2.0 2012-05-31 14:27:15 -0600 2015-06-03 17:19:18 -0600 ECMDB20096 M2MDB000944 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene 4,5-dihydro-4-hydroxy-5-s-glutathionyl-benzo[a]pyrene is a member of the chemical class known as Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. 3-amino-2-propanol is invovled in L-threonine metabolism. D-1-Amino-2-propanol:NAD+ oxidoreductase activity, which catalyzes the second step in a pathway wherein L-threonine is converted to D-1-amino-2-propanol via the intermediate formation of aminoacetone, has been purified 500-fold from Escherichia coli K-12. (PMID 359547) (R)-1-aminopropan-2-ol 1-Amino-2-propanol 3-Amino-2-propanol Aminopropanol D-1-Amino-2-propanol D-1-Aminopropan-2-ol DL-1-amino-2-propanol C30H29N3O7S 575.632 575.172620987 (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-({11-hydroxypentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1(19),2,4,6,8,12,14,16(20),17-nonaen-10-yl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}butanoic acid (2S)-2-amino-4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-({11-hydroxypentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1(19),2,4,6,8,12,14,16(20),17-nonaen-10-yl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}butanoic acid [H][C@](N)(CCC(O)=N[C@@]([H])(CSC1([H])C2=CC3=CC=CC=C3C3=C2C2=C(C=CC=C2C1([H])O)C=C3)C(O)=NCC(O)=O)C(O)=O InChI=1S/C30H29N3O7S/c31-21(30(39)40)10-11-23(34)33-22(29(38)32-13-24(35)36)14-41-28-20-12-16-4-1-2-6-17(16)18-9-8-15-5-3-7-19(27(28)37)25(15)26(18)20/h1-9,12,21-22,27-28,37H,10-11,13-14,31H2,(H,32,38)(H,33,34)(H,35,36)(H,39,40)/t21-,22-,27?,28?/m0/s1 PZXCOGFLSNREMF-SUZCJKPRSA-N Outer membrane Inner membrane logp 0.19 ALOGPS logs -5.23 ALOGPS solubility 3.42e-03 g/l ALOGPS logp 0.68 ChemAxon pka_strongest_acidic 2.07 ChemAxon pka_strongest_basic 9.54 ChemAxon iupac (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-({11-hydroxypentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1(19),2,4,6,8,12,14,16(20),17-nonaen-10-yl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}butanoic acid ChemAxon average_mass 575.632 ChemAxon mono_mass 575.172620987 ChemAxon smiles [H][C@](N)(CCC(O)=N[C@@]([H])(CSC1([H])C2=CC3=CC=CC=C3C3=C2C2=C(C=CC=C2C1([H])O)C=C3)C(O)=NCC(O)=O)C(O)=O ChemAxon formula C30H29N3O7S ChemAxon inchi InChI=1S/C30H29N3O7S/c31-21(30(39)40)10-11-23(34)33-22(29(38)32-13-24(35)36)14-41-28-20-12-16-4-1-2-6-17(16)18-9-8-15-5-3-7-19(27(28)37)25(15)26(18)20/h1-9,12,21-22,27-28,37H,10-11,13-14,31H2,(H,32,38)(H,33,34)(H,35,36)(H,39,40)/t21-,22-,27?,28?/m0/s1 ChemAxon inchikey PZXCOGFLSNREMF-SUZCJKPRSA-N ChemAxon polar_surface_area 186.03 ChemAxon refractivity 153.14 ChemAxon polarizability 59.66 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 10 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Collection of Reactions without pathways PW001891 Metabolic 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 34400 Specdb::CMs 48175 Specdb::CMs 282429 Specdb::CMs 374119 Specdb::CMs 374120 Specdb::CMs 374121 Specdb::CMs 374122 Specdb::CMs 374123 Specdb::CMs 374124 Specdb::CMs 374125 Specdb::CMs 374126 Specdb::CMs 374127 Specdb::CMs 374128 Specdb::CMs 374129 Specdb::CMs 374130 Specdb::CMs 374131 Specdb::CMs 374132 Specdb::CMs 374133 Specdb::CMs 374134 Specdb::CMs 374135 Specdb::CMs 374136 Specdb::CMs 374137 Specdb::CMs 374138 Specdb::CMs 374139 Specdb::CMs 374140 Specdb::NmrOneD 259548 Specdb::NmrOneD 259549 Specdb::NmrOneD 259550 Specdb::NmrOneD 259551 Specdb::NmrOneD 259552 Specdb::NmrOneD 259553 Specdb::NmrOneD 259554 Specdb::NmrOneD 259555 Specdb::NmrOneD 259556 Specdb::NmrOneD 259557 Specdb::NmrOneD 259558 Specdb::NmrOneD 259559 Specdb::NmrOneD 259560 Specdb::NmrOneD 259561 Specdb::NmrOneD 259562 Specdb::NmrOneD 259563 Specdb::NmrOneD 259564 Specdb::NmrOneD 259565 Specdb::NmrOneD 259566 Specdb::NmrOneD 259567 Specdb::MsMs 27419 Specdb::MsMs 27420 Specdb::MsMs 27421 Specdb::MsMs 33977 Specdb::MsMs 33978 Specdb::MsMs 33979 11954068 10128363 C14855 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 Campbell, R. L., Swain, R. R., Dekker, E. E. (1978). "Purification, separation, and characterization of two molecular forms of D-1-amino-2-propanol:NAD+ oxidoreductase activity from extracts of Escherichia coli K-12." J Biol Chem 253:7282-7288. 359547 Glutathione S-transferase P0A9D2 GST_ECOLI gst http://ecmdb.ca/proteins/P0A9D2.xml Glycerol dehydrogenase P0A9S5 GLDA_ECOLI gldA http://ecmdb.ca/proteins/P0A9S5.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 1-Amino-2-propanol + NAD + 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene < NADH + Hydrogen ion + Aminoacetone PW_R005365