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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-19 18:47:17 UTC
Update Date2019-11-12 17:23:39 UTC
HMDB IDHMDB0141791
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-[3-(3,5-dihydroxyphenyl)oxiran-2-yl]benzene-1,2-diol
Description4-[3-(3,5-dihydroxyphenyl)oxiran-2-yl]benzene-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. 4-benzene-1,2-diol is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 4-benzene-1,2-diol. 4-[3-(3,5-dihydroxyphenyl)oxiran-2-yl]benzene-1,2-diol is an extremely weak basic (essentially neutral) compound (based on its pKa). It is generated by cyp2e1 enzyme via an alkene-epoxidation-pattern1 reaction. This alkene-epoxidation-pattern1 occurs in humans.
Structure
Data?1563877364
SynonymsNot Available
Chemical FormulaC14H12O5
Average Molecular Weight260.245
Monoisotopic Molecular Weight260.068473486
IUPAC Name4-[3-(3,5-dihydroxyphenyl)oxiran-2-yl]benzene-1,2-diol
Traditional Name4-[3-(3,5-dihydroxyphenyl)oxiran-2-yl]benzene-1,2-diol
CAS Registry NumberNot Available
SMILES
OC1=CC(=CC(O)=C1)C1OC1C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C14H12O5/c15-9-3-8(4-10(16)6-9)14-13(19-14)7-1-2-11(17)12(18)5-7/h1-6,13-18H
InChI KeyFTPBQRXLHKCKEQ-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
  • Catechol
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
logP1.49ALOGPS
logP2.31ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)8.84ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area93.45 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity67.53 m³·mol⁻¹ChemAxon
Polarizability25.56 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0ue9-1090230000-34b85e266a4a9e07ba18Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1910000000-dd7bb8ac4f34d2a307fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-6e723c5b0e92b39f783cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ki-0950000000-bf6a5a37dd91c643d955Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-5910000000-dc5ea65be43cffce0dd1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0390000000-ddfb3dcc6e51ff33d091Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0950000000-ec32c4d31b7f3f972ec3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1910000000-fc39665cf4f9d649b8fdSpectrum
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 Compound131839527
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
4-[3-(3,5-dihydroxyphenyl)oxiran-2-yl]benzene-1,2-diol → 5-[3-(4-hydroxy-3-methoxyphenyl)oxiran-2-yl]benzene-1,3-dioldetails
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
4-[3-(3,5-dihydroxyphenyl)oxiran-2-yl]benzene-1,2-diol → 6-{3-[3-(3,4-dihydroxyphenyl)oxiran-2-yl]-5-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
4-[3-(3,5-dihydroxyphenyl)oxiran-2-yl]benzene-1,2-diol → 6-{4-[3-(3,5-dihydroxyphenyl)oxiran-2-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
4-[3-(3,5-dihydroxyphenyl)oxiran-2-yl]benzene-1,2-diol → 6-{5-[3-(3,5-dihydroxyphenyl)oxiran-2-yl]-2-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Regulates negatively CDK5 activity via p25/p35 translocation to prevent neurodegeneration.
Gene Name:
GSTP1
Uniprot ID:
P09211
Molecular weight:
23355.625
Reactions
4-[3-(3,5-dihydroxyphenyl)oxiran-2-yl]benzene-1,2-diol → 2-amino-4-({1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-{[1-(3,4-dihydroxyphenyl)-2-(3,5-dihydroxyphenyl)-2-hydroxyethyl]sulfanyl}ethyl}-C-hydroxycarbonimidoyl)butanoic aciddetails
4-[3-(3,5-dihydroxyphenyl)oxiran-2-yl]benzene-1,2-diol → 2-amino-4-({1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-{[2-(3,4-dihydroxyphenyl)-1-(3,5-dihydroxyphenyl)-2-hydroxyethyl]sulfanyl}ethyl}-C-hydroxycarbonimidoyl)butanoic 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
4-[3-(3,5-dihydroxyphenyl)oxiran-2-yl]benzene-1,2-diol → {5-[3-(3,5-dihydroxyphenyl)oxiran-2-yl]-2-hydroxyphenyl}oxidanesulfonic aciddetails