Flavan-3-ol metabolic pathway (WP4238)

Homo sapiens

Proposed metabolic pathway of flavan-3-ols (also known as flavanols) in humans. Flavanols are derivatives of flavans and include catechin, epicatechin gallate, epigallocatechin, epigallocatechin gallate, proanthocyanidins, theaflavins, thearubigins. These compounds differ considerably not only in their structural and functional properties, but also in their metabolism and bioavailability. Green arrows indicate microbiota-mediated steps, and red arrows represent mammalian enzyme-mediated conversions. Pink arrows indicate steps that can be both microbiota- or enzyme-mediated. This pathway was developed based upon 22 papers; black arrows indicate missing information regarding the nature of conversion. Acknowledgements: This pathway is based upon work from COST Action POSITIVe, supported by COST (European Cooperation in Science and Technology).

Authors

Eirini Deligiannidou , Egon Willighagen , Denise Slenter , Kristina Hanspers , Lars Willighagen , and Eric Weitz

Activity

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Organisms

Homo sapiens

Communities

Annotations

Pathway Ontology

classic metabolic pathway

Participants

Label Type Compact URI Comment
3-(3,4-dihydroxyphenyl)propanoic acid Metabolite pubchem.compound:348454 C9H10O4
3-(3,4-dihydroxyphenyl)propanoic acid
Dihydrocaffeic acid
Theaflavin Metabolite pubchem.compound:114777 C29H24O12
Theaflavin
1-(3'-4',5-trihydroxyphenyl)-3-(2'',4'',6''-trihydroxy)propan-2-ol Metabolite pubchem.compound:21722175
(-)-Epicatechin-3'-O-glucuronide Metabolite pubchem.compound:76969982
5-(3''-4''-Dihydroxyphenyl)-gamma-valerolactone Metabolite pubchem.compound:89285 C11H12O4
5-[(3,4-dihydroxyphenyl)methyl]oxolan-2-one
Pyrogallol Metabolite pubchem.compound:1057 C6H6O3
Benzene-1,2,3-triol
4-O-Methylgallic acid Metabolite pubchem.compound:78016
(-)-Epicatechin Metabolite pubchem.compound:72276 C15H14O6
(3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
3,5,7,3',4'-Pentahydroxyflavane
Theaflavin-3-gallate Metabolite pubchem.compound:102115506 C36H28O16
(3R)-5,7-dihydroxy-2-{1,2,8-trihydroxy-9-oxo-4-[3S0-,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyron-2-yl]benzo[7]annuel-6-yl}-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate)
3-Hydroxyhippuric acid Metabolite pubchem.compound:450268 C9H9NO4
3-hydroxyhippuric acid
3-hydroxyhippuric acid
N-(3-hydroxybenzoyl)glucine
Theaflavin-3'-gallate Metabolite pubchem.compound:102115505 C36H28O16
[(2R,3R)-5,7-dihydroxy-2-[3,4,5-trihydroxy-6-oxo-1-[(2S,3S)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]benzo[7]annulen-8-yl]-3,4-dihydro-2H-chromen-3-yl]3,4,5-trihydroxybenzoate
(+)-Catechin Metabolite pubchem.compound:1203
3-Hydroxybenzoic acid Metabolite pubchem.compound:7420 C7H6O3
3-hdroxybenzoic acid
m-hydroxybenzoic acid
3-hydroxybenzenecarboxylic acid
Benzoic acid-4-sulfate Metabolite pubchem.compound:18690341 aka 4-Sulfooxybenzoic acid
4-[(10R)-3,6-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]valeric acid Metabolite chebi:52023 5(phenyl)-gamma-hydroxyvaleric acid-3'-sulfate
Dihydroferulic acid-4'-O-glucuronide Metabolite pubchem.compound:190069
3-(4'hydroxyphenyl)-propionic acid 3'-sulfate Metabolite inchikey:MIMULQQHBAZGER-UHFFFAOYSA-M AKA 3-(4'-Hydroxyphenyl)propionic acid-3'-sulfate; foudn in PhytoHub https://phytohub.eu/entries/PHUB001753
m-Coumaric acid Metabolite pubchem.compound:637541 C9H8O3
m-Coumaric acid
3-hydroxycinnamic acid
5-(3'-hydroxyphenyl)-gamma-valerolactone-4'-O-glucuronide Metabolite pubchem.compound:124202062
Dihydroferulic acid-4'-O-sulfate Metabolite pubchem.compound:187489
Pyrocatechol Metabolite pubchem.compound:289 C6H6O2
Benzene-1,2-diol
Ferulic acid-4'-O-glucuronide Metabolite pubchem.compound:6443140 C16H18O10
(2R,3R,4R,5S,6R)-6-{4-[(1E)-2-carboxyeth-1-en-1-yl]-2-methoxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
trans-Ferulic acid glucuronide
Dihydrocaffeic acid 3-sulfate Metabolite pubchem.compound:49844181
(-)Epigallocatechin Metabolite pubchem.compound:72277 C15H14O7
(2R,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol)
Isoferulic acid-3'-sulfate Metabolite pubchem.compound:71749556 C10H10O7S
(2E)-3-[4-methoxy-3-(sulfooxyphenyl]propan-2-enoic acid
Isoferulic acid-3'-O-glucuronide Metabolite pubchem.compound:49844484 C16H18O10
(2S,3S,4S,5R,6S)-6-[5-[(E)-2-carboxyethenyl]-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
5-(3',4',5'-Trihydroxyphenyl)-gamma-valerolactone Metabolite pubchem.compound:44389277 C11H12O5
5-[(3,4,5-trihydroxyphenyl)methyl]oxolan-2-one
5-[(4-hydroxyphenyl)methyl]oxolan-2-one Metabolite pubchem.compound:11550142 C11H12O3
5-[(4-hydroxyphenyl)methyl]oxolan-2-one
5-(4'-hydroxyphenyl)-gamma-valerolactone
Ferulic acid Metabolite pubchem.compound:709 C10H10O4
3-(4'-hydroxy-3-methoxyphenyl)prop-2-enoic acid
3-methylcaffeic acid
Caffeic acid Metabolite pubchem.compound:689043 C9H8O4
(E )-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
3-Phenylpropionic acid Metabolite pubchem.compound:107 C9H10O2
3-phenylpropionic acid
3-(phenyl)propionic acid
Benzenepropanoic acid
Dihydrocinnamic acid
Benzoic acid Metabolite pubchem.compound:243 C7H6O2
benzoic acid
Homovanillic acid Metabolite pubchem.compound:1738 C9H10O4
Homovanillic acid
(4-hydroxy-3-methoxyphenyl)acetic acid
3-methoxy-4-hydroxyphenylacetic acid
3-methoxy-4-hydroxyphenylacetate
3'-methoxy-4'-hydroxyphenylacetic
p-hydroxyphenylacetic acid Metabolite pubchem.compound:127
Coumaric Acid 4'-O-glucuronide Metabolite pubchem.compound:71314996
5'-(4'-hydroxyphenyl)-gamma-valerolactone-3-'sulfate Metabolite chebi:88750 Might be know under the name 5-(Hydroxyphenyl)-γ-Valerolactone-Sulfate [PMID:31694297].
3,4-Dihydroxybenzoic acid Metabolite chebi:36062 C7H6O4
3,4-Dihydroxybenzoic acid
Proteocatechuic acid
Procyanidin(Dimer) Metabolite pubchem.compound:11250133
3-Hydroxyphenyl propionic acid Metabolite pubchem.compound:91 C9H10O3
3-Hydroxyphenylpropionic acid
3-(3'-hydroxyphenyl)propionic acid
ω-Phenylacetic acid Metabolite pubchem.compound:999 C8H8O2
ω-Phenylacetic acid
Phenylacetic acid
2-phenylacetic acid
2-phenylethanoate
Hippuric acid Metabolite pubchem.compound:464 C9H9NO3
hippuric acid
N-benzoylglycine
4-hydroxy-5-(3'-hydroxyphenyl)valeric acid Metabolite pubchem.compound:52920334 AKA 5-(3'-hydroxyphenyl)-gamma-hydroxyvaleric acid; 4-Hydroxy-5-(3-hydroxyphenyl)valeric acid
Dihydroferulic acid Metabolite pubchem.compound:14340 C10H12O4
3-(4-hydroxy-3-methoxyphenyl)propanoic acid
dihydroconiferylate
5-(3,4-dihydroxyphenyl)pentanoic acid Metabolite pubchem.compound:49831816 C11H14O4
5-(3,4-dihydroxyphenyl)pentanoic acid
5-(3',4'-dihydroxyphenyl)valeric acid
Homoprotocatechuic acid Metabolite pubchem.compound:547 3',4'-Dihydroxyphenylacetic acid
Caffeic acid-3'-sulfate Metabolite pubchem.compound:102261219
1-(3,4-Dihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol Metabolite pubchem.compound:21722175
3-(3-Hydroxyphenyl)propionic acid Metabolite pubchem.compound:91 C9H10O3
3-(3-hydroxyphenyl)-propionic acid
3-(3'-hydroxyphenyl)propionic acid
3-hydroxyphenylpropionic acid
3'-hydroxy-dihydrocinnamic acid
m-hydroxy-dihydrocinnamic acid
Theaflavin-3,3'-digallate Metabolite pubchem.compound:21146795 C43H32O20
[3-hydroxy-5-oxo-4-(3,4,4-trihydroxybenzoyl)oxy-1,8-bis[(2R,3R-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]benzo[7]annulen-6-yl]3,4,5-trihydroxybenzoate
p-hydroxybenzoic acid Metabolite pubchem.compound:135 C7H6O8
4-hydroxybenzoic acid
4-hydroxybenzenecarboxylic acid
p-Coumaric acid Metabolite pubchem.compound:17450 C9H8O3
Coumaric acid
4-hydroxycinnamic acid
p-Hydroxyphenylacetic acid Metabolite pubchem.compound:127
5-(3,4,5-trihydroxyphenyl)valeric acid Metabolite pubchem.compound:101786869 AKA 5-(3,4,5-Trihydroxyphenyl)pentanoic acid (valeric is also known as pentanoic)
(+)Epiatechin Metabolite pubchem.compound:12309508
(-)-Epicatechin 3-O-gallate Metabolite pubchem.compound:65064 C22H18O11
[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl]3,4,5-trihydroxybenzoate
Epigallocatechingallate
Vanillic acid Metabolite pubchem.compound:8468 C8H8O4
vanillic acid
3-methoxy-4-hydroxybenzoic acid
p-vanillic acid
4-hydroxy-3-methoxybenzoic acid
5-(3'hydroxyphenyl)-gamma-hydroxyvaleric acid 4'-O-glucuronide Metabolite inchikey:LLKUARGHNZMSRT-UHFFFAOYNA-N AKA 5-(3'hydroxyphenyl)- gamma-hydroxyvaleric acid 4'-O-glucuronide; found in PhytoHub https://phytohub.eu/entries/PHUB001745
5-[(3-hydroxyphenyl)methyl]oxolan-2-one Metabolite pubchem.compound:3028409 C11H12O2
5-[(3-hydroxyphenyl)methyl]oxolan-2-one
5-(3'-hydroxyphenyl)-gamma-valerolactone
4-hydroxyhippuric acid Metabolite pubchem.compound:151012 C9H9NO4
[(4-hydroxyphenyl)formamido]acetic acid
4-hydroxyhippuric acid
4'-Hydroxyhippuric acid
N-(4-hydroxybenzoyl)glycine
3-(3-hydroxyphenyl)-3-hydroxypropanoic acid Metabolite pubchem.compound:102959
(S)-4-Hydroxy-5-(3,4,5-trihydroxyphenyl) valeric acid Metabolite pubchem.compound:101900149
5-(3',5')-Dihydroxyphenyl-gamma-valerolactone Metabolite hmdb:HMDB0029187
Ferulic acid-4'-sulfate Metabolite pubchem.compound:6305574 C10H10O7S
(2E)-3-[3-methoxy-4-(sulfooxy)phenyl]prop-2-enoic acid
trans-Ferulic acid sulfate
4-hydroxy-5-(3',4'-dihydroxyphenyl)valeric acid Metabolite pubchem.compound:124202072 AKA 4-Hydroxy-5-(3',4'-dihydroxyphenyl)-valeric acid-O-glucuronide
Isoferulic acid Metabolite pubchem.compound:736189 C10H10O4
(E )-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid
4-methylcaffeic acid
Gallic acid Metabolite pubchem.compound:370 C7H6O5
3,4,5-trihydroxybenzoic acid
(S)-4-hydroxy-5-(3,5-dihydroxyphenyl) valeric acid Metabolite pubchem.compound:101900150
5-(Hydroxyphenyl)-gamma-valerolactone-O-sulphate Metabolite hmdb:HMDB0059993
3-(4'-hydroxyphenyl)propionic acid Metabolite pubchem.compound:91
p-hydroxybenzoic acid Metabolite pubchem.compound:135 C7H6O8
p-hydroxybenzoic acid
4-hydroxybenzoic acid
4-hydroxybenzenecarboxylic acid
Benzoic acid-4-sulfate Metabolite pubchem.compound:18690341 AKA 4-Sulfooxybenzoic acid
4-Hydroxyhippuric acid Metabolite pubchem.compound:151012 C9H9NO4
[(4-hydroxyphenyl)formamido]acetic acid
4-Hydroxyhippuric acid
4'-Hydroxyhippuric acid
N-(4-hydroxybenzoyl)glycine
Homovanillic acid Metabolite pubchem.compound:1738 C9H10O4
Homovanillic acid
(4-hydroxy-3-methoxyphenyl)acetic acid
3-methoxy-4-hydroxyphenylacetic acid
3-methoxy-4-hydroxyphenylacetate
3'-methoxy-4'-hydroxyphenylacetic
1-(3',4'-Dihydroxyphenyl)-3-(2'',4''-6''-trihydroxyphenyl)propan-2-ol Metabolite pubchem.compound:21722175 C15H16O6
2-[3-(3,4-dihydroxyphenyl)-2-hydroxypropyl]benzene-1,3,5-triol
Catechin Metabolite pubchem.compound:1203 C15H14O6
2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
3-(3-Hydroxyphenyl)propionic acid Metabolite pubchem.compound:91 C9H10O3
3-(3-hydroxyphenyl)-propionic acid
3-(3'-hydroxyphenyl)propionic acid
3-hydroxyphenylpropionic acid
3'-hydroxy-dihydrocinnamic acid
m-hydroxy-dihydrocinnamic acid
3-(4'-Hydroxyphenyl)propionic acid Metabolite pubchem.compound:91
CoA Metabolite chebi:15346
4-Hydroxybenzoic acid 3-sulfate Metabolite pubchem.compound:76974408
Gallocatechin Metabolite pubchem.compound:65084 C15H14O7
(2R,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol)
4-Hydroxyhippuric acid Metabolite pubchem.compound:151012 C9H9NO4
[(4-hydroxyphenyl)formamido]acetic acid
4-Hydroxyhippuric acid
4'-Hydroxyhippuric acid
N-(4-hydroxybenzoyl)glycine
3-Hydroxyhippuric acid Metabolite pubchem.compound:450268 C9H9NO4
3-hydroxyhippuric acid
3-hydroxyhippuric acid
N-(3-hydroxybenzoyl)glucine
3-Hydroxybenzoic acid Metabolite pubchem.compound:7420 C7H6O3
3-hdroxybenzoic acid
m-hydroxybenzoic acid
3-hydroxybenzenecarboxylic acid
3-O-Methylgallic acid Metabolite chebi:28647
Pyrogallol-1-sulfate Metabolite pubchem.compound:54110629
Pyrogallol-2-O-glucuronide Metabolite pubchem.compound:122553541
Pyrogallol-2-sulfate Metabolite pubchem.compound:92013662
(-)-Epicatechin-3'-sulfate Metabolite pubchem.compound:124202088
Catechol-O-methyltransferase GeneProduct ensembl:ENSG00000093010
UDP-glucuronyltransferase Protein eccode:2.4.1.17

References

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