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Benzo[a]pyrene-4,5-oxide (M2MDB000966)

Record Information
Version2.0
Creation Date2012-05-31 14:28:26 -0600
Update Date2015-06-03 17:19:21 -0600
Secondary Accession Numbers
  • ECMDB20118
Identification
Name:Benzo[a]pyrene-4,5-oxide
DescriptionBenzo[a]pyrene-4,5-oxide is a member of the chemical class known as Chrysenes. These are compounds containing the polyaromatic chrysene moiety, which consists of a benzene ring fused to a phenanthrene ring system to form Benzo[a]phenanthrene. In the absence of the ycbX- and yiiM-dependent pathways, biotin sulfoxide reductase plays also a role in the detoxification pathway. (PMID 18312271)
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • (+)-3b,4a-dihydrobenzo(1,2)pyreno(4,5-b)Oxirene
  • (+)-3beta,4alpha-Dihydrobenzo(1,2)pyreno(4,5-b)oxirene
  • (+)-3β,4α-dihydrobenzo(1,2)pyreno(4,5-b)Oxirene
  • (+-)-3b,4a-dihydrobenzo(1,2)pyreno(4,5-b)Oxirene
  • (+-)-3beta,4alpha-Dihydrobenzo(1,2)pyreno(4,5-b)oxirene
  • (+-)-3β,4α-dihydrobenzo(1,2)pyreno(4,5-b)Oxirene
  • 1H-thieno(3,4-D)Imidazole-4-pentanoate, hexahydro-2-oxo-, 5-oxide, (3as,4S,5S,6ar)-
  • 1H-thieno(3,4-D)Imidazole-4-pentanoate, hexahydro-2-oxo-, 5-oxide, (3as-(3aα,4β,5α,6aα))-
  • 1H-thieno(3,4-d)imidazole-4-pentanoic acid, hexahydro-2-oxo-, 5-oxide, (3aS,4S,5S,6aR)-
  • 1H-thieno(3,4-d)imidazole-4-pentanoic acid, hexahydro-2-oxo-, 5-oxide, (3aS-(3aα,4β,5α,6aα))-
  • 3b,4a-dihydro-(+)-benzo(1,2)pyreno(4,5-b)Oxirene
  • 3b,4a-dihydro-(+-)-benzo(1,2)pyreno(4,5-b)Oxirene
  • 3b,4a-dihydro-(3BR-cis)-benzo(1,2)pyreno(4,5-b)Oxirene
  • 3b,4a-dihydro-benzo(1,2)pyreno(4,5-b)Oxirene
  • 3b,4a-dihydrobenzo[1,2]pyreno[4,5-b]Oxirene
  • 3beta,4alpha-dihydro-(+)-Benzo(1,2)pyreno(4,5-b)oxirene
  • 3beta,4alpha-dihydro-(+-)-Benzo(1,2)pyreno(4,5-b)oxirene
  • 3beta,4alpha-dihydro-(3bR-cis)-Benzo(1,2)pyreno(4,5-b)oxirene
  • 3beta,4alpha-dihydro-Benzo(1,2)pyreno(4,5-b)oxirene
  • 3beta,4alpha-Dihydrobenzo[1,2]pyreno[4,5-b]oxirene
  • 3β,4α-dihydro-(+)-benzo(1,2)pyreno(4,5-b)Oxirene
  • 3β,4α-dihydro-(+-)-benzo(1,2)pyreno(4,5-b)Oxirene
  • 3β,4α-dihydro-(3BR-cis)-benzo(1,2)pyreno(4,5-b)Oxirene
  • 3β,4α-dihydro-benzo(1,2)pyreno(4,5-b)Oxirene
  • 3β,4α-dihydrobenzo[1,2]pyreno[4,5-b]Oxirene
  • 4,5-Dihydro-4,5-epoxybenzpyrene
  • 4,5-Dihydrobenzo(a)pyrene-4,5-epoxide
  • Benz(a)pyrene 4,5-oxide
  • Benzo(a)pyrene 4,5-epoxide
  • BENZO(a)PYRENE 4,5-OXIDE
  • Benzo(a)pyrene-4,5-epoxide
  • Benzo(a)pyrene-4,5-oxide
  • Benzo[a]pyrene-4,5-epoxide
  • Biotin sulfoxide
  • Biotin sulphoxide
  • Bp 4,5-epoxide
  • Bp 4,5-oxide
  • Hexahydro-2-oxo-5-oxide(3aS,4S,5S,6aR)-1H-Thieno(3,4-D)imidazole-4-pentanoate
  • Hexahydro-2-oxo-5-oxide(3aS,4S,5S,6aR)-1H-Thieno(3,4-D)imidazole-4-pentanoic acid
  • hexahydro-2-oxo-5-Oxide(3as-(3aalpha,4b,5a,6aalpha))-1H-thieno(3,4-D)imidazole-4-pentanoate
  • hexahydro-2-oxo-5-Oxide(3as-(3aalpha,4b,5a,6aalpha))-1H-thieno(3,4-D)imidazole-4-pentanoic acid
  • Hexahydro-2-oxo-5-oxide(3aS-(3aalpha,4beta,5alpha,6aalpha))-1H-Thieno(3,4-D)imidazole-4-pentanoate
  • Hexahydro-2-oxo-5-oxide(3aS-(3aalpha,4beta,5alpha,6aalpha))-1H-Thieno(3,4-D)imidazole-4-pentanoic acid
  • hexahydro-2-oxo-5-Oxide(3as-(3aalpha,4β,5α,6aalpha))-1H-thieno(3,4-D)imidazole-4-pentanoate
  • hexahydro-2-oxo-5-Oxide(3as-(3aalpha,4β,5α,6aalpha))-1H-thieno(3,4-D)imidazole-4-pentanoic acid
Chemical Formula:C20H12O
Weight:Average: 268.3087
Monoisotopic: 268.088815006
InChI Key:XGZQLNASOQVQTD-UHFFFAOYSA-N
InChI:InChI=1S/C20H12O/c1-2-6-13-12(4-1)10-16-18-14(13)9-8-11-5-3-7-15(17(11)18)19-20(16)21-19/h1-10,19-20H
CAS number:37574-47-3
IUPAC Name:18-oxahexacyclo[10.7.2.0³,⁸.0⁹,²⁰.0¹⁶,²¹.0¹⁷,¹⁹]henicosa-1,3,5,7,9(20),10,12(21),13,15-nonaene
Traditional IUPAC Name:benzo(a)pyrene 4,5-oxide
SMILES:O1C2C1C1=CC3=CC=CC=C3C3=C1C1=C(C=CC=C21)C=C3
Chemical Taxonomy
Description belongs to the class of organic compounds known as chrysenes. Chrysenes are compounds containing the polyaromatic chrysene moiety, which consists of a benzene ring fused to a phenanthrene ring system to form Benzo[a]phenanthrene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassChrysenes
Direct ParentChrysenes
Alternative Parents
Substituents
  • Chrysene
  • Naphthalene
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.6e-05 g/LALOGPS
logP5.24ALOGPS
logP4.52ChemAxon
logS-7.2ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity82.9 m³·mol⁻¹ChemAxon
Polarizability29.84 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
Benzo[a]pyrene-4,5-oxide + Glutathione <> 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene
Benzo[a]pyrene-4,5-oxide + Red-Thioredoxin Biotin + Water + Ox-Thioredoxin
SMPDB Pathways:
glutathione metabolism IIIPW002018 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-0090000000-a0acee16644b56de8a87View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-a5fc140110d675a8f67fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0090000000-265bb670b8409fa79f1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufu-1090000000-8be0bcddc8e600a81d8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-a54043fd1ab8580b6ed2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-9869044ce7dbcc294175View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ou-0090000000-ebe5c29fe92744c28350View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Kozmin, S. G., Leroy, P., Pavlov, Y. I., Schaaper, R. M. (2008). "YcbX and yiiM, two novel determinants for resistance of Escherichia coli to N-hydroxylated base analogues." Mol Microbiol 68:51-65. Pubmed: 18312271
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID34560
HMDB IDHMDB0060091
Pubchem Compound ID37786
Kegg IDC14851
ChemSpider ID34648
Wikipedia IDNot Available
BioCyc IDCPD-722
EcoCyc IDCPD-722

Enzymes

Protein Details
1. Glutathione S-transferase
General function:
Involved in protein binding
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles
Gene Name:
gst
Uniprot ID:
P0A9D2
Molecular weight:
22868
Reactions
RX + glutathione = HX + R-S-glutathione.
Protein Details
2. Biotin sulfoxide reductase
General function:
Involved in oxidoreductase activity
Specific function:
This enzyme may serve as a scavenger, allowing the cell to utilize biotin sulfoxide as a biotin source. It reduces a spontaneous oxidation product of biotin, D-biotin D-sulfoxide (BSO or BDS), back to biotin
Gene Name:
bisC
Uniprot ID:
P20099
Molecular weight:
85850
Protein Details
3. GSH-dependent disulfide bond oxidoreductase
General function:
Not Available
Specific function:
Not Available
Gene Name:
yfcG
Uniprot ID:
P77526
Molecular weight:
Not Available