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Record Information
Version	2.0
Creation Date	2012-05-31 13:59:09 -0600
Update Date	2015-09-13 12:56:13 -0600
Secondary Accession Numbers	ECMDB03431
Identification
Name:	L-Histidinol
Description	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)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xae650834> Close
Synonyms:	(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
Chemical Formula:	C6H11N3O
Weight:	Average: 141.171 Monoisotopic: 141.090211989
InChI Key:	ZQISRDCJNBUVMM-YFKPBYRVSA-N
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
CAS number:	4836-52-6
IUPAC Name:	(2S)-2-amino-3-(1H-imidazol-5-yl)propan-1-ol
Traditional IUPAC Name:	HSO
SMILES:	N[C@H](CO)CC1=CN=CN1
Chemical Taxonomy
Description	belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
Kingdom	Organic compounds
Super Class	Organic nitrogen compounds
Class	Organonitrogen compounds
Sub Class	Amines
Direct Parent	Aralkylamines
Alternative Parents	Imidazoles Heteroaromatic compounds 1,2-aminoalcohols Azacyclic compounds Primary alcohols Organopnictogen compounds Monoalkylamines Hydrocarbon derivatives
Substituents	Aralkylamine Azole Imidazole Heteroaromatic compound 1,2-aminoalcohol Azacycle Organoheterocyclic compound Organic oxygen compound Primary amine Primary alcohol Organooxygen compound Primary aliphatic amine Alcohol Hydrocarbon derivative Organopnictogen compound Aromatic heteromonocyclic compound
Molecular Framework	Aromatic heteromonocyclic compounds
External Descriptors	imidazoles (CHEBI:16255 ) amino alcohol (CHEBI:16255 )
Physical Properties
State:	Solid
Charge:	2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 140 g/L ALOGPS logP -1.1 ALOGPS logP -1.7 ChemAxon logS 0 ALOGPS pKa (Strongest Acidic) 13.45 ChemAxon pKa (Strongest Basic) 9.41 ChemAxon Physiological Charge 2 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 74.93 Ų ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 38.19 m³·mol⁻¹ ChemAxon Polarizability 14.74 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Water + L-Histidinol + 2 NAD >3 Hydrogen ion + L-Histidine +2 NADH Water + Histidinol phosphate <> L-Histidinol + Phosphate L-Histidinol + NAD <> L-Histidinal + NADH + Hydrogen ion Histidinol phosphate + Water > L-Histidinol + Phosphate L-Histidinol + NAD > Hydrogen ion + histidinal + NADH 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 L-histidinol-phosphate + Water > Phosphate + L-Histidinol L-Histidinol + NAD > NADH + Hydrogen ion + Histidinal Water + Histidinol phosphate <> L-Histidinol + Phosphate Water + Histidinol phosphate <> L-Histidinol + Phosphate
SMPDB Pathways:	Secondary Metabolites: Histidine biosynthesis PW000984 histidine biosynthesis PW000810
KEGG Pathways:	Histidine metabolism ec00340 Metabolic pathways eco01100
EcoCyc Pathways:	histidine biosynthesis HISTSYN-PWY
Concentrations
	Concentration Strain Media Growth Status Growth System Temperature Details 13± 0 uM K12 NCM3722 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 Mid-Log Phase Shake flask and filter culture 37 oC PMID: 19561621 19± 0 uM K12 NCM3722 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 Mid-Log Phase Shake flask and filter culture 37 oC PMID: 19561621 20± 0 uM K12 NCM3722 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 Mid-Log Phase Shake flask and filter culture 37 oC PMID: 19561621 Find out more about how we convert literature concentrations.
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) splash10-0udi-1970000000-5f8fce52ae008e9577d3 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) splash10-0udi-1960000000-2bd5915e1e2204265b30 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) splash10-0udi-0960000000-04ea4478dfe81318bf5c View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) splash10-0fk9-9540000000-9d5008be3cb2086af6f4 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0udi-1970000000-5f8fce52ae008e9577d3 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0udi-1960000000-2bd5915e1e2204265b30 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0udi-0960000000-04ea4478dfe81318bf5c View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-0fk9-9540000000-9d5008be3cb2086af6f4 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-03di-5900000000-b7271e5101b1cf971b24 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive splash10-03e9-9800000000-eb7ec98ac413a4a5067d View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-006x-1900000000-c360dc1772243d0c7cca View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-001i-9000000000-eba5a77ea4a62d8375f8 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-001i-9000000000-009922321d7904037f80 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive splash10-0006-0900000000-3a563827d1023d4dadd7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive splash10-00e9-7900000000-4baa9781af4596ef1a49 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive splash10-001i-9000000000-98f4a65357b52f544e0c View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive splash10-001i-9000000000-5921f5ed9c6159fbe48e View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive splash10-001i-9000000000-a7a82388a3feef766362 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive splash10-0089-8900000000-b7fa72e4e20dbc5d79d2 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-0006-0900000000-3a563827d1023d4dadd7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-00e9-7900000000-4baa9781af4596ef1a49 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-001i-9000000000-98f4a65357b52f544e0c View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-001i-9000000000-5921f5ed9c6159fbe48e View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QQ , positive splash10-001i-9000000000-128590ab44ecade57be8 View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF , positive splash10-0089-8900000000-b7fa72e4e20dbc5d79d2 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Negative splash10-0006-0900000000-407552f60d560106c1a3 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Positive splash10-00di-0900000000-fdf0dfe513943a57b5ff View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Negative splash10-052u-0900000000-c9d458943690ec68d5cc View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Positive splash10-00di-0900000000-bb10166bbd4c200cca41 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-006x-0900000000-e19200b81166dd2ceb6c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0abc-3900000000-8073bbe0237addc54c81 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a5a-9300000000-a833e6da71592c915e87 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0006-1900000000-f2eb428fd58c551e9f84 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0596-9800000000-7dcca6b55761d69a3dc2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-000x-9100000000-4649be9a2b45a85f4de1 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	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. Pubmed: 19561621 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. Pubmed: 22080510 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. Pubmed: 21097882 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. Pubmed: 9778369 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. Pubmed: 19212411 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. Pubmed: 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. Pubmed: 12657362 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. Pubmed: 18331064
Synthesis Reference:	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.
Material Safety Data Sheet (MSDS)	Download (PDF)
Links
External Links:	Resource Link CHEBI ID 16255 HMDB ID HMDB03431 Pubchem Compound ID 165271 Kegg ID C00860 ChemSpider ID 144886 Wikipedia ID Not Available BioCyc ID HISTIDINOL EcoCyc ID HISTIDINOL

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