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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2023-02-21 17:29:09 UTC
HMDB IDHMDB0059631
Secondary Accession Numbers
  • HMDB59631
Metabolite Identification
Common NameCis-stilbene oxide
DescriptionCis-stilbene oxide 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. Thus, cis-stilbene oxide is considered to be an aromatic polyketide lipid molecule. Cis-stilbene oxide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1677000549
Synonyms
ValueSource
cis-alpha,Alpha'-epoxybibenzylChEBI
cis-a,Alpha'-epoxybibenzylGenerator
cis-Α,alpha'-epoxybibenzylGenerator
Stilbene oxide, trans-(+-)-isomerMeSH
Stilbene oxide, (2R-trans)-isomerMeSH
Stilbene oxide, (2S-trans)-isomerMeSH
Stilbene oxide, (cis)-isomerMeSH
trans-Stilbene oxideMeSH
Stilbene oxideMeSH
Stilbene oxide, (trans)-isomerMeSH
Chemical FormulaC14H12O
Average Molecular Weight196.2445
Monoisotopic Molecular Weight196.088815006
IUPAC Name(2R,3S)-2,3-diphenyloxirane
Traditional Namecis-stilbene oxide
CAS Registry NumberNot Available
SMILES
[H][C@]1(O[C@]1([H])C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C14H12O/c1-3-7-11(8-4-1)13-14(15-13)12-9-5-2-6-10-12/h1-10,13-14H/t13-,14+
InChI KeyARCJQKUWGAZPFX-OKILXGFUSA-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
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.015 g/LALOGPS
logP3.62ALOGPS
logP3.52ChemAxon
logS-4.1ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity59.61 m³·mol⁻¹ChemAxon
Polarizability21.09 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+144.57731661259
DarkChem[M-H]-142.27531661259
DeepCCS[M+H]+141.14930932474
DeepCCS[M-H]-138.75330932474
DeepCCS[M-2H]-172.29930932474
DeepCCS[M+Na]+147.09330932474
AllCCS[M+H]+145.232859911
AllCCS[M+H-H2O]+140.732859911
AllCCS[M+NH4]+149.432859911
AllCCS[M+Na]+150.632859911
AllCCS[M-H]-148.032859911
AllCCS[M+Na-2H]-147.632859911
AllCCS[M+HCOO]-147.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cis-stilbene oxide[H][C@]1(O[C@]1([H])C1=CC=CC=C1)C1=CC=CC=C12601.8Standard polar33892256
Cis-stilbene oxide[H][C@]1(O[C@]1([H])C1=CC=CC=C1)C1=CC=CC=C11679.6Standard non polar33892256
Cis-stilbene oxide[H][C@]1(O[C@]1([H])C1=CC=CC=C1)C1=CC=CC=C11667.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cis-stilbene oxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9400000000-4bb20476ced23354ed6e2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cis-stilbene oxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-stilbene oxide 10V, Positive-QTOFsplash10-0002-0900000000-c38f5cba131fd117556c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-stilbene oxide 20V, Positive-QTOFsplash10-0002-2900000000-aceb347ce6ec7f3ca87d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-stilbene oxide 40V, Positive-QTOFsplash10-0006-9000000000-f1ed447567a4460988062017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-stilbene oxide 10V, Negative-QTOFsplash10-0002-0900000000-4b3b0720e7148bc531122017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-stilbene oxide 20V, Negative-QTOFsplash10-0002-1900000000-809e8977ec4fdbf951442017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-stilbene oxide 40V, Negative-QTOFsplash10-00or-9600000000-d46603493ba5d6c6da2e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-stilbene oxide 10V, Negative-QTOFsplash10-0002-0900000000-ca2a4c101599ac9b00502021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-stilbene oxide 20V, Negative-QTOFsplash10-0002-3900000000-2a3d53c4bde6b23c3f912021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-stilbene oxide 40V, Negative-QTOFsplash10-0006-9300000000-72d84142d549a73ad7e82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-stilbene oxide 10V, Positive-QTOFsplash10-0002-0900000000-41030259b8ca7e8a20802021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-stilbene oxide 20V, Positive-QTOFsplash10-002b-1900000000-4459b60ff2d7546d30782021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cis-stilbene oxide 40V, Positive-QTOFsplash10-002f-9400000000-78780d2f98870f209fd92021-09-22Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC16014
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound98511
PDB IDNot Available
ChEBI ID50004
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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