Benzo[a]pyrene-4,5-oxide (PAMDB000966)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000966
Identification
Name: Benzo[a]pyrene-4,5-oxide
Description:Benzo[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
🔍MOLSDFPDBSMILESInChIView 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
Average Molecular Weight: 268.3087
Monoisotopic Molecular Weight: 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[10.7.2.0?,??0?????0?????.0??????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
Taxonomy DescriptionThis compound belongs to the class of organic compounds 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.
Kingdom Organic compounds
Super ClassBenzenoids
Class Phenanthrenes and derivatives
Sub ClassChrysenes
Direct Parent Chrysenes
Alternative Parents
Substituents
  • Chrysene
  • Naphthalene
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.57e-05 mg/mLALOGPS
logP5.24ALOGPS
logP4.52ChemAxon
logS-7.2ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity82.9 m3·mol-1ChemAxon
Polarizability29.84 Å3ChemAxon
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
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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
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 IDNot Available
HMDB IDHMDB60091
Pubchem Compound ID37786
Kegg IDC14851
ChemSpider ID34648
Wikipedia IDNot Available
BioCyc IDCPD-722
EcoCyc IDCPD-722

Enzymes

Protein Details
• GSH-dependent disulfide bond oxidoreductase
General function:
Not Available
Specific function:
Not Available
Gene Name:
yfcG
Locus Tag:
PA1033
Molecular weight:
24.5 kDa