2.0 2012-05-31 10:23:03 -0600 2015-09-13 12:56:06 -0600 ECMDB00177 M2MDB000074 L-Histidine Histidine is an amino acid. It is a precursor for histamine and carnosine biosynthesis. The enzyme histidine ammonia-lyase converts histidine into ammonia and urocanic acid. (Wikipedia) α-amino-4-imidazoleproprionate α-amino-4-imidazoleproprionic acid (S)-α-amino-1H-imidazole-4-propanoate (S)-α-amino-1H-imidazole-4-propanoic acid (S)-1H-Imidazole-4-alanine (S)-2-Amino-3-(4-imidazolyl)propionsaeure (S)-4-(2-Amino-2-carboxyethyl)imidazole (S)-a-Amino-1H-imidazole-4-propanoate (S)-a-Amino-1H-imidazole-4-propanoic acid (S)-a-amino-1H-Imidazole-4-propionate (S)-a-amino-1H-Imidazole-4-propionic acid (S)-alpha-Amino-1H-imidazole-4-propanoate (S)-alpha-Amino-1H-imidazole-4-propanoic acid (S)-alpha-Amino-1H-imidazole-4-propionate (S)-alpha-Amino-1H-imidazole-4-propionic acid (S)-Histidine (S)-α-amino-1H-Imidazole-4-propanoate (S)-α-amino-1H-Imidazole-4-propanoic acid (S)-α-amino-1H-Imidazole-4-propionate (S)-α-amino-1H-Imidazole-4-propionic acid (S)1H-Imidazole-4-alanine 3-(1H-Imidazol-4-yl)-L-Alanine a-amino-4-Imidazoleproprionate a-amino-4-Imidazoleproprionic acid Alpha-Amino-4-imidazoleproprionate Alpha-Amino-4-imidazoleproprionic acid Amino-1H-imidazole-4-propanoate Amino-1H-imidazole-4-propanoic acid Amino-4-imidazoleproprionate Amino-4-imidazoleproprionic acid Glyoxaline-5-alanine H His Histidine L-(-)-Histidine α-amino-4-Imidazoleproprionate α-amino-4-Imidazoleproprionic acid C6H9N3O2 155.1546 155.069476547 (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid L-histidine 71-00-1 N[C@@H](CC1=CN=CN1)C(O)=O InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1 HNDVDQJCIGZPNO-YFKPBYRVSA-N Solid Cytosol Extra-organism Periplasm logp -2.67 ALOGPS logs -0.34 ALOGPS solubility 7.13e+01 g/l ALOGPS melting_point 287 oC logp -3.6 ChemAxon pka_strongest_acidic 1.85 ChemAxon pka_strongest_basic 9.44 ChemAxon iupac (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid ChemAxon average_mass 155.1546 ChemAxon mono_mass 155.069476547 ChemAxon smiles N[C@@H](CC1=CN=CN1)C(O)=O ChemAxon formula C6H9N3O2 ChemAxon inchi InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1 ChemAxon inchikey HNDVDQJCIGZPNO-YFKPBYRVSA-N ChemAxon polar_surface_area 92 ChemAxon refractivity 38.06 ChemAxon polarizability 14.67 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Aminoacyl-tRNA biosynthesis ec00970 Histidine metabolism ec00340 beta-Alanine metabolism The Beta-Alanine Metabolism starts with a product of Aspartate metabolism. Aspartate is decarboxylated by aspartate 1-decarboxylase, releasing carbon dioxide and Beta-alanine. Beta alanine is then metabolized through a pantothenate synthetase resulting in Pantothenic acid undergoes phosphorylation through a ATP driven pantothenate kinase, resulting in D-4-phosphopantothenate. Pantothenate (vitamin B5) is the universal precursor for the synthesis of the 4'-phosphopantetheine moiety of coenzyme A and acyl carrier protein. Only plants and microorganismscan synthesize pantothenate de novo - animals require a dietary supplement. The enzymes of this pathway are therefore considered to be antimicrobial drug targets. PW000896 ec00410 Metabolic ABC transporters ec02010 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 tRNA Charging 2 This pathway groups together all E. coli tRNA charging reactions. PW000803 Metabolic tRNA charging This pathway groups together all E. coli tRNA charging reactions. PW000799 Metabolic tRNA charging TRNA-CHARGING-PWY histidine biosynthesis HISTSYN-PWY Specdb::CMs 416 Specdb::CMs 417 Specdb::CMs 418 Specdb::CMs 419 Specdb::CMs 1646 Specdb::CMs 1833 Specdb::CMs 3063 Specdb::CMs 30203 Specdb::CMs 30309 Specdb::CMs 30596 Specdb::CMs 30739 Specdb::CMs 30768 Specdb::CMs 31051 Specdb::CMs 31052 Specdb::CMs 31961 Specdb::CMs 31962 Specdb::CMs 37340 Specdb::CMs 157409 Specdb::CMs 1052791 Specdb::CMs 1052793 Specdb::CMs 1052795 Specdb::CMs 1052797 Specdb::CMs 1052799 Specdb::EiMs 1976 Specdb::NmrOneD 1146 Specdb::NmrOneD 1193 Specdb::NmrOneD 142730 Specdb::NmrOneD 142731 Specdb::NmrOneD 142732 Specdb::NmrOneD 142733 Specdb::NmrOneD 142734 Specdb::NmrOneD 142735 Specdb::NmrOneD 142736 Specdb::NmrOneD 142737 Specdb::NmrOneD 142738 Specdb::NmrOneD 142739 Specdb::NmrOneD 142740 Specdb::NmrOneD 142741 Specdb::NmrOneD 142742 Specdb::NmrOneD 142743 Specdb::NmrOneD 142744 Specdb::NmrOneD 142745 Specdb::NmrOneD 142746 Specdb::NmrOneD 142747 Specdb::NmrOneD 142748 Specdb::NmrOneD 142749 Specdb::NmrOneD 166370 Specdb::NmrOneD 166434 Specdb::NmrOneD 166541 Specdb::MsMs 283 Specdb::MsMs 284 Specdb::MsMs 285 Specdb::MsMs 3351 Specdb::MsMs 3352 Specdb::MsMs 3353 Specdb::MsMs 3354 Specdb::MsMs 3355 Specdb::MsMs 3356 Specdb::MsMs 3357 Specdb::MsMs 3358 Specdb::MsMs 3359 Specdb::MsMs 3360 Specdb::MsMs 3361 Specdb::MsMs 3362 Specdb::MsMs 3363 Specdb::MsMs 3364 Specdb::MsMs 3365 Specdb::MsMs 3366 Specdb::MsMs 3367 Specdb::MsMs 3368 Specdb::MsMs 3369 Specdb::MsMs 3370 Specdb::MsMs 3371 Specdb::MsMs 3372 Specdb::NmrTwoD 1189 HMDB00177 6274 6038 C00135 15971 HIS HIS_LFZW_DHE2 L-Histidine 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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Organic letters (2002), 4(21), 3767-9. http://hmdb.ca/system/metabolites/msds/000/000/126/original/HMDB00177.pdf?1358894676 Histidinol dehydrogenase P06988 HISX_ECOLI hisD http://ecmdb.ca/proteins/P06988.xml Histidine transport ATP-binding protein hisP P07109 HISP_ECOLI hisP http://ecmdb.ca/proteins/P07109.xml Histidyl-tRNA synthetase P60906 SYH_ECOLI hisS http://ecmdb.ca/proteins/P60906.xml Histidine transport system permease protein hisM P0AEU3 HISM_ECOLI hisM http://ecmdb.ca/proteins/P0AEU3.xml Histidine transport system permease protein hisQ P52094 HISQ_ECOLI hisQ http://ecmdb.ca/proteins/P52094.xml Histidine-binding periplasmic protein P0AEU0 HISJ_ECOLI hisJ http://ecmdb.ca/proteins/P0AEU0.xml Histidine transport ATP-binding protein hisP P07109 HISP_ECOLI hisP http://ecmdb.ca/proteins/P07109.xml Uncharacterized amino-acid ABC transporter ATP-binding protein yecC P37774 YECC_ECOLI yecC http://ecmdb.ca/proteins/P37774.xml Inner membrane amino-acid ABC transporter permease protein yecS P0AFT2 YECS_ECOLI yecS http://ecmdb.ca/proteins/P0AFT2.xml Histidine transport system permease protein hisM P0AEU3 HISM_ECOLI hisM http://ecmdb.ca/proteins/P0AEU3.xml Aromatic amino acid transport protein AroP P15993 AROP_ECOLI aroP http://ecmdb.ca/proteins/P15993.xml Histidine transport system permease protein hisQ P52094 HISQ_ECOLI hisQ http://ecmdb.ca/proteins/P52094.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Histidine-binding periplasmic protein P0AEU0 HISJ_ECOLI hisJ http://ecmdb.ca/proteins/P0AEU0.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Adenosine triphosphate + Water + L-Histidine > ADP + Hydrogen ion + L-Histidine + Phosphate ABC-14-RXN Adenosine triphosphate + Water + L-Histidine > ADP + Hydrogen ion + L-Histidine + Phosphate ABC-14-RXN Water + L-Histidinol + 2 NAD >3 Hydrogen ion + L-Histidine +2 NADH Adenosine triphosphate + L-Histidine + tRNA(His) + tRNA(His) <> Adenosine monophosphate + L-Histidyl-tRNA(His) + Pyrophosphate + L-Histidyl-tRNA(His) R03655 L-Histidinal + Water + NAD <> L-Histidine + NADH + Hydrogen ion R01163 Adenosine triphosphate + L-Histidine + tRNA(His) <> Adenosine monophosphate + Pyrophosphate + L-Histidyl-tRNA(His) R03655 Adenosine triphosphate + L-Histidine + Water > ADP + Phosphate + L-Histidine + Hydrogen ion ABC-14-RXN Adenosine triphosphate + L-Histidine + Water > ADP + Phosphate + L-Histidine + Hydrogen ion ABC-14-RXN histidinal + NAD + Water > Hydrogen ion + L-Histidine + NADH HISTALDEHYD-RXN ala-his + Water > L-Alanine + L-Histidine RXN0-6978 L-Histidinol + Water + 2 NAD > L-Histidine +2 NADH Adenosine triphosphate + L-Histidine + tRNA(His) > Adenosine monophosphate + Pyrophosphate + L-histidyl-tRNA(His) L-Histidinol + 2 NAD + Water <> L-Histidine +2 NADH +3 Hydrogen ion R01158 L-Histidine + Adenosine triphosphate + Hydrogen ion + tRNA(His) + L-Histidine > Adenosine monophosphate + Pyrophosphate + L-histidyl-tRNA(His) PW_R002839 Water + NAD + Histidinal >2 Hydrogen ion + NADH + L-Histidine + L-Histidine PW_R002874 L-Histidine + Adenosine triphosphate + Water + L-Histidine > Adenosine diphosphate + Phosphate + Hydrogen ion + L-Histidine + ADP PW_RCT000109 Adenosine triphosphate + L-Histidine + tRNA(His) <> Adenosine monophosphate + L-Histidyl-tRNA(His) + Pyrophosphate L-Histidinal + Water + NAD <> L-Histidine + NADH + Hydrogen ion Adenosine triphosphate + L-Histidine + tRNA(His) <> Adenosine monophosphate + L-Histidyl-tRNA(His) + Pyrophosphate Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose Shake flask and filter culture 67.6 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 270400 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol Shake flask and filter culture 175.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 700000 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate Shake flask and filter culture 97.5 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 390000 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 52.4 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 209600 0 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776 Luria-Bertani (LB) media Shake flask 235.33 uM true 25.7 37 oC BL21 DE3 Stationary phase cultures (overnight culture) 941333 102788 Lin, Z., Johnson, L. C., Weissbach, H., Brot, N., Lively, M. O., Lowther, W. T. (2007). "Free methionine-(R)-sulfoxide reductase from Escherichia coli reveals a new GAF domain function." Proc Natl Acad Sci U S A 104:9597-9602. 17535911 Luria-Bertani (LB) media Shake flask 0.22 uM true 0.01 37 oC BL21 DE3 Stationary phase cultures (overnight culture) 871 34 Lin, Z., Johnson, L. C., Weissbach, H., Brot, N., Lively, M. O., Lowther, W. T. (2007). "Free methionine-(R)-sulfoxide reductase from Escherichia coli reveals a new GAF domain function." Proc Natl Acad Sci U S A 104:9597-9602. 17535911