2.02012-05-31 14:28:29 -06002015-06-03 17:19:21 -0600ECMDB20119M2MDB000967Benzo[a]pyrene-7,8-diolBenzo[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)(E)-3,7-dimethylocta-1,6-dien-3,8-diol(E)-Benzo(a)pyrene-7,8-dihydrodiol7,8-Dihydro 7,8-dihydroxybenzo(a)pyrene7,8-Dihydro-7,8-dihydroxy-(E)-Benzo(a)pyrene7,8-Dihydro-7,8-dihydroxy-Benzo(a)pyrene7,8-Dihydro-7,8-dihydroxybenzopyrene7,8-Dihydrobenzo(a)pyrene-7,8-diol7,8-Dihydroxy-7,8-dihydrobenzo(a)pyrene7,8-Diol-benzo(a)pyreneBenzo(a)pyrene 7,8-dihydrodiolBenzo(a)pyrene 7,8-dihydrodiol, (7R-trans)-isomerBenzo(a)pyrene 7,8-dihydrodiol, (7S-trans)-isomerBenzo(a)pyrene 7,8-dihydrodiol, (cis)-isomerBenzo(a)pyrene 7,8-dihydrodiol, (trans)-(+-)-isomerBenzo(a)pyrene 7,8-dihydrodiol, (trans)-isomerBenzo(a)pyrene 7,8-diolBenzo(a)pyrene-7,8-dihydrodiolBenzo(a)pyrene-7,8-diolBenzopyrene-7,8-dihydrodiolBenzo[a]pyrene-7,8-dihydrodiolBP-7,8 diolBP-7,8-dihydrodiolCis-7,8-Dihydrobenzo[a]pyrendiolTrans-7,8-Dihydroxy-7,8-dihydrobenzo(a)pyreneTrans-Benzopyrene 7,8-dihydrodiolC20H14O2286.324286.099379692pentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1,3,7,9(19),10,12(20),13,15,17-nonaene-5,6-diolbenzo(a)pyrene 7,8-diol13345-25-0OC1C=CC2=C3C=CC4=CC=CC5=C4C3=C(C=C5)C=C2C1OInChI=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/h1-10,17,20-22HYDXRLMMGARHIIC-UHFFFAOYSA-NInner membraneMembraneOuter membranelogp3.61logs-5.32solubility1.37e-03 g/llogp3.31pka_strongest_acidic13.15pka_strongest_basic-3.4iupacpentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1,3,7,9(19),10,12(20),13,15,17-nonaene-5,6-diolaverage_mass286.324mono_mass286.099379692smilesOC1C=CC2=C3C=CC4=CC=CC5=C4C3=C(C=C5)C=C2C1OformulaC20H14O2inchiInChI=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/h1-10,17,20-22HinchikeyYDXRLMMGARHIIC-UHFFFAOYSA-Npolar_surface_area40.46refractivity88.04polarizability31.45rotatable_bond_count0acceptor_count2donor_count2physiological_charge0formal_charge0Specdb::CMs36032Specdb::CMs48211Specdb::CMs119869Specdb::CMs135190Specdb::CMs142924Specdb::CMs859918Specdb::CMs859919Specdb::CMs859920Specdb::CMs859921Specdb::CMs859922Specdb::NmrOneD338588Specdb::NmrOneD338589Specdb::NmrOneD338590Specdb::NmrOneD338591Specdb::NmrOneD338592Specdb::NmrOneD338593Specdb::NmrOneD338594Specdb::NmrOneD338595Specdb::NmrOneD338596Specdb::NmrOneD338597Specdb::NmrOneD338598Specdb::NmrOneD338599Specdb::NmrOneD338600Specdb::NmrOneD338601Specdb::NmrOneD338602Specdb::NmrOneD338603Specdb::NmrOneD338604Specdb::NmrOneD338605Specdb::NmrOneD338606Specdb::NmrOneD338607Specdb::MsMs26255Specdb::MsMs26256Specdb::MsMs26257Specdb::MsMs32813Specdb::MsMs32814Specdb::MsMs328152589224123C14852E-37-DIMETHYLOCTA-16-DIEN-38-DIOLKanehisa, 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-D114.22080510Chary, 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 270:4990-5000.7890605Glutathione S-transferaseP0A9D2GST_ECOLIgsthttp://ecmdb.ca/proteins/P0A9D2.xmlGSH-dependent disulfide bond oxidoreductaseP77526yfcGhttp://ecmdb.ca/proteins/P77526.xmlBenzo[a]pyrene-7,8-diol + Glutathione <> 7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene + WaterR07084