2.0 2012-05-31 14:21:11 -0600 2015-06-03 17:19:03 -0600 ECMDB12236 M2MDB000831 Imidazole acetol-phosphate Imidazole acetol-phosphate is involved in the histidine biosynthesis pathway. Imidazole acetol-phosphate is created by the breakdown of D-erythro-imidazole-glycerol-phosphate into imidazole acetol-phosphate and H2O. Imidazoleglycerol-phosphate dehydratase catalyzes this reaction. 1-(1H-Imidazol-4-yl)-3-(phosphonooxy)-2-propanone 3-(1H-Imidazol-4-yl)-2-oxopropyl dihydrogen phosphate 3-(1H-Imidazol-4-yl)-2-oxopropyl dihydrogen phosphoric acid 3-(Imidazol-4-yl)-2-oxopropyl dihydrogen phosphate 3-(Imidazol-4-yl)-2-oxopropyl dihydrogen phosphoric acid 3-(Imidazol-4-yl)-2-oxopropyl phosphate 3-(Imidazol-4-yl)-2-oxopropyl phosphoric acid IAP Imidazole acetol phosphate Imidazole acetol phosphoric acid Imidazole acetol-p Imidazole acetol-phosphoric acid Imidazole-acetol phosphate Imidazole-acetol phosphoric acid C6H9N2O5P 220.1198 220.02490792 [3-(1H-imidazol-4-yl)-2-oxopropoxy]phosphonic acid 3-(1H-imidazol-4-yl)-2-oxopropoxyphosphonic acid 99979-59-6 OP(O)(=O)OCC(=O)CC1=CNC=N1 InChI=1S/C6H9N2O5P/c9-6(3-13-14(10,11)12)1-5-2-7-4-8-5/h2,4H,1,3H2,(H,7,8)(H2,10,11,12) YCFFMSOLUMRAMD-UHFFFAOYSA-N Solid Cytosol logp -0.90 ALOGPS logs -1.17 ALOGPS solubility 1.49e+01 g/l ALOGPS logp -3 ChemAxon pka_strongest_acidic 1.23 ChemAxon pka_strongest_basic 6.65 ChemAxon iupac [3-(1H-imidazol-4-yl)-2-oxopropoxy]phosphonic acid ChemAxon average_mass 220.1198 ChemAxon mono_mass 220.02490792 ChemAxon smiles OP(O)(=O)OCC(=O)CC1=CNC=N1 ChemAxon formula C6H9N2O5P ChemAxon inchi InChI=1S/C6H9N2O5P/c9-6(3-13-14(10,11)12)1-5-2-7-4-8-5/h2,4H,1,3H2,(H,7,8)(H2,10,11,12) ChemAxon inchikey YCFFMSOLUMRAMD-UHFFFAOYSA-N ChemAxon polar_surface_area 112.51 ChemAxon refractivity 46.07 ChemAxon polarizability 18.15 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Tyrosine metabolism ec00350 Phenylalanine metabolism The pathways of the metabolism of phenylalaline begins with the conversion of chorismate to prephenate through a P-protein (chorismate mutase:pheA). Prephenate then interacts with a hydrogen ion through the same previous enzyme resulting in a release of carbon dioxide, water and a phenolpyruvic acid. Three enzymes those enconde by tyrB, aspC and ilvE are involved in catalyzing the third step of these pathways, all three can contribute to the synthesis of phenylalanine: only tyrB and aspC contribute to biosynthesis of tyrosine. Phenolpyruvic acid can also be obtained from a reversivle reaction with ammonia, a reduced acceptor and a D-amino acid dehydrogenase, resulting in a water, an acceptor and a D-phenylalanine, which can be then transported into the periplasmic space by aromatic amino acid exporter. L-phenylalanine also interacts in two reversible reactions, one involved with oxygen through a catalase peroxidase resulting in a carbon dioxide and 2-phenylacetamide. The other reaction involved an interaction with oxygen through a phenylalanine aminotransferase resulting in a oxoglutaric acid and phenylpyruvic acid. L-phenylalanine can be imported into the cytoplasm through an aromatic amino acid:H+ symporter AroP. The compound can also be imported into the periplasmic space through a transporter: L-amino acid efflux transporter. PW000921 ec00360 Metabolic Phenylalanine, tyrosine and tryptophan biosynthesis ec00400 Novobiocin biosynthesis ec00401 Tropane, piperidine and pyridine alkaloid biosynthesis ec00960 Histidine metabolism ec00340 Metabolic pathways eco01100 Secondary Metabolites: Histidine biosynthesis Histidine biosynthesis starts with a product of PRPP biosynthesis pathway, phosphoribosyl pyrophosphate which interacts with a hydrogen ion through an ATP phosphoribosyltransferase resulting in an pyrophosphate and a phosphoribosyl-ATP. This compound interacts with water through a phosphoribosyl-AMP cyclohydrolase / phosphoribosyl-ATP pyrophosphatase resulting in the release of pyrophosphate, hydrogen ion and a phosphoribosyl-AMP. This enzyme proceeds to interact with phosphoribosyl-AMP and water resulting in a 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide. This compound is then isomerized by a N-(5'-phospho-L-ribosyl-formimino)-5-amino-1-(5'-phosphoribosyl)-4-imidazolecarboxamide isomerase resulting in a PhosphoribosylformiminoAICAR-phosphate. This compound reacts with L-glutamine through an imidazole glycerol phosphate synthase resulting in a L-glutamic acid, hydrogen ion, 5-aminoimidazole-4-carboxamide and a D-erythro-imidazole-glycerol-phosphate. This compound reacts with a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase, dehydrating the compound and resulting in a imidazole acetol-phosphate. This compound interacts with L-glutamic acid through a histidinol-phosphate aminotransferase, releasing oxoglutaric acid and L-histidinol-phosphate. The latter compound interacts with water and a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase resulting in L-histidinol and phosphate. L-histidinol interacts with a NAD-driven histidinol dehydrogenase resulting in a Histidinal. This in turn reacts with water in a NAD driven histidinal dehydrogenase resulting in L-Histidine. L-Histidine then represses ATP phosphoribosyltransferase, regulation its own biosynthesis. PW000984 Metabolic histidine biosynthesis Histidine biosynthesis starts with a product of PRPP biosynthesis pathway, phosphoribosyl pyrophosphate which interacts with a hydrogen ion through an ATP phosphoribosyltransferase resulting in an pyrophosphate and a phosphoribosyl-ATP. This compound interacts with water through a phosphoribosyl-AMP cyclohydrolase / phosphoribosyl-ATP pyrophosphatase resulting in the release of pyrophosphate, hydrogen ion and a phosphoribosyl-AMP. This enzyme proceeds to interact with phosphoribosyl-AMP and water resulting in a 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide. This compound is then isomerized by a N-(5'-phospho-L-ribosyl-formimino)-5-amino-1-(5'-phosphoribosyl)-4-imidazolecarboxamide isomerase resulting in a PhosphoribosylformiminoAICAR-phosphate. This compound reacts with L-glutamine through an imidazole glycerol phosphate synthase resulting in a L-glutamic acid, hydrogen ion, 5-aminoimidazole-4-carboxamide and a D-erythro-imidazole-glycerol-phosphate. This compound reacts with a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase, dehydrating the compound and resulting in a imidazole acetol-phosphate. This compound interacts with L-glutamic acid through a histidinol-phosphate aminotransferase, releasing oxoglutaric acid and L-histidinol-phosphate. The latter compound interacts with water and a imidazoleglycerol-phosphate dehydratase / histidinol-phosphatase resulting in L-histidinol and phosphate. L-histidinol interacts with a NAD-driven histidinol dehydrogenase resulting in a Histidinal. This in turn reacts with water in a NAD driven histidinal dehydrogenase resulting in L-Histidine. L-Histidine then represses ATP phosphoribosyltransferase, regulation its own biosynthesis. PW000810 Metabolic histidine biosynthesis HISTSYN-PWY Specdb::CMs 2593 Specdb::CMs 167406 Specdb::NmrOneD 151570 Specdb::NmrOneD 151571 Specdb::NmrOneD 151572 Specdb::NmrOneD 151573 Specdb::NmrOneD 151574 Specdb::NmrOneD 151575 Specdb::NmrOneD 151576 Specdb::NmrOneD 151577 Specdb::NmrOneD 151578 Specdb::NmrOneD 151579 Specdb::NmrOneD 151580 Specdb::NmrOneD 151581 Specdb::NmrOneD 151582 Specdb::NmrOneD 151583 Specdb::NmrOneD 151584 Specdb::NmrOneD 151585 Specdb::NmrOneD 151586 Specdb::NmrOneD 151587 Specdb::NmrOneD 151588 Specdb::NmrOneD 151589 Specdb::MsMs 24809 Specdb::MsMs 24810 Specdb::MsMs 24811 Specdb::MsMs 31367 Specdb::MsMs 31368 Specdb::MsMs 31369 Specdb::MsMs 2344016 Specdb::MsMs 2344017 Specdb::MsMs 2344018 Specdb::MsMs 2595454 Specdb::MsMs 2595455 Specdb::MsMs 2595456 HMDB12236 792 770 C01267 IMIDAZOLE-ACETOL-P 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 AMES BN, HORECKER BL: The biosynthesis of histidine: imidazoleacetol phosphate transaminase. J Biol Chem. 1956 May;220(1):113-28. 13319331 Albritton WL, Levin AP: Some comparative kinetic data on the enzyme imidazoleacetol phosphate:L-glutamate aminotransferase derived from mutant strains of Salmonella typhimurium. J Biol Chem. 1970 May 25;245(10):2525-8. 5445798 AMES BN, MITCHELL HK: The biosynthesis of histidine; imidazoleglycerol phosphate, imidazoleacetol phosphate, and histidinol phosphate. J Biol Chem. 1955 Feb;212(2):687-96. 14353870 LEVIN AP, HARTMAN PE: ACTION OF A HISTIDINE ANALOGUE, 1,2,4-TRIAZOLE-3-ALANINE, IN SALMONELLA TYPHIMURIUM. J Bacteriol. 1963 Oct;86:820-8. 14066480 Henderson GB, Snell EE: Vitamin B 6 -responsive histidine deficiency in mutants of Salmonella typhimurium. Proc Natl Acad Sci U S A. 1971 Dec;68(12):2903-7. 4943547 Histidinol-phosphate aminotransferase P06986 HIS8_ECOLI hisC http://ecmdb.ca/proteins/P06986.xml Histidine biosynthesis bifunctional protein hisB P06987 HIS7_ECOLI hisB http://ecmdb.ca/proteins/P06987.xml L-Glutamate + Imidazole acetol-phosphate <> alpha-Ketoglutarate + Histidinol phosphate R03243 D-Erythro-imidazole-glycerol-phosphate <> Water + Imidazole acetol-phosphate R03457 IMIDPHOSDEHYD-RXN Histidinol phosphate + alpha-Ketoglutarate <> Imidazole acetol-phosphate + L-Glutamate R03243 Imidazole acetol-phosphate + L-Glutamate <> Histidinol phosphate + Oxoglutaric acid HISTAMINOTRANS-RXN D-Erythro-imidazole-glycerol-phosphate > Imidazole acetol-phosphate + Water IMIDPHOSDEHYD-RXN Histidinol phosphate + Oxoglutaric acid > Imidazole acetol-phosphate + L-Glutamate HISTAMINOTRANS-RXN Imidazole acetol-phosphate + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + L-histidinol-phosphate PW_R002871