ECMDB: L-Histidinol (ECMDB03431) (M2MDB000502)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)XML

Proteins (651)

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

MOL SDF PDB SMILES InChI

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

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:

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 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	38.19 m³·mol⁻¹	ChemAxon
Polarizability	14.74 Å³	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

Enzymes

Protein Details

1. Histidine biosynthesis bifunctional protein hisB

General function:: Involved in catalytic activity
Specific function:: D-erythro-1-(imidazol-4-yl)glycerol 3- phosphate = 3-(imidazol-4-yl)-2-oxopropyl phosphate + H(2)O
Gene Name:: hisB
Uniprot ID:: P06987
Molecular weight:: 40278

Reactions

D-erythro-1-(imidazol-4-yl)glycerol 3-phosphate = 3-(imidazol-4-yl)-2-oxopropyl phosphate + H(2)O.
L-histidinol phosphate + H(2)O = L-histidinol + phosphate.

Protein Details

2. Histidinol dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the sequential NAD-dependent oxidations of L- histidinol to L-histidinaldehyde and then to L-histidine
Gene Name:: hisD
Uniprot ID:: P06988
Molecular weight:: 46110

Reactions

L-histidinol + H(2)O + 2 NAD(+) = L-histidine + 2 NADH.

L-Histidinol (ECMDB03431) (M2MDB000502)

Structure for #<Compound:0xaeda7b8c>

Enzymes

Reactions

Reactions