C15H16O6/c16-9(3-8-1-2-12(18)15(21)4-8)5-11-13(19)6-10(17)7-14(11)20/h1-2,4,6-7,9,16-21H,3,5H2/t9-/m0/s1
Precursor InChIKey: OFUFTNROAPAIQL-VIFPVBQESA-N



$$$$
SCHEMBL16711631
  CDK     08241813042D

 20 21  0  0  0  0  0  0  0  0999 V2000
   -0.0023   -1.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2944   -2.7300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5959   -1.9843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6053   -0.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9081    0.2514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3083    0.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3135    1.7630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0068   -0.4827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0170    2.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3030    1.7675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6030    2.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6030    4.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9040    4.7539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3030    4.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3079    6.2674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0170    4.0075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3156    4.7582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9019    1.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2011    2.5170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9017    0.2672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0 
  2  3  1  0  0  0  0 
  3  4  2  0  0  0  0 
  4  5  1  0  0  0  0 
  4  6  1  0  0  0  0 
  6  7  1  0  0  0  0 
  6  8  2  0  0  0  0 
  1  8  1  0  0  0  0 
  9  7  1  0  0  0  0 
  9 10  1  0  0  0  0 
 10 11  1  0  0  0  0 
 11 12  1  0  0  0  0 
 12 13  1  0  0  0  0 
 12 14  1  0  0  0  0 
 14 15  1  0  0  0  0 
 14 16  1  0  0  0  0 
  9 16  1  0  0  0  0 
 16 17  1  0  0  0  0 
 11 18  1  0  0  0  0 
 18 19  1  0  0  0  0 
 18 20  2  0  0  0  0 
M  END
> <InChI>
InChI=1S/C12H14O8/c13-5-3-1-2-4-6(5)19-12-9(16)7(14)8(15)10(20-12)11(17)18/h1-4,7-10,12-16H,(H,17,18)

> <InChIKey>
ICPYZFZFSLTYID-UHFFFAOYSA-N

> <Molecular_formula>
C12H14O8

> <Major_Isotope_Mass>
286.06886740799996

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: Lactone Hydrolysis (BTMR0259)
Enzyme(s): Unspecified bacterial lactonase
Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2
Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N

Biotransformation_3
Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR0263)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H14O5/c12-8(2-4-11(15)16)5-7-1-3-9(13)10(14)6-7/h1,3,6,8,12-14H,2,4-5H2,(H,15,16)
Precursor InChIKey: JDBYFCLHVYVXCX-UHFFFAOYSA-N

Biotransformation_4
Reaction Type: Beta-oxidation of carboxylic acid (BTMR0275)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C11H14O4/c12-9-6-5-8(7-10(9)13)3-1-2-4-11(14)15/h5-7,12-13H,1-4H2,(H,14,15)
Precursor InChIKey: KTDWBJGUMIZRHU-UHFFFAOYSA-N

Biotransformation_5
Reaction Type: Beta-oxidation of carboxylic acid (BTMR0275)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)
Precursor InChIKey: DZAUWHJDUNRCTF-UHFFFAOYSA-N

Biotransformation_6
Reaction Type: Decarboxylation of benzoic acid (BTMR0282)
Enzyme(s): Unspecified bacterial decarboxylase
Precursor InChI: InChI=1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11)
Precursor InChIKey: YQUVCSBJEUQKSH-UHFFFAOYSA-N

Biotransformation_7
Reaction Type: Aromatic -OH glucuronidation (BTMR0166)
Enzyme(s): EC 2.4.1.17
Precursor InChI: InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H
Precursor InChIKey: YCIMNLLNPGFGHC-UHFFFAOYSA-N



$$$$
CHEBI:134254
  CDK     08241813042D

 19 20  0  0  0  0  0  0  0  0999 V2000
    5.8882   -4.5579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5892   -3.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9966   -3.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2205   -4.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0046   -3.5435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1579   -2.0505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9419   -1.1721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4273   -1.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6432   -0.9084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5805   -3.2797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9493   -3.8934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6354   -4.1581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4630   -3.8737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3937   -2.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8922   -2.3432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5338   -3.6285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1651   -3.0148    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0887   -1.9701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0071   -1.7734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0 
  2  4  1  0  0  0  0 
  4  5  1  0  0  0  0 
  5  6  2  0  0  0  0 
  6  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  8  9  1  0  0  0  0 
  8 10  1  0  0  0  0 
 10 11  1  0  0  0  0 
 10 12  2  0  0  0  0 
  5 12  1  0  0  0  0 
  1  3  1  0  0  0  0 
  3 13  2  0  0  0  0 
  3 14  1  0  0  0  0 
 14 15  1  0  0  0  0 
  2 15  1  0  0  0  0 
 16 17  1  0  0  0  0 
 17 18  2  0  0  0  0 
 17 19  2  0  0  0  0 
 17 11  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C11H12O7S/c12-9-3-1-7(5-8-2-4-11(13)17-8)6-10(9)18-19(14,15)16/h1,3,6,8,12H,2,4-5H2,(H,14,15,16)

> <InChIKey>
YAXFVDUJDAQPTJ-UHFFFAOYSA-N

> <Molecular_formula>
C11H12O7S

> <Major_Isotope_Mass>
288.030373724

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: 3-OH sulfonation of phenolic compound (BTMR0196)
Enzyme(s): EC 2.8.2.1
Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2
Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N



$$$$
4-Hydroxy-5-(4'-hydroxyphenyl)-valeric acid-4'-O-sulphate
  CDK     08241813042D

 19 19  0  0  0  0  0  0  0  0999 V2000
   -5.7978    1.9512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6017    1.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4951    2.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7010    2.6692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9963    1.9128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2954    2.6628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5799    1.9380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6054    0.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9106   -0.3454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3063   -0.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9818    0.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4877    4.1947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1997    1.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8970    2.6820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6091    0.4256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5086   -0.3240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2034    0.4153    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1580    1.5722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2297    1.5563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0 
  4  5  1  0  0  0  0 
  5  6  2  0  0  0  0 
  6  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  8  9  1  0  0  0  0 
  8 10  1  0  0  0  0 
 10 11  2  0  0  0  0 
  5 11  1  0  0  0  0 
  1  3  1  0  0  0  0 
  3 12  2  0  0  0  0 
  3 13  1  0  0  0  0 
 13 14  1  0  0  0  0 
  2 14  1  0  0  0  0 
 15  2  1  0  0  0  0 
 16 17  1  0  0  0  0 
 17 18  2  0  0  0  0 
 17 19  2  0  0  0  0 
 17  9  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C11H14O7S/c12-9(3-6-11(13)14)7-8-1-4-10(5-2-8)18-19(15,16)17/h1-2,4-5,9,12H,3,6-7H2,(H,13,14)(H,15,16,17)

> <InChIKey>
GIYMZAJHBZLOGR-UHFFFAOYSA-N

> <Molecular_formula>
C11H14O7S

> <Major_Isotope_Mass>
290.04602378799996

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: 3p-Deydroxylation of substitued benzene (BTMR1314)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2
Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N

Biotransformation_3
Reaction Type: Lactone Hydrolysis (BTMR0259)
Enzyme(s): Unspecified bacterial lactonase
Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-8(2-4-9)7-10-5-6-11(13)14-10/h1-4,10,12H,5-7H2
Precursor InChIKey: OXASBXALVLRTKO-UHFFFAOYSA-N

Biotransformation_4
Reaction Type: 4-OH sulfonation of phenolic compound (BTMR0197)
Enzyme(s): EC 2.8.2.1
Precursor InChI: InChI=1S/C11H14O4/c12-9-3-1-8(2-4-9)7-10(13)5-6-11(14)15/h1-4,10,12-13H,5-7H2,(H,14,15)
Precursor InChIKey: JCHZTLFRWGBCDD-UHFFFAOYSA-N



$$$$

  CDK     08241813042D

 19 19  0  0  0  0  0  0  0  0999 V2000
   -1.3249   -1.5107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2953    2.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3175   -0.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3027    4.4764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6054    5.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6054    6.7200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8754    7.4700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2254    6.7200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5182    7.4807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2254    5.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8754    4.4700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6128    0.7457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0148    0.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0074    2.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5907    2.2201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8786   -0.0363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5833    0.7201    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1074    0.9878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0633   -0.6869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0 
  4  5  1  0  0  0  0 
  5  6  2  0  0  0  0 
  6  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  8  9  1  0  0  0  0 
  8 10  1  0  0  0  0 
 10 11  2  0  0  0  0 
  5 11  1  0  0  0  0 
  1  3  1  0  0  0  0 
  3 12  2  0  0  0  0 
  3 13  1  0  0  0  0 
 13 14  1  0  0  0  0 
  2 14  1  0  0  0  0 
 15  2  1  0  0  0  0 
 16 17  1  0  0  0  0 
 17 18  2  0  0  0  0 
 17 19  2  0  0  0  0 
 17 15  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C11H14O7S/c12-9-3-1-8(2-4-9)7-10(5-6-11(13)14)18-19(15,16)17/h1-4,10,12H,5-7H2,(H,13,14)(H,15,16,17)

> <InChIKey>
SQZPOLVWTPDJNK-UHFFFAOYSA-N

> <Molecular_formula>
C11H14O7S

> <Major_Isotope_Mass>
290.04602378799996

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: 3p-Deydroxylation of substitued benzene (BTMR1314)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2
Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N

Biotransformation_3
Reaction Type: Lactone Hydrolysis (BTMR0259)
Enzyme(s): Unspecified bacterial lactonase
Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-8(2-4-9)7-10-5-6-11(13)14-10/h1-4,10,12H,5-7H2
Precursor InChIKey: OXASBXALVLRTKO-UHFFFAOYSA-N

Biotransformation_4
Reaction Type: Sulfation of secondary alcohol (BTMR0502)
Enzyme(s): EC 2.8.2.2
Precursor InChI: InChI=1S/C11H14O4/c12-9-3-1-8(2-4-9)7-10(13)5-6-11(14)15/h1-4,10,12-13H,5-7H2,(H,14,15)
Precursor InChIKey: JCHZTLFRWGBCDD-UHFFFAOYSA-N



$$$$
4-Hydroxy-5-(3'-hydroxyphenyl)-valeric acid-3'-O-sulphate
  CDK     08241813042D

 19 19  0  0  0  0  0  0  0  0999 V2000
   -5.6620   -1.0206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4659   -1.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3631   -1.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8331   -1.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1322   -1.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1327    0.4790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4272    1.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7262    0.4712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7308   -1.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0311   -1.7688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4312   -1.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3633   -3.2708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0639   -1.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7650   -1.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4656    0.4786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6291   -1.7644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3288   -1.0166    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.2911    0.1341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3627    0.1308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0 
  4  5  1  0  0  0  0 
  5  6  2  0  0  0  0 
  6  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  8  9  1  0  0  0  0 
  9 10  1  0  0  0  0 
  9 11  2  0  0  0  0 
  5 11  1  0  0  0  0 
  1  3  1  0  0  0  0 
  3 12  2  0  0  0  0 
  3 13  1  0  0  0  0 
 13 14  1  0  0  0  0 
  2 14  1  0  0  0  0 
 15  2  1  0  0  0  0 
 16 17  1  0  0  0  0 
 17 18  2  0  0  0  0 
 17 19  2  0  0  0  0 
 17 10  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C11H14O7S/c12-9(4-5-11(13)14)6-8-2-1-3-10(7-8)18-19(15,16)17/h1-3,7,9,12H,4-6H2,(H,13,14)(H,15,16,17)

> <InChIKey>
DMBFBGLRQKIWGT-UHFFFAOYSA-N

> <Molecular_formula>
C11H14O7S

> <Major_Isotope_Mass>
290.04602378799996

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: 4p-Deydroxylation of substitued benzene (BTMR1012)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2
Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N

Biotransformation_3
Reaction Type: Lactone Hydrolysis (BTMR0259)
Enzyme(s): Unspecified bacterial lactonase
Precursor InChI: InChI=1S/C11H12O3/c12-9-3-1-2-8(6-9)7-10-4-5-11(13)14-10/h1-3,6,10,12H,4-5,7H2
Precursor InChIKey: VYWFHBSBNKNWSB-UHFFFAOYSA-N

Biotransformation_4
Reaction Type: 3-OH sulfonation of phenolic compound (BTMR0196)
Enzyme(s): EC 2.8.2.1
Precursor InChI: InChI=1S/C11H14O4/c12-9-3-1-2-8(6-9)7-10(13)4-5-11(14)15/h1-3,6,10,12-13H,4-5,7H2,(H,14,15)
Precursor InChIKey: CBCIWEQMPVKOHC-UHFFFAOYSA-N



$$$$
5-[4-hydroxy-3-(sulfooxy)phenyl]pentanoic acid
  CDK     08241813042D

 19 19  0  0  0  0  0  0  0  0999 V2000
    7.1407    2.3005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9446    2.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417    1.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6455    1.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6535    2.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6530    3.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9521    4.5513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2516    3.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5506    4.5505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2521    2.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5512    1.5498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9530    1.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417    0.0505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5426    2.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2436    1.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1493    1.5503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8501    2.3000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8858    3.4490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8141    3.4493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0 
  4  5  1  0  0  0  0 
  5  6  2  0  0  0  0 
  6  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  8  9  1  0  0  0  0 
  8 10  1  0  0  0  0 
 10 11  1  0  0  0  0 
 10 12  2  0  0  0  0 
  5 12  1  0  0  0  0 
  1  3  1  0  0  0  0 
  3 13  2  0  0  0  0 
  3 14  1  0  0  0  0 
 14 15  1  0  0  0  0 
  2 15  1  0  0  0  0 
 16 17  1  0  0  0  0 
 17 18  2  0  0  0  0 
 17 19  2  0  0  0  0 
 17 11  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C11H14O7S/c12-9-6-5-8(3-1-2-4-11(13)14)7-10(9)18-19(15,16)17/h5-7,12H,1-4H2,(H,13,14)(H,15,16,17)

> <InChIKey>
OUPGXCOAIUBOQD-UHFFFAOYSA-N

> <Molecular_formula>
C11H14O7S

> <Major_Isotope_Mass>
290.046023788

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: Lactone Hydrolysis (BTMR0259)
Enzyme(s): Unspecified bacterial lactonase
Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2
Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N

Biotransformation_3
Reaction Type: Dehydroxylation of 4-OH-5-phenylvaleric acid (BTMR0263)
Enzyme(s): Unspecified bacterial dehydroxylase
Precursor InChI: InChI=1S/C11H14O5/c12-8(2-4-11(15)16)5-7-1-3-9(13)10(14)6-7/h1,3,6,8,12-14H,2,4-5H2,(H,15,16)
Precursor InChIKey: JDBYFCLHVYVXCX-UHFFFAOYSA-N

Biotransformation_4
Reaction Type: 3-OH sulfonation of phenolic compound (BTMR0196)
Enzyme(s): EC 2.8.2.1
Precursor InChI: InChI=1S/C11H14O4/c12-9-6-5-8(7-10(9)13)3-1-2-4-11(14)15/h5-7,12-13H,1-4H2,(H,14,15)
Precursor InChIKey: KTDWBJGUMIZRHU-UHFFFAOYSA-N



$$$$
1,3,5-Benzenetriol, 2-[(2S)-3-(3,4-dihydroxyphenyl)-2-hydroxypropyl]-
  CDK     08241813042D

 21 22  0  0  1  0  0  0  0  0999 V2000
    1.2992   -2.7007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2992   -1.2007    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5983   -0.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8973   -1.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1968   -0.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1966    1.0501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4959   -1.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4954   -2.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7944   -3.4507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1959   -3.4516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8968   -2.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5977   -3.4514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0002   -0.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989   -1.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5984   -0.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8974   -1.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8969   -2.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1960   -3.4507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5974   -3.4516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5977   -4.9516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2984   -2.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0 
  2  3  1  0  0  0  0 
  3  4  1  0  0  0  0 
  4  5  2  0  0  0  0 
  5  6  1  0  0  0  0 
  5  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  8  9  1  0  0  0  0 
  8 10  1  0  0  0  0 
 10 11  2  0  0  0  0 
  4 11  1  0  0  0  0 
 11 12  1  0  0  0  0 
  2 13  1  0  0  0  0 
 13 14  1  0  0  0  0 
 14 15  2  0  0  0  0 
 15 16  1  0  0  0  0 
 16 17  2  0  0  0  0 
 17 18  1  0  0  0  0 
 17 19  1  0  0  0  0 
 19 20  1  0  0  0  0 
 19 21  2  0  0  0  0 
 14 21  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C15H16O6/c16-9(3-8-1-2-12(18)15(21)4-8)5-11-13(19)6-10(17)7-14(11)20/h1-2,4,6-7,9,16-21H,3,5H2/t9-/m0/s1

> <InChIKey>
OFUFTNROAPAIQL-VIFPVBQESA-N

> <Molecular_formula>
C15H16O6

> <Major_Isotope_Mass>
292.09468823199995

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0257)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N



$$$$
4-hydroxy-5-[4-hydroxy-3-(sulfooxy)phenyl]pentanoic acid
  CDK     08241813042D

 20 20  0  0  0  0  0  0  0  0999 V2000
    7.1407    2.3005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9446    2.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417    1.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6455    1.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6535    2.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6530    3.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9521    4.5513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2516    3.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5506    4.5505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2521    2.2996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5512    1.5498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9530    1.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417    0.0505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5426    2.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2436    1.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9446    3.8005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1493    1.5503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8501    2.3000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8858    3.4490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8141    3.4493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0 
  4  5  1  0  0  0  0 
  5  6  2  0  0  0  0 
  6  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  8  9  1  0  0  0  0 
  8 10  1  0  0  0  0 
 10 11  1  0  0  0  0 
 10 12  2  0  0  0  0 
  5 12  1  0  0  0  0 
  1  3  1  0  0  0  0 
  3 13  2  0  0  0  0 
  3 14  1  0  0  0  0 
 14 15  1  0  0  0  0 
  2 15  1  0  0  0  0 
 16  2  1  0  0  0  0 
 17 18  1  0  0  0  0 
 18 19  2  0  0  0  0 
 18 20  2  0  0  0  0 
 18 11  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C11H14O8S/c12-8(2-4-11(14)15)5-7-1-3-9(13)10(6-7)19-20(16,17)18/h1,3,6,8,12-13H,2,4-5H2,(H,14,15)(H,16,17,18)

> <InChIKey>
HROSNTXKMPHTSL-UHFFFAOYSA-N

> <Molecular_formula>
C11H14O8S

> <Major_Isotope_Mass>
306.040938408

> <Pathway>
Biotransformation_1
Reaction Type: Flavan-3-ol C-ring fission (BTMR0256)
Enzyme(s): Unspecified gut bacterial enzyme
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

Biotransformation_2
Reaction Type: Lactone Hydrolysis (BTMR0259)
Enzyme(s): Unspecified bacterial lactonase
Precursor InChI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2
Precursor InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N

Biotransformation_3
Reaction Type: 3-OH sulfonation of phenolic compound (BTMR0196)
Enzyme(s): EC 2.8.2.1
Precursor InChI: InChI=1S/C11H14O5/c12-8(2-4-11(15)16)5-7-1-3-9(13)10(14)6-7/h1,3,6,8,12-14H,2,4-5H2,(H,15,16)
Precursor InChIKey: JDBYFCLHVYVXCX-UHFFFAOYSA-N



$$$$
UNII-074D703K9R
  CDK     08241813042D

 25 27  0  0  1  0  0  0  0  0999 V2000
    3.8989   -1.5002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000   -0.7500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3000   -3.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6000   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6000    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8989    1.5002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000    1.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000    0.7500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8989    1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1986    0.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4975    1.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4968    3.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7957    3.7508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1971    3.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1971    5.2512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8982    3.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4962    7.5012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4962    6.0012    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.0092    4.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9734    6.2617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0 
  2  3  1  0  0  0  0 
  3  4  1  0  0  0  0 
  4  5  2  0  0  0  0 
  5  6  1  0  0  0  0 
  5  7  1  0  0  0  0 
  7  8  2  0  0  0  0 
  8  9  1  0  0  0  0 
  8 10  1  0  0  0  0 
 10 11  2  0  0  0  0 
  4 11  1  0  0  0  0 
 11 12  1  0  0  0  0 
 12 13  1  0  0  0  0 
  2 13  1  0  0  0  0 
 13 14  1  6  0  0  0 
 14 15  2  0  0  0  0 
 15 16  1  0  0  0  0 
 16 17  2  0  0  0  0 
 17 18  1  0  0  0  0 
 17 19  1  0  0  0  0 
 19 20  1  0  0  0  0 
 19 21  2  0  0  0  0 
 14 21  1  0  0  0  0 
 22 23  1  0  0  0  0 
 23 24  2  0  0  0  0 
 23 25  2  0  0  0  0 
 23 20  1  0  0  0  0 
M  END
> <InChI>
InChI=1S/C15H14O9S/c16-8-4-11(18)9-6-12(19)15(23-13(9)5-8)7-1-2-10(17)14(3-7)24-25(20,21)22/h1-5,12,15-19H,6H2,(H,20,21,22)/t12-,15-/m1/s1

> <InChIKey>
VBSMBNMUYITMLB-IUODEOHRSA-N

> <Molecular_formula>
C15H14O9S

> <Major_Isotope_Mass>
370.03585302799996

> <Pathway>
Biotransformation_1
Reaction Type: 3-OH sulfonation of phenolic compound (BTMR0196)
Enzyme(s): EC 2.8.2.1
Precursor InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
Precursor InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N



$$$$
