2.0 2012-05-31 13:59:09 -0600 2015-09-13 12:56:13 -0600 ECMDB03431 M2MDB000502 L-Histidinol L-Histidinol is a structural analogue of the essential amino acid L-histidine. It is an intermediate in histidine metabolism. It is converted to L-histidinal via bifunctional histidinal dehydrogenase/histidinol dehydrogenase (EC:1.1.1.23). (KEGG) (S)-b-amino-1H-Imidazole-4-propanol (S)-beta-Amino-1H-imidazole-4-propanol (S)-β-amino-1H-Imidazole-4-propanol Histidinol Histidol HSO Imidazole C-4(5) deriv. 4 L-histidinol C6H11N3O 141.171 141.090211989 (2S)-2-amino-3-(1H-imidazol-5-yl)propan-1-ol HSO 4836-52-6 N[C@H](CO)CC1=CN=CN1 InChI=1S/C6H11N3O/c7-5(3-10)1-6-2-8-4-9-6/h2,4-5,10H,1,3,7H2,(H,8,9)/t5-/m0/s1 ZQISRDCJNBUVMM-YFKPBYRVSA-N Solid Cytosol logp -1.10 ALOGPS logs -0.00 ALOGPS solubility 1.40e+02 g/l ALOGPS logp -1.7 ChemAxon pka_strongest_acidic 13.45 ChemAxon pka_strongest_basic 9.41 ChemAxon iupac (2S)-2-amino-3-(1H-imidazol-5-yl)propan-1-ol ChemAxon average_mass 141.171 ChemAxon mono_mass 141.090211989 ChemAxon smiles N[C@H](CO)CC1=CN=CN1 ChemAxon formula C6H11N3O ChemAxon inchi InChI=1S/C6H11N3O/c7-5(3-10)1-6-2-8-4-9-6/h2,4-5,10H,1,3,7H2,(H,8,9)/t5-/m0/s1 ChemAxon inchikey ZQISRDCJNBUVMM-YFKPBYRVSA-N ChemAxon polar_surface_area 74.93 ChemAxon refractivity 38.19 ChemAxon polarizability 14.74 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 2 ChemAxon formal_charge 0 ChemAxon 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 847 Specdb::CMs 848 Specdb::CMs 849 Specdb::CMs 850 Specdb::CMs 3340 Specdb::CMs 30204 Specdb::CMs 30310 Specdb::CMs 30597 Specdb::CMs 30792 Specdb::CMs 38600 Specdb::CMs 163783 Specdb::NmrOneD 1970 Specdb::NmrOneD 4949 Specdb::NmrOneD 4950 Specdb::NmrOneD 21882 Specdb::NmrOneD 21883 Specdb::NmrOneD 21884 Specdb::NmrOneD 21885 Specdb::NmrOneD 21886 Specdb::NmrOneD 21887 Specdb::NmrOneD 21888 Specdb::NmrOneD 21889 Specdb::NmrOneD 21890 Specdb::NmrOneD 21891 Specdb::NmrOneD 21892 Specdb::NmrOneD 21893 Specdb::NmrOneD 21894 Specdb::NmrOneD 21895 Specdb::NmrOneD 21896 Specdb::NmrOneD 21897 Specdb::NmrOneD 21898 Specdb::NmrOneD 21899 Specdb::NmrOneD 21900 Specdb::NmrOneD 21901 Specdb::MsMs 2307 Specdb::MsMs 2308 Specdb::MsMs 2309 Specdb::MsMs 5947 Specdb::MsMs 5948 Specdb::MsMs 5949 Specdb::MsMs 5950 Specdb::MsMs 5951 Specdb::MsMs 5956 Specdb::MsMs 179958 Specdb::MsMs 179959 Specdb::MsMs 179960 Specdb::MsMs 182292 Specdb::MsMs 182293 Specdb::MsMs 182294 Specdb::MsMs 446315 Specdb::MsMs 446316 Specdb::MsMs 446317 Specdb::MsMs 446318 Specdb::MsMs 446319 Specdb::MsMs 448034 Specdb::MsMs 2227347 Specdb::MsMs 2227387 Specdb::MsMs 2229672 Specdb::MsMs 2231983 Specdb::NmrTwoD 1905 HMDB03431 165271 144886 C00860 16255 HISTIDINOL 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 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 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 Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. 19212411 Raju RV, Datla RS, Warrington RC, Sharma RK: Effects of L-histidine and its structural analogues on human N-myristoyltransferase activity and importance of EEVEH amino acid sequence for enzyme activity. Biochemistry. 1998 Oct 20;37(42):14928-36. 9778369 Warrington RC, Cheng I, Zhang L, Fang WD: L-histidinol increases the vulnerability of cultured human leukemia and lymphoma cells to anticancer drugs. Anticancer Res. 1993 Nov-Dec;13(6A):2107-12. 8297120 Warrington RC, Norum JN, Hilchey JL, Watt C, Fang WD: A simple, informative, and quantitative flow cytometric method for assessing apoptosis in cultured cells. Prog Neuropsychopharmacol Biol Psychiatry. 2003 Apr;27(2):231-43. 12657362 Beltra, A. P.; Bonete, P.; Gonzalez-Garcia, J.; Garcia-Garcia, V.; Montiel, V. Electrochemical synthesis of L-histidinol using solvated electrons. Journal of the Electrochemical Society (2005), 152(4), D65-D68. http://hmdb.ca/system/metabolites/msds/000/003/012/original/HMDB03431.pdf?1358461610 Histidine biosynthesis bifunctional protein hisB P06987 HIS7_ECOLI hisB http://ecmdb.ca/proteins/P06987.xml Histidinol dehydrogenase P06988 HISX_ECOLI hisD http://ecmdb.ca/proteins/P06988.xml Water + L-Histidinol + 2 NAD >3 Hydrogen ion + L-Histidine +2 NADH Water + Histidinol phosphate <> L-Histidinol + Phosphate R03013 HISTIDPHOS-RXN L-Histidinol + NAD <> L-Histidinal + NADH + Hydrogen ion R03012 Histidinol phosphate + Water > L-Histidinol + Phosphate HISTIDPHOS-RXN L-Histidinol + NAD > Hydrogen ion + histidinal + NADH HISTOLDEHYD-RXN Histidinol phosphate + Water > L-Histidinol + Inorganic phosphate L-Histidinol + Water + 2 NAD > L-Histidine +2 NADH L-Histidinol + 2 NAD + Water <> L-Histidine +2 NADH +3 Hydrogen ion R01158 L-histidinol-phosphate + Water > Phosphate + L-Histidinol PW_R002872 L-Histidinol + NAD > NADH + Hydrogen ion + Histidinal PW_R002873 Water + Histidinol phosphate <> L-Histidinol + Phosphate Water + Histidinol phosphate <> L-Histidinol + Phosphate 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 12.8 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 51200 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 19.2 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 76800 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 19.6 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 78400 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