2.0 2012-05-31 14:28:26 -0600 2015-06-03 17:19:21 -0600 ECMDB20118 M2MDB000966 Benzo[a]pyrene-4,5-oxide 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) (+)-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-(3a&alpha;,4&beta;,5&alpha;,6a&alpha;))- 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-(3a&alpha;,4&beta;,5&alpha;,6a&alpha;))- 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 C20H12O 268.3087 268.088815006 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 benzo(a)pyrene 4,5-oxide 37574-47-3 O1C2C1C1=CC3=CC=CC=C3C3=C1C1=C(C=CC=C21)C=C3 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 XGZQLNASOQVQTD-UHFFFAOYSA-N Inner membrane Membrane Outer membrane logp 5.24 ALOGPS logs -7.23 ALOGPS solubility 1.57e-05 g/l ALOGPS logp 4.52 ChemAxon pka_strongest_basic -4.3 ChemAxon iupac 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 ChemAxon average_mass 268.3087 ChemAxon mono_mass 268.088815006 ChemAxon smiles O1C2C1C1=CC3=CC=CC=C3C3=C1C1=C(C=CC=C21)C=C3 ChemAxon formula C20H12O ChemAxon 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 ChemAxon inchikey XGZQLNASOQVQTD-UHFFFAOYSA-N ChemAxon polar_surface_area 12.53 ChemAxon refractivity 82.9 ChemAxon polarizability 29.84 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon glutathione metabolism III The biosynthesis of glutathione starts with the introduction of L-glutamic acid through either a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a glutamate / aspartate ABC transporter. Once in the cytoplasm, L-glutamice acid reacts with L-cysteine through an ATP glutamate-cysteine ligase resulting in gamma-glutamylcysteine. This compound reacts which Glycine through an ATP driven glutathione synthetase thus catabolizing Glutathione. This compound is metabolized through a spontaneous reaction with an oxidized glutaredoxin resulting in a reduced glutaredoxin and an oxidized glutathione. This compound is reduced by a NADPH glutathione reductase resulting in a glutathione. PW002018 Metabolic Specdb::CMs 36222 Specdb::CMs 175296 Specdb::NmrOneD 272558 Specdb::NmrOneD 272559 Specdb::NmrOneD 272560 Specdb::NmrOneD 272561 Specdb::NmrOneD 272562 Specdb::NmrOneD 272563 Specdb::NmrOneD 272564 Specdb::NmrOneD 272565 Specdb::NmrOneD 272566 Specdb::NmrOneD 272567 Specdb::NmrOneD 272568 Specdb::NmrOneD 272569 Specdb::NmrOneD 272570 Specdb::NmrOneD 272571 Specdb::NmrOneD 272572 Specdb::NmrOneD 272573 Specdb::NmrOneD 272574 Specdb::NmrOneD 272575 Specdb::NmrOneD 272576 Specdb::NmrOneD 272577 Specdb::MsMs 27677 Specdb::MsMs 27678 Specdb::MsMs 27679 Specdb::MsMs 34235 Specdb::MsMs 34236 Specdb::MsMs 34237 37786 34648 C14851 CPD-722 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 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. 18312271 Glutathione S-transferase P0A9D2 GST_ECOLI gst http://ecmdb.ca/proteins/P0A9D2.xml Biotin sulfoxide reductase P20099 BISC_ECOLI bisC http://ecmdb.ca/proteins/P20099.xml GSH-dependent disulfide bond oxidoreductase P77526 yfcG http://ecmdb.ca/proteins/P77526.xml Benzo[a]pyrene-4,5-oxide + Glutathione <> 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene R07083 Benzo[a]pyrene-4,5-oxide + Red-Thioredoxin Biotin + Water + Ox-Thioredoxin RXN0-6277