2.0 2012-05-31 14:28:29 -0600 2015-06-03 17:19:21 -0600 ECMDB20119 M2MDB000967 Benzo[a]pyrene-7,8-diol 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) (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 C20H14O2 286.324 286.099379692 pentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1,3,7,9(19),10,12(20),13,15,17-nonaene-5,6-diol benzo(a)pyrene 7,8-diol 13345-25-0 OC1C=CC2=C3C=CC4=CC=CC5=C4C3=C(C=C5)C=C2C1O 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 YDXRLMMGARHIIC-UHFFFAOYSA-N Inner membrane Membrane Outer membrane logp 3.61 ALOGPS logs -5.32 ALOGPS solubility 1.37e-03 g/l ALOGPS logp 3.31 ChemAxon pka_strongest_acidic 13.15 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac pentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1,3,7,9(19),10,12(20),13,15,17-nonaene-5,6-diol ChemAxon average_mass 286.324 ChemAxon mono_mass 286.099379692 ChemAxon smiles OC1C=CC2=C3C=CC4=CC=CC5=C4C3=C(C=C5)C=C2C1O ChemAxon formula C20H14O2 ChemAxon 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 ChemAxon inchikey YDXRLMMGARHIIC-UHFFFAOYSA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 88.04 ChemAxon polarizability 31.45 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 36032 Specdb::CMs 48211 Specdb::CMs 119869 Specdb::CMs 135190 Specdb::CMs 142924 Specdb::CMs 859918 Specdb::CMs 859919 Specdb::CMs 859920 Specdb::CMs 859921 Specdb::CMs 859922 Specdb::NmrOneD 338588 Specdb::NmrOneD 338589 Specdb::NmrOneD 338590 Specdb::NmrOneD 338591 Specdb::NmrOneD 338592 Specdb::NmrOneD 338593 Specdb::NmrOneD 338594 Specdb::NmrOneD 338595 Specdb::NmrOneD 338596 Specdb::NmrOneD 338597 Specdb::NmrOneD 338598 Specdb::NmrOneD 338599 Specdb::NmrOneD 338600 Specdb::NmrOneD 338601 Specdb::NmrOneD 338602 Specdb::NmrOneD 338603 Specdb::NmrOneD 338604 Specdb::NmrOneD 338605 Specdb::NmrOneD 338606 Specdb::NmrOneD 338607 Specdb::MsMs 26255 Specdb::MsMs 26256 Specdb::MsMs 26257 Specdb::MsMs 32813 Specdb::MsMs 32814 Specdb::MsMs 32815 25892 24123 C14852 E-37-DIMETHYLOCTA-16-DIEN-38-DIOL 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. 22080510 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. 7890605 Glutathione S-transferase P0A9D2 GST_ECOLI gst http://ecmdb.ca/proteins/P0A9D2.xml GSH-dependent disulfide bond oxidoreductase P77526 yfcG http://ecmdb.ca/proteins/P77526.xml Benzo[a]pyrene-7,8-diol + Glutathione <> 7,8-Dihydro-7-hydroxy-8-S-glutathionyl-benzo[a]pyrene + Water R07084