2.0 2012-05-31 14:21:05 -0600 2015-06-03 17:19:03 -0600 ECMDB12208 M2MDB000829 D-Erythro-imidazole-glycerol-phosphate D-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-phosphate D-erythro-1-(Imidazol-4-yl)-glycerol-3-phosphoric acid D-Erythro-1-(Imidazol-4-yl)glycerol 3-phosphate D-erythro-1-(Imidazol-4-yl)glycerol 3-phosphoric acid D-Erythro-Imidazole-glycerol 3-phosphate D-erythro-Imidazole-glycerol 3-phosphoric acid D-Erythro-imidazole-glycerol phosphate D-erythro-Imidazole-glycerol phosphoric acid D-erythro-imidazole-glycerol-P D-erythro-Imidazole-glycerol-phosphoric acid D-Erythro-imidazoleglycerol-phosphate D-erythro-Imidazoleglycerol-phosphoric acid EIGP Erythro-imidazole-glycerol-P Erythro-imidazole-glycerol-phosphate erythro-Imidazole-glycerol-phosphoric acid IGP Imidazole glycerol phosphate Imidazole glycerol phosphoric acid C6H11N2O6P 238.1351 238.035472606 [(2R,3S)-2,3-dihydroxy-3-(1H-imidazol-4-yl)propoxy]phosphonic acid (2R,3S)-2,3-dihydroxy-3-(1H-imidazol-4-yl)propoxyphosphonic acid 36244-87-8 O[C@H](COP(O)(O)=O)[C@@H](O)C1=CNC=N1 InChI=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/s1 HFYBTHCYPKEDQQ-RITPCOANSA-N Solid Cytosol logp -1.59 ALOGPS logs -1.03 ALOGPS solubility 2.22e+01 g/l ALOGPS logp -4.3 ChemAxon pka_strongest_acidic 1.48 ChemAxon pka_strongest_basic 5.79 ChemAxon iupac [(2R,3S)-2,3-dihydroxy-3-(1H-imidazol-4-yl)propoxy]phosphonic acid ChemAxon average_mass 238.1351 ChemAxon mono_mass 238.035472606 ChemAxon smiles O[C@H](COP(O)(O)=O)[C@@H](O)C1=CNC=N1 ChemAxon formula C6H11N2O6P ChemAxon inchi InChI=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/s1 ChemAxon inchikey HFYBTHCYPKEDQQ-RITPCOANSA-N ChemAxon polar_surface_area 135.9 ChemAxon refractivity 48.18 ChemAxon polarizability 19.79 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Histidine metabolism ec00340 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 3138 Specdb::CMs 39863 Specdb::CMs 130598 Specdb::CMs 138332 Specdb::NmrOneD 11542 Specdb::NmrOneD 11543 Specdb::NmrOneD 11544 Specdb::NmrOneD 11545 Specdb::NmrOneD 11546 Specdb::NmrOneD 11547 Specdb::NmrOneD 11548 Specdb::NmrOneD 11549 Specdb::NmrOneD 11550 Specdb::NmrOneD 11551 Specdb::NmrOneD 11552 Specdb::NmrOneD 11553 Specdb::NmrOneD 11554 Specdb::NmrOneD 11555 Specdb::NmrOneD 11556 Specdb::NmrOneD 11557 Specdb::NmrOneD 11558 Specdb::NmrOneD 11559 Specdb::NmrOneD 11560 Specdb::NmrOneD 11561 Specdb::MsMs 27866 Specdb::MsMs 27867 Specdb::MsMs 27868 Specdb::MsMs 34424 Specdb::MsMs 34425 Specdb::MsMs 34426 Specdb::MsMs 2738857 Specdb::MsMs 2738858 Specdb::MsMs 2738859 Specdb::MsMs 2969573 Specdb::MsMs 2969574 Specdb::MsMs 2969575 HMDB12208 440431 389372 C04666 D-ERYTHRO-IMIDAZOLE-GLYCEROL-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 Histidine biosynthesis bifunctional protein hisB P06987 HIS7_ECOLI hisB http://ecmdb.ca/proteins/P06987.xml Imidazole glycerol phosphate synthase subunit hisH P60595 HIS5_ECOLI hisH http://ecmdb.ca/proteins/P60595.xml Imidazole glycerol phosphate synthase subunit hisF P60664 HIS6_ECOLI hisF http://ecmdb.ca/proteins/P60664.xml L-Glutamine + Phosphoribulosylformimino-AICAR-P > Phosphoribosyl formamidocarboxamide + D-Erythro-imidazole-glycerol-phosphate + L-Glutamate + Hydrogen ion D-Erythro-imidazole-glycerol-phosphate <> Water + Imidazole acetol-phosphate R03457 IMIDPHOSDEHYD-RXN Phosphoribulosylformimino-AICAR-P + L-Glutamine <> D-Erythro-imidazole-glycerol-phosphate + AICAR + L-Glutamate R04558 GLUTAMIDOTRANS-RXN Phosphoribulosylformimino-AICAR-P + L-Glutamine > Hydrogen ion + L-Glutamate + D-Erythro-imidazole-glycerol-phosphate + AICAR GLUTAMIDOTRANS-RXN D-Erythro-imidazole-glycerol-phosphate > Imidazole acetol-phosphate + Water IMIDPHOSDEHYD-RXN Phosphoribulosylformimino-AICAR-P + L-Glutamine > L-Glutamic acid + Hydrogen ion + 5-Amino-4-imidazolecarboxyamide + D-Erythro-imidazole-glycerol-phosphate + L-Glutamate PW_R002869