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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:19:23 UTC
Update Date2020-02-26 21:36:53 UTC
HMDB IDHMDB0012111
Secondary Accession Numbers
  • HMDB12111
Metabolite Identification
Common Name(+)-(1R,2R)-1,2-Diphenylethane-1,2-diol
Description(+)-(1R,2R)-1,2-Diphenylethane-1,2-diol, also known as (1R,2R)-hydrobenzoin, 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 (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol is an extremely weak basic (essentially neutral) compound (based on its pKa). This is a key hepatic enzyme that is involved in the metabolism of numerous xenobiotics, such as 1,3-butadiene oxide, styrene oxide and the polycyclic aromatic hydrocarbon benzopyrene 4,5-oxide.
Structure
Data?1582753013
Synonyms
ValueSource
(+)-HydrobenzoinChEBI
(1R,2R)-HydrobenzoinChEBI
(R,R)-(+)-HydrobenzoinChEBI
(+)-(1R,2R)-1,2-Diphenylethane-1,2-diolChEBI
Chemical FormulaC14H14O2
Average Molecular Weight214.2598
Monoisotopic Molecular Weight214.099379692
IUPAC Name(1R,2R)-1,2-diphenylethane-1,2-diol
Traditional Name(+)-hydrobenzoin
CAS Registry Number52340-78-0
SMILES
O[C@@H]([C@H](O)C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C14H14O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-16H/t13-,14-/m1/s1
InChI KeyIHPDTPWNFBQHEB-ZIAGYGMSSA-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
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • 1,2-diol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.48 g/LALOGPS
logP2.05ALOGPS
logP2.36ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)13.08ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity63.12 m³·mol⁻¹ChemAxon
Polarizability22.85 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 (Non-derivatized) - 70eV, Positivesplash10-0a4i-5900000000-394061468aba8a77892dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-2920000000-fc1221353fb61e845a68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0290000000-a262606cc49f18a8a839Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-1940000000-fadcef7404e01b142764Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-9300000000-95ff5df80e838be0f134Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-cdff589dfb8ea36de40cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-9360000000-66e82b42c9eca1c9961aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-05181718f5122f0c81f3Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDFDB028775
KNApSAcK IDNot Available
Chemspider ID745456
KEGG Compound IDC16015
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound853019
PDB IDNot Available
ChEBI ID50014
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Biotransformation enzyme that catalyzes the hydrolysis of arene and aliphatic epoxides to less reactive and more water soluble dihydrodiols by the trans addition of water.
Gene Name:
EPHX1
Uniprot ID:
P07099
Molecular weight:
52948.48
Reactions
Cis-stilbene oxide + Water → (+)-(1R,2R)-1,2-Diphenylethane-1,2-dioldetails