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benzil (YMDB00136)

Identification
YMDB IDYMDB00136
Namebenzil
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionbenzil, also known as bibenzoyl or diphenylglyoxal, 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. benzil is an extremely weak basic (essentially neutral) compound (based on its pKa). benzil may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1, 2-Diphenylethane-1,2-dione
  • 1,2-Diphenylethane-1,2-dione
  • 1,2-Diphenylethanedione
  • Benzil (1,2-diphenylethan-dion)
  • Benzilone bomide
  • Benzilonium bromide
  • Bibenzoyl
  • Chlorobenzilate
  • Dibenzoyl
  • Diphenyl-α
  • Diphenyl-alpha,beta-diketone
  • Diphenylethanedione
  • Diphenylglyoxal
  • Ethanedione, diphenyl-
  • Ethyl 2-hydroxy-2,2-bis(4-chlorophenyl)acetate
  • Ethyl-4,4'-dichlorobenzilate
  • Glyoxal, diphenyl-
  • Diphenyl-alpha-beta-ketone
  • Diphenylethane-1,2-dione
CAS number134-81-6
WeightAverage: 210.228
Monoisotopic: 210.068079564
InChI KeyWURBFLDFSFBTLW-UHFFFAOYSA-N
InChIInChI=1S/C14H10O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10H
IUPAC Namediphenylethane-1,2-dione
Traditional IUPAC Namebenzil
Chemical FormulaC14H10O2
SMILESO=C(C(=O)C1=CC=CC=C1)C1=CC=CC=C1
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
  • Aryl ketone
  • Benzoyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Alpha-diketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point94.8 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogP3.38 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.034 g/LALOGPS
logP2.96ALOGPS
logP3.24ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)-8.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity62.07 m³·mol⁻¹ChemAxon
Polarizability22.38 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm, Plasma Membrane
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0900000000-f7ce6301421d3df5beb7JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0190000000-bffd62dacd93083a9a20JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-0950000000-dcbbbbd0401431287205JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-2eb1f37fb40cf4966e2fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-ff923ab42ee3951098feJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0190000000-439530eec2245cd948faJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-1900000000-086ca8597f4e6bf07887JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-14a0ab532416bab774e5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-9ace76c08b1ad8506b69JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-5900000000-cdf41ea6802159be9ed3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-5a057e6d2cbfd354e8b0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-3970000000-2890cfc63a1853074084JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-9440000000-1a63d3b2b8e263fd282dJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Maruyama, R., Nishizawa, M., Itoi, Y., Ito, S., Inoue, M. (2001). "Isolation and expression of a Bacillus cereus gene encoding benzil reductase." Biotechnol Bioeng 75:630-633.11745140
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID51507
HMDB IDNot Available
Pubchem Compound ID8651
Kegg IDC14574
ChemSpider ID8329
FOODB IDNot Available
WikipediaBenzil
BioCyc IDNot Available

Enzymes

Protein Details
1. Benzil reductase IRC24
General function:
Involved in oxidoreductase activity
Specific function:
Reduces benzil stereospecifically to (S)-benzoin. Is probably involved in a pathway contributing to genomic integrity
Gene Name:
IRC24
Uniprot ID:
P40580
Molecular weight:
28803.90039
Reactions
Benzoin + NADP(+) → benzil + NADPH.