2.0 2012-05-31 14:28:04 -0600 2015-06-03 17:19:20 -0600 ECMDB20111 M2MDB000959 8-Amino-7-oxononanoate 8-amino-7-oxononanoate is a member of the chemical class known as Medium-chain Keto Acids and Derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. 8-amino-8-oxononanoic is involved in biotin biosynthesis. Diaminopelargonic acid aminotransferase (DAPA AT), which is involved in biotin biosynthesis, catalyzes the transamination of 8-amino-7-oxononanoic acid (KAPA) using S-adenosyl-L-methionine (AdoMet) as amino donor. (PMID 16984394) (8S)-8-amino-7-oxononanoate (8S)-8-amino-7-oxononanoic acid 7-KAP 7-Keto-8-aminopelargonate 7-Keto-8-aminopelargonic acid 7-Oxo-8-amino-nonanoate 7-Oxo-8-amino-nonanoic acid 8-amino-7-oxononanoate 8-Amino-7-oxononanoic acid 8A7ONA KAP KAPA C9H17NO3 187.2362 187.120843415 4707-58-8 CC(N)C(=O)CCCCCC(O)=O InChI=1S/C9H17NO3/c1-7(10)8(11)5-3-2-4-6-9(12)13/h7H,2-6,10H2,1H3,(H,12,13) GUAHPAJOXVYFON-UHFFFAOYSA-N Cytosol logp -1.53 ALOGPS logs 1.18 ALOGPS solubility 9.50e+02 g/l ALOGPS average_mass 187.2362 ChemAxon mono_mass 187.120843415 ChemAxon smiles CC(N)C(=O)CCCCCC(O)=O ChemAxon formula C9H17NO3 ChemAxon inchi InChI=1S/C9H17NO3/c1-7(10)8(11)5-3-2-4-6-9(12)13/h7H,2-6,10H2,1H3,(H,12,13) ChemAxon inchikey GUAHPAJOXVYFON-UHFFFAOYSA-N ChemAxon formal_charge 0 ChemAxon Biotin metabolism Biotin (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. PW000762 ec00780 Metabolic Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 biotin biosynthesis from 7-keto-8-aminopelargonate PWY0-1507 7-keto-8-aminopelargonate biosynthesis I PWY-6519 Specdb::CMs 3294 Specdb::CMs 28207 Specdb::CMs 28439 Specdb::CMs 29341 Specdb::CMs 42796 Specdb::CMs 101902 Specdb::CMs 101903 Specdb::CMs 101904 Specdb::CMs 135827 Specdb::CMs 143561 Specdb::EiMs 593 Specdb::NmrOneD 2105 Specdb::NmrOneD 2799 Specdb::NmrOneD 23002 Specdb::NmrOneD 23003 Specdb::NmrOneD 23004 Specdb::NmrOneD 23005 Specdb::NmrOneD 23006 Specdb::NmrOneD 23007 Specdb::NmrOneD 23008 Specdb::NmrOneD 23009 Specdb::NmrOneD 23010 Specdb::NmrOneD 23011 Specdb::NmrOneD 23012 Specdb::NmrOneD 23013 Specdb::NmrOneD 23014 Specdb::NmrOneD 23015 Specdb::NmrOneD 23016 Specdb::NmrOneD 23017 Specdb::NmrOneD 23018 Specdb::NmrOneD 23019 Specdb::NmrOneD 23020 Specdb::NmrOneD 23021 Specdb::MsMs 25049 Specdb::MsMs 25050 Specdb::MsMs 25051 Specdb::MsMs 31607 Specdb::MsMs 31608 Specdb::MsMs 31609 Specdb::MsMs 2751961 Specdb::MsMs 2751962 Specdb::MsMs 2751963 Specdb::MsMs 2930790 Specdb::MsMs 2930791 Specdb::MsMs 2930792 173 168 C01092 12266 8-AMINO-7-OXONONANOATE Keseler, 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. 21097882 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 van 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. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). 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FEBS J 273:4778-4789. 16984394 Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI bioA http://ecmdb.ca/proteins/P12995.xml 8-amino-7-oxononanoate synthase P12998 BIOF_ECOLI bioF http://ecmdb.ca/proteins/P12998.xml 8-Amino-7-oxononanoate + S-Adenosylmethionine <> S-Adenosyl-4-methylthio-2-oxobutanoate + 7,8-Diaminononanoate R03231 DAPASYN-RXN L-Alanine + Pimeloyl-[acyl-carrier protein] > 8-Amino-7-oxononanoate + acyl carrier protein + Carbon dioxide 6-Carboxyhexanoyl-CoA + L-Alanine + Pimeloyl-[acyl-carrier protein] <> 8-Amino-7-oxononanoate + Coenzyme A + Carbon dioxide + Acyl-carrier protein R03210 Hydrogen ion + L-Alanine + pimeloyl-CoA > Carbon dioxide + Coenzyme A + 8-Amino-7-oxononanoate 7KAPSYN-RXN S-Adenosylmethionine + 8-Amino-7-oxononanoate > S-Adenosyl-4-methylthio-2-oxobutanoate + 7,8-Diaminononanoate DAPASYN-RXN L-Alanine + Hydrogen ion + Pimeloyl-ACPs > 8-Amino-7-oxononanoate + Carbon dioxide + ACP RXN-11484 S-adenosyl-L-methionine + 8-Amino-7-oxononanoate > S-Adenosyl-4-methylthio-2-oxobutanoate + 7,8-Diaminononanoate 6-carboxyhexanoyl-CoA + L-Alanine > 8-Amino-7-oxononanoate + CoA + Carbon dioxide a pimeloyl-[acp] + L-Alanine + L-Alanine > Carbon dioxide + a holo-[acyl-carrier protein] + 8-Amino-7-oxononanoate PW_R002495 a sulfurated [sulfur carrier] + L-Alanine + L-Alanine > 8-Amino-7-oxononanoate + Coenzyme A + Carbon dioxide PW_R002496 8-Amino-7-oxononanoate + S-adenosyl-L-methionine > a sulfurated [sulfur carrier] + 7,8-Diaminononanoate + 7,8-Diaminononanoate PW_R002497 8 8-Amino-7-oxononanoate + S-Adenosylmethionine <> S-Adenosyl-4-methylthio-2-oxobutanoate +7 7,8-Diaminononanoate 6 6-carboxyhexanoyl-CoA + L-Alanine + Pimeloyl-[acyl-carrier protein] <>8 8-Amino-7-oxononanoate + Coenzyme A + Carbon dioxide + Acyl-carrier protein 8 8-Amino-7-oxononanoate + S-Adenosylmethionine <> S-Adenosyl-4-methylthio-2-oxobutanoate +7 7,8-Diaminononanoate