2.02012-05-31 14:21:05 -06002015-06-03 17:19:03 -0600ECMDB12208M2MDB000829D-Erythro-imidazole-glycerol-phosphateD-Erythro-imidazole-glycerol-phosphate is an intermediate in Histidine metabolism. It is a substrate for imidazoleglycerol-phosphate dehydratase (hisB) and can be generated from Phosphoribulosyl-formimino-AICAR-phosphate then it is converted to Imidazole-acetol phosphate.D-Erythro-1-(imidazol-4-yl)-glycerol-3-phosphateD-erythro-1-(Imidazol-4-yl)-glycerol-3-phosphoric acidD-Erythro-1-(Imidazol-4-yl)glycerol 3-phosphateD-erythro-1-(Imidazol-4-yl)glycerol 3-phosphoric acidD-Erythro-Imidazole-glycerol 3-phosphateD-erythro-Imidazole-glycerol 3-phosphoric acidD-Erythro-imidazole-glycerol phosphateD-erythro-Imidazole-glycerol phosphoric acidD-erythro-imidazole-glycerol-PD-erythro-Imidazole-glycerol-phosphoric acidD-Erythro-imidazoleglycerol-phosphateD-erythro-Imidazoleglycerol-phosphoric acidEIGPErythro-imidazole-glycerol-PErythro-imidazole-glycerol-phosphateerythro-Imidazole-glycerol-phosphoric acidIGPImidazole glycerol phosphateImidazole glycerol phosphoric acidC6H11N2O6P238.1351238.035472606[(2R,3S)-2,3-dihydroxy-3-(1H-imidazol-4-yl)propoxy]phosphonic acid(2R,3S)-2,3-dihydroxy-3-(1H-imidazol-4-yl)propoxyphosphonic acid36244-87-8O[C@H](COP(O)(O)=O)[C@@H](O)C1=CNC=N1InChI=1S/C6H11N2O6P/c9-5(2-14-15(11,12)13)6(10)4-1-7-3-8-4/h1,3,5-6,9-10H,2H2,(H,7,8)(H2,11,12,13)/t5-,6+/m1/s1HFYBTHCYPKEDQQ-RITPCOANSA-NSolidCytosollogp-1.59logs-1.03solubility2.22e+01 g/llogp-4.3pka_strongest_acidic1.48pka_strongest_basic5.79iupac[(2R,3S)-2,3-dihydroxy-3-(1H-imidazol-4-yl)propoxy]phosphonic acidaverage_mass238.1351mono_mass238.035472606smilesO[C@H](COP(O)(O)=O)[C@@H](O)C1=CNC=N1formulaC6H11N2O6PinchiInChI=1S/C6H11N2O6P/c9-5(2-14-15(11,12)13)6(10)4-1-7-3-8-4/h1,3,5-6,9-10H,2H2,(H,7,8)(H2,11,12,13)/t5-,6+/m1/s1inchikeyHFYBTHCYPKEDQQ-RITPCOANSA-Npolar_surface_area135.9refractivity48.18polarizability19.79rotatable_bond_count5acceptor_count6donor_count5physiological_charge-2formal_charge0Histidine metabolismec00340Secondary Metabolites: Histidine biosynthesisHistidine 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.PW000984Metabolichistidine biosynthesisHistidine 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.PW000810Metabolichistidine biosynthesisHISTSYN-PWYSpecdb::CMs3138Specdb::CMs39863Specdb::CMs130598Specdb::CMs138332Specdb::NmrOneD11542Specdb::NmrOneD11543Specdb::NmrOneD11544Specdb::NmrOneD11545Specdb::NmrOneD11546Specdb::NmrOneD11547Specdb::NmrOneD11548Specdb::NmrOneD11549Specdb::NmrOneD11550Specdb::NmrOneD11551Specdb::NmrOneD11552Specdb::NmrOneD11553Specdb::NmrOneD11554Specdb::NmrOneD11555Specdb::NmrOneD11556Specdb::NmrOneD11557Specdb::NmrOneD11558Specdb::NmrOneD11559Specdb::NmrOneD11560Specdb::NmrOneD11561Specdb::MsMs27866Specdb::MsMs27867Specdb::MsMs27868Specdb::MsMs34424Specdb::MsMs34425Specdb::MsMs34426Specdb::MsMs2738857Specdb::MsMs2738858Specdb::MsMs2738859Specdb::MsMs2969573Specdb::MsMs2969574Specdb::MsMs2969575HMDB12208440431389372C04666D-ERYTHRO-IMIDAZOLE-GLYCEROL-PKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510van 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 370:17-25.17765195Histidine biosynthesis bifunctional protein hisBP06987HIS7_ECOLIhisBhttp://ecmdb.ca/proteins/P06987.xmlImidazole glycerol phosphate synthase subunit hisHP60595HIS5_ECOLIhisHhttp://ecmdb.ca/proteins/P60595.xmlImidazole glycerol phosphate synthase subunit hisFP60664HIS6_ECOLIhisFhttp://ecmdb.ca/proteins/P60664.xmlL-Glutamine + Phosphoribulosylformimino-AICAR-P > Phosphoribosyl formamidocarboxamide + D-Erythro-imidazole-glycerol-phosphate + L-Glutamate + Hydrogen ionD-Erythro-imidazole-glycerol-phosphate <> Water + Imidazole acetol-phosphateR03457IMIDPHOSDEHYD-RXNPhosphoribulosylformimino-AICAR-P + L-Glutamine <> D-Erythro-imidazole-glycerol-phosphate + AICAR + L-GlutamateR04558GLUTAMIDOTRANS-RXNPhosphoribulosylformimino-AICAR-P + L-Glutamine > Hydrogen ion + L-Glutamate + D-Erythro-imidazole-glycerol-phosphate + AICARGLUTAMIDOTRANS-RXND-Erythro-imidazole-glycerol-phosphate > Imidazole acetol-phosphate + WaterIMIDPHOSDEHYD-RXNPhosphoribulosylformimino-AICAR-P + L-Glutamine > L-Glutamic acid + Hydrogen ion + 5-Amino-4-imidazolecarboxyamide + D-Erythro-imidazole-glycerol-phosphate + L-GlutamatePW_R002869