2.02012-07-30 14:55:12 -06002015-06-03 17:21:04 -0600ECMDB21282M2MDB001688S-Adenosyl-4-methylthio-2-oxobutanoateS-adenosyl-4-methylthio-2-oxobutanoate is a member of the chemical class known as Purine Nucleosides and Analogues. These are compounds comprising a purine base attached to a sugar. (3-carboxy-3-oxopropyl)(5'-deoxyadenosin-5'-yl)(methyl)sulfanium(3-carboxy-3-oxopropyl)(5'-deoxyadenosin-5'-yl)(methyl)sulfonium(3-carboxy-3-oxopropyl)(5'-deoxyadenosin-5'-yl)(methyl)sulphanium(3-carboxy-3-oxopropyl)(5'-deoxyadenosin-5'-yl)(methyl)sulphoniumS-Adenosyl-4-methylthio-2-oxobutanoateS-Adenosyl-4-methylthio-2-oxobutanoic acidSA4MT2OBA{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}(3-carboxy-3-oxopropyl)methylsulfonium{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}(3-carboxy-3-oxopropyl)methylsulphoniumC15H20N5O6S398.414398.113429087{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(3-carboxy-3-oxopropyl)methylsulfanium{[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(3-carboxy-3-oxopropyl)methylsulfaniumC[S+](CCC(=O)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2NInChI=1S/C15H19N5O6S/c1-27(3-2-7(21)15(24)25)4-8-10(22)11(23)14(26-8)20-6-19-9-12(16)17-5-18-13(9)20/h5-6,8,10-11,14,22-23H,2-4H2,1H3,(H2-,16,17,18,24,25)/p+1/t8-,10-,11-,14-,27?/m1/s1UOKVQQMBGVMXPU-CJPDYEHRSA-OCytosollogp-0.25logs-2.65solubility9.77e-01 g/llogp-3.6pka_strongest_acidic2.75pka_strongest_basic4.99iupac{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(3-carboxy-3-oxopropyl)methylsulfaniumaverage_mass398.414mono_mass398.113429087smilesC[S+](CCC(=O)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2NformulaC15H20N5O6SinchiInChI=1S/C15H19N5O6S/c1-27(3-2-7(21)15(24)25)4-8-10(22)11(23)14(26-8)20-6-19-9-12(16)17-5-18-13(9)20/h5-6,8,10-11,14,22-23H,2-4H2,1H3,(H2-,16,17,18,24,25)/p+1/t8-,10-,11-,14-,27?/m1/s1inchikeyUOKVQQMBGVMXPU-CJPDYEHRSA-Opolar_surface_area173.68refractivity93.72polarizability38.63rotatable_bond_count7acceptor_count10donor_count4physiological_charge0formal_charge1Biotin metabolismBiotin (vitamin H or vitamin B7) is the essential cofactor of biotin-dependent carboxylases, such as pyruvate carboxylase and acetyl-CoA carboxylase.In E. coli and many organisms, pimelate thioester is derived from malonyl-ACP. The pathway starts with a malonyl-[acp] interacting with S-adenosylmethionine through a biotin synthesis protein BioC resulting in a S-adenosylhomocysteine and a malonyl-[acp] methyl ester. The latter compound is then involved in the synthesis of a 3-ketoglutaryl-[acp] methyl ester through a 3-oxoacyl-[acyl-carrier-protein] synthase. The compound 3-ketoglutaryl-[acp] methyl ester is reduced by a NADPH mediated 3-oxoacyl-[acyl-carrier-protein] reductase resulting in a 3R-hydroxyglutaryl-[acp] methyl ester. This compound is then dehydrated through ad (3R)-hydroxymyristoyl-[acp] dehydratase producing a enoylglutaryl-[acp] methyl ester. This compound is then reduced through a NADPH mediated enoyl-acp-reductase [NADH] resulting in a glutaryl-[acp] methyl ester. This compound interacts with a malonyl-[acp] through a 3-oxoacyl-[acp] synthase 2 resulting in a 3-ketopimeloyl [acp] methyl ester. This compound is then reduced through a NADPH 3-oxoacyl [acp] reductase producing a 3-hydroxypimeloyl-[acp] methyl ester and then dehydrated by (3R)-hydroxymyristoyl-[acp] dehydratase to produce a enoylpimeloyl-[acp] methyl ester. This compound is then reduced by a NADPH dependent enoyl-[acp]reductase resulting in a pimeloyl-[acp] methyl ester. This compound then reacts with water through a carboxylesterase resulting in a pimeloyl-[acp] and a methanol. The pimeloyl-acp reacts with L-alanine through a 8-amino-7-oxononanoate synthase resulting in 8-amino-7-oxononanoate which in turn reacts with S-adenosylmethionine through a 7,8 diaminonanoate transaminase resulting in a S-adenosyl-4-methylthio-2-oxobutanoate and 7,8 diaminononanoate. The latter compound is then dephosphorylated through a dethiobiotin synthetase resulting in a dethiobiotin. This compound interacts with a sulfurated[sulfur carrier), a hydrogen ion and a S-adenosylmethionine through a biotin synthase to produce Biotin and releasing l-methionine and a 5-deoxyadenosine.
Biotin is then metabolized by a bifunctional protein resulting in pyrophosphate and Biotinyl-5-AMP which in turn reacts with the same protein (bifunctional protein birA resulting ina biotin caroxyl carrying protein.This product then enters the fatty acid biosynthesis.
PW000762ec00780MetabolicMetabolic pathwayseco01100biotin biosynthesis from 7-keto-8-aminopelargonatePWY0-1507Specdb::NmrOneD293395Specdb::NmrOneD293396Specdb::NmrOneD293397Specdb::NmrOneD293398Specdb::NmrOneD293399Specdb::NmrOneD293400Specdb::NmrOneD293401Specdb::NmrOneD293402Specdb::NmrOneD293403Specdb::NmrOneD293404Specdb::NmrOneD293405Specdb::NmrOneD293406Specdb::NmrOneD293407Specdb::NmrOneD293408Specdb::NmrOneD293409Specdb::NmrOneD293410Specdb::NmrOneD293411Specdb::NmrOneD293412Specdb::NmrOneD293413Specdb::NmrOneD293414Specdb::MsMs1320817Specdb::MsMs1320818Specdb::MsMs1320819440336389303C044258944S-ADENOSYL-4-METHYLTHIO-2-OXOBUTANOATEKeseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.17765195Adenosylmethionine-8-amino-7-oxononanoate aminotransferaseP12995BIOA_ECOLIbioAhttp://ecmdb.ca/proteins/P12995.xml8-Amino-7-oxononanoate + S-Adenosylmethionine <> S-Adenosyl-4-methylthio-2-oxobutanoate + 7,8-DiaminononanoateR03231DAPASYN-RXNS-Adenosylmethionine + 8-Amino-7-oxononanoate > S-Adenosyl-4-methylthio-2-oxobutanoate + 7,8-DiaminononanoateDAPASYN-RXNS-adenosyl-L-methionine + 8-Amino-7-oxononanoate > S-Adenosyl-4-methylthio-2-oxobutanoate + 7,8-Diaminononanoate8 8-Amino-7-oxononanoate + S-Adenosylmethionine <> S-Adenosyl-4-methylthio-2-oxobutanoate +7 7,8-Diaminononanoate8 8-Amino-7-oxononanoate + S-Adenosylmethionine <> S-Adenosyl-4-methylthio-2-oxobutanoate +7 7,8-Diaminononanoate