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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-17 08:13:33 UTC
Update Date2019-11-12 17:22:26 UTC
HMDB IDHMDB0131426
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-(3,4-dihydroxy-5-methoxyphenyl)acetic acid
Description2-(3,4-dihydroxy-5-methoxyphenyl)acetic acid belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 2-(3,4-dihydroxy-5-methoxyphenyl)acetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). It is generated by unspecified-gutmicro enzyme via an anthocyanidin-c-ring-fission-pattern3 reaction. This anthocyanidin-c-ring-fission-pattern3 occurs in human gut microbiota. 2-(3,4-dihydroxy-5-methoxyphenyl)acetic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 2-(3,4-dihydroxy-5-methoxyphenyl)-3,5,7-trihydroxy-1λ⁴-chromen-1-ylium.
Structure
Data?1563875778
Synonyms
ValueSource
2-(3,4-Dihydroxy-5-methoxyphenyl)acetateGenerator
Chemical FormulaC9H10O5
Average Molecular Weight198.174
Monoisotopic Molecular Weight198.052823422
IUPAC Name2-(3,4-dihydroxy-5-methoxyphenyl)acetic acid
Traditional Name(3,4-dihydroxy-5-methoxyphenyl)acetic acid
CAS Registry NumberNot Available
SMILES
COC1=CC(CC(O)=O)=CC(O)=C1O
InChI Identifier
InChI=1S/C9H10O5/c1-14-7-3-5(4-8(11)12)2-6(10)9(7)13/h2-3,10,13H,4H2,1H3,(H,11,12)
InChI KeyRGHMGZLQQFVXDM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
logP0.81ALOGPS
logP0.85ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.45ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.79 m³·mol⁻¹ChemAxon
Polarizability18.66 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00g4-9048100000-7f7eff873eeca23d047cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udr-1900000000-2deffe524906c575cc3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-7d1112d8f00618399516Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0900000000-2fd0333f39b62e5e8805Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ci-5900000000-410cd51a185d6e004d61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0900000000-55ab9a2044198b22d153Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f92-0900000000-073660a2e87dc58b885cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-5900000000-61033f03e4f7137d2c1cSpectrum
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 ID15853595
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound54265256
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-dihydroxy-5-methoxyphenyl)acetic acid → 2-(3-hydroxy-4,5-dimethoxyphenyl)acetic 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-dihydroxy-5-methoxyphenyl)acetic acid → 6-[4-(carboxymethyl)-2-hydroxy-6-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2-(3,4-dihydroxy-5-methoxyphenyl)acetic acid → 6-[5-(carboxymethyl)-2-hydroxy-3-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2-(3,4-dihydroxy-5-methoxyphenyl)acetic acid → 6-{[2-(3,4-dihydroxy-5-methoxyphenyl)acetyl]oxy}-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-dihydroxy-5-methoxyphenyl)acetic acid → 2-[3-hydroxy-5-methoxy-4-(sulfooxy)phenyl]acetic aciddetails