Benzo[a]pyrene-7,8-diol (PAMDB000967)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000967
Identification
Name: Benzo[a]pyrene-7,8-diol
Description:Benzo[a]pyrene-7,8-diol is a member of the chemical class known as Pyrenes. These are compounds containing a pyrene moiety, which consists four fused benzene rings, resulting in a flat aromatic system. Benzo[a]pyrene-7,8-dihydrodiol 9,10-epoxide (BPDE), a metabolite of the widespread environmental pollutant benzo[a]pyrene, is a mutagenic in both bacterial and mammalian systems. (PMID 7890605)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (E)-3,7-dimethylocta-1,6-dien-3,8-diol
  • (E)-Benzo(a)pyrene-7,8-dihydrodiol
  • 7,8-Dihydro 7,8-dihydroxybenzo(a)pyrene
  • 7,8-Dihydro-7,8-dihydroxy-(E)-Benzo(a)pyrene
  • 7,8-Dihydro-7,8-dihydroxy-Benzo(a)pyrene
  • 7,8-Dihydro-7,8-dihydroxybenzopyrene
  • 7,8-Dihydrobenzo(a)pyrene-7,8-diol
  • 7,8-Dihydroxy-7,8-dihydrobenzo(a)pyrene
  • 7,8-Diol-benzo(a)pyrene
  • Benzo(a)pyrene 7,8-dihydrodiol
  • Benzo(a)pyrene 7,8-dihydrodiol, (7R-trans)-isomer
  • Benzo(a)pyrene 7,8-dihydrodiol, (7S-trans)-isomer
  • Benzo(a)pyrene 7,8-dihydrodiol, (cis)-isomer
  • Benzo(a)pyrene 7,8-dihydrodiol, (trans)-(+-)-isomer
  • Benzo(a)pyrene 7,8-dihydrodiol, (trans)-isomer
  • Benzo(a)pyrene 7,8-diol
  • Benzo(a)pyrene-7,8-dihydrodiol
  • Benzo(a)pyrene-7,8-diol
  • Benzopyrene-7,8-dihydrodiol
  • Benzo[a]pyrene-7,8-dihydrodiol
  • BP-7,8 diol
  • BP-7,8-dihydrodiol
  • Cis-7,8-Dihydrobenzo[a]pyrendiol
  • Trans-7,8-Dihydroxy-7,8-dihydrobenzo(a)pyrene
  • Trans-Benzopyrene 7,8-dihydrodiol
Chemical Formula: C20H14O2
Average Molecular Weight: 286.324
Monoisotopic Molecular Weight: 286.099379692
InChI Key: YDXRLMMGARHIIC-UHFFFAOYSA-N
InChI:InChI=1S/C20H14O2/c21-17-9-8-14-15-7-6-12-3-1-2-11-4-5-13(19(15)18(11)12)10-16(14)20(17)22/h1-10,17,20-22H
CAS number: 13345-25-0
IUPAC Name:pentacyclo[10.6.2.0?,??0?????0??????icosa-1,3,7,9(19),10,12(20),13,15,17-nonaene-5,6-diol
Traditional IUPAC Name: benzo(a)pyrene 7,8-diol
SMILES:OC1C=CC2=C3C=CC4=CC=CC5=C4C3=C(C=C5)C=C2C1O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as pyrenes. These are compounds containing a pyrene moiety, which consists four fused benzene rings, resulting in a flat aromatic system.
Kingdom Organic compounds
Super ClassBenzenoids
Class Pyrenes
Sub ClassNot Available
Direct Parent Pyrenes
Alternative Parents
Substituents
  • Pyrene
  • Phenanthrol
  • Phenanthrene
  • Naphthalene
  • Secondary alcohol
  • 1,2-diol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular Framework Aromatic homopolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00137 mg/mLALOGPS
logP3.61ALOGPS
logP3.31ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)13.15ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity88.04 m3·mol-1ChemAxon
Polarizability31.45 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
Benzo[a]pyrene-7,8-diol + Glutathione <> 7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene + Water
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-e746f506858cf64c915aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9i-1090000000-fcf1f10a896618157892View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-1290000000-d88f3784dd0a513870f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-7c6172f7110a47ae0a1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-40d4296cbb4974e7d7c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a70-1090000000-35194879c01560da4ee1View in MoNA
References
References:
  • Chary, P., Latham, G. J., Robberson, D. L., Kim, S. J., Han, S., Harris, C. M., Harris, T. M., Lloyd, R. S. (1995). "In vivo and in vitro replication consequences of stereoisomeric benzo[a]pyrene-7,8-dihydrodiol 9,10-epoxide adducts on adenine N6 at the second position of N-ras codon 61." J Biol Chem 270:4990-5000. Pubmed: 7890605
  • 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
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB60438
Pubchem Compound ID25892
Kegg IDC14852
ChemSpider ID24123
Wikipedia IDNot Available
BioCyc IDE-37-DIMETHYLOCTA-16-DIEN-38-DIOL
EcoCyc IDE-37-DIMETHYLOCTA-16-DIEN-38-DIOL

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