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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-18 10:39:31 UTC
Update Date2019-11-12 17:23:14 UTC
HMDB IDHMDB0135063
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-(3,4-dihydroxyphenyl)-8-[1-(2,4-dihydroxyphenyl)-2-hydroxy-3-(3-hydroxyphenyl)propyl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Description2-(3,4-dihydroxyphenyl)-8-[1-(2,4-dihydroxyphenyl)-2-hydroxy-3-(3-hydroxyphenyl)propyl]-3,4-dihydro-2h-1-benzopyran-3,5,7-triol is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 2-(3,4-dihydroxyphenyl)-8-[1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-2-hydroxypropyl]-3,4-dihydro-2h-1-benzopyran-3,5,7-triol. It is generated by Dehydroxylase enzyme via a -4p-dehydroxylation-of-substituted-benzene reaction. This -4p-dehydroxylation-of-substituted-benzene occurs in human gut microbiota.
Structure
Data?1563876313
SynonymsNot Available
Chemical FormulaC30H28O10
Average Molecular Weight548.544
Monoisotopic Molecular Weight548.168247102
IUPAC Name2-(3,4-dihydroxyphenyl)-8-[1-(2,4-dihydroxyphenyl)-2-hydroxy-3-(3-hydroxyphenyl)propyl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Name2-(3,4-dihydroxyphenyl)-8-[1-(2,4-dihydroxyphenyl)-2-hydroxy-3-(3-hydroxyphenyl)propyl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
CAS Registry NumberNot Available
SMILES
OC(CC1=CC(O)=CC=C1)C(C1=C(O)C=C(O)C=C1)C1=C(O)C=C(O)C2=C1OC(C(O)C2)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C30H28O10/c31-16-3-1-2-14(8-16)9-24(37)27(18-6-5-17(32)11-21(18)34)28-25(38)13-22(35)19-12-26(39)29(40-30(19)28)15-4-7-20(33)23(36)10-15/h1-8,10-11,13,24,26-27,29,31-39H,9,12H2
InChI KeyNPOOLOAVULDAOA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentCatechins
Alternative Parents
Substituents
  • Catechin
  • Linear 1,7-diphenylheptane skeleton
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Cinnamylphenol
  • Linear 1,3-diarylpropanoid
  • 1-benzopyran
  • Chromane
  • Benzopyran
  • Resorcinol
  • Catechol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary alcohol
  • Organoheterocyclic compound
  • Polyol
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.45ALOGPS
logP3.98ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)8.1ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area191.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity145.12 m³·mol⁻¹ChemAxon
Polarizability53.61 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-5830329000-7f636fa6fd49bbee5be6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08fr-0900820000-cb73de74294543be6db9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0104090000-677c847d98aa5c23e280Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05c2-0519460000-357385d9d041ce97e64cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-1794130000-22d75442c34403f3d088Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0101090000-77525a41463e43d82183Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pba-0931040000-2c0bf897383792ad5683Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0951000000-d6d3561174b7f7aefb50Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131838734
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Djoumbou Feunang, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
2-(3,4-dihydroxyphenyl)-8-[1-(2,4-dihydroxyphenyl)-2-hydroxy-3-(3-hydroxyphenyl)propyl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol → 8-[1-(2,4-dihydroxyphenyl)-2-hydroxy-3-(3-hydroxyphenyl)propyl]-2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-trioldetails
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
2-(3,4-dihydroxyphenyl)-8-[1-(2,4-dihydroxyphenyl)-2-hydroxy-3-(3-hydroxyphenyl)propyl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol → {[1-(2,4-dihydroxyphenyl)-1-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-3-(3-hydroxyphenyl)propan-2-yl]oxy}sulfonic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
2-(3,4-dihydroxyphenyl)-8-[1-(2,4-dihydroxyphenyl)-2-hydroxy-3-(3-hydroxyphenyl)propyl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol → 6-{[2-(3,4-dihydroxyphenyl)-8-[1-(2,4-dihydroxyphenyl)-2-hydroxy-3-(3-hydroxyphenyl)propyl]-3,5-dihydroxy-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2-(3,4-dihydroxyphenyl)-8-[1-(2,4-dihydroxyphenyl)-2-hydroxy-3-(3-hydroxyphenyl)propyl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol → 6-{3-[3-(2,4-dihydroxyphenyl)-3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-2-hydroxypropyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2-(3,4-dihydroxyphenyl)-8-[1-(2,4-dihydroxyphenyl)-2-hydroxy-3-(3-hydroxyphenyl)propyl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol → 6-(4-{1-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-2-hydroxy-3-(3-hydroxyphenyl)propyl}-3-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2-(3,4-dihydroxyphenyl)-8-[1-(2,4-dihydroxyphenyl)-2-hydroxy-3-(3-hydroxyphenyl)propyl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol → 6-(2-{1-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-2-hydroxy-3-(3-hydroxyphenyl)propyl}-5-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2-(3,4-dihydroxyphenyl)-8-[1-(2,4-dihydroxyphenyl)-2-hydroxy-3-(3-hydroxyphenyl)propyl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol → 6-(5-{8-[1-(2,4-dihydroxyphenyl)-2-hydroxy-3-(3-hydroxyphenyl)propyl]-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl}-2-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
2-(3,4-dihydroxyphenyl)-8-[1-(2,4-dihydroxyphenyl)-2-hydroxy-3-(3-hydroxyphenyl)propyl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol → {3-[3-(2,4-dihydroxyphenyl)-3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-2-hydroxypropyl]phenyl}oxidanesulfonic aciddetails
2-(3,4-dihydroxyphenyl)-8-[1-(2,4-dihydroxyphenyl)-2-hydroxy-3-(3-hydroxyphenyl)propyl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol → (5-{8-[1-(2,4-dihydroxyphenyl)-2-hydroxy-3-(3-hydroxyphenyl)propyl]-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl}-2-hydroxyphenyl)oxidanesulfonic aciddetails