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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-18 15:51:49 UTC
Update Date2019-11-12 17:23:27 UTC
HMDB IDHMDB0135757
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-[2-(2-hydroxyphenyl)ethyl]-3-methoxybenzene-1,2-diol
Description5-[2-(2-hydroxyphenyl)ethyl]-3-methoxybenzene-1,2-diol belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. 5-[2-(2-hydroxyphenyl)ethyl]-3-methoxybenzene-1,2-diol is an extremely weak basic (essentially neutral) compound (based on its pKa). This hydroxylation-of-benzene-ortho-to-strongly-edg occurs in humans. It is generated by cyp2a6 and cyp2e1 enzymes via a hydroxylation-of-benzene-ortho-to-strongly-edg reaction. 5--3-methoxybenzene-1,2-diol is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 3--5-methoxyphenol.
Structure
Data?1563876414
SynonymsNot Available
Chemical FormulaC15H16O4
Average Molecular Weight260.289
Monoisotopic Molecular Weight260.104858995
IUPAC Name5-[2-(2-hydroxyphenyl)ethyl]-3-methoxybenzene-1,2-diol
Traditional Name5-[2-(2-hydroxyphenyl)ethyl]-3-methoxybenzene-1,2-diol
CAS Registry NumberNot Available
SMILES
COC1=CC(CCC2=CC=CC=C2O)=CC(O)=C1O
InChI Identifier
InChI=1S/C15H16O4/c1-19-14-9-10(8-13(17)15(14)18)6-7-11-4-2-3-5-12(11)16/h2-5,8-9,16-18H,6-7H2,1H3
InChI KeyOXJLPHGSBKKLIB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Catechol
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Ether
  • Organic oxygen compound
  • 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
logP2.46ALOGPS
logP3.44ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)9.58ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.92 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.8 m³·mol⁻¹ChemAxon
Polarizability27.61 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-03k9-4110900000-b04838db11fcd1d0baddSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zfr-2910000000-9dfa55c022bd4c75cf00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0190000000-0bcf956372cf67da1263Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0r00-0930000000-8ec12798b533aca9d170Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a7j-7920000000-625ca83b4d0a79567ae6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-fa1a7304a07cf9905b95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0090000000-ef0ca5c398525bab2c25Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-2950000000-d95bed6c16c6304a3153Spectrum
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 Compound131839256
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
5-[2-(2-hydroxyphenyl)ethyl]-3-methoxybenzene-1,2-diol → 5-[2-(2-hydroxyphenyl)ethyl]-2,3-dimethoxyphenoldetails
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
5-[2-(2-hydroxyphenyl)ethyl]-3-methoxybenzene-1,2-diol → 3,4,5-trihydroxy-6-{2-hydroxy-4-[2-(2-hydroxyphenyl)ethyl]-6-methoxyphenoxy}oxane-2-carboxylic aciddetails
5-[2-(2-hydroxyphenyl)ethyl]-3-methoxybenzene-1,2-diol → 3,4,5-trihydroxy-6-{2-hydroxy-5-[2-(2-hydroxyphenyl)ethyl]-3-methoxyphenoxy}oxane-2-carboxylic aciddetails
5-[2-(2-hydroxyphenyl)ethyl]-3-methoxybenzene-1,2-diol → 6-{2-[2-(3,4-dihydroxy-5-methoxyphenyl)ethyl]phenoxy}-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
5-[2-(2-hydroxyphenyl)ethyl]-3-methoxybenzene-1,2-diol → {2-hydroxy-4-[2-(2-hydroxyphenyl)ethyl]-6-methoxyphenyl}oxidanesulfonic aciddetails