histidinol (PAMDB110046)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110046
Identification
Name: histidinol
Description:An amino alcohol that is propanol substituted by 1H-imidazol-4-yl group at position 3 and an amino group at position 2 (the 2S stereoisomer).
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • histidol
  • L-histidinol
Chemical Formula: C6H12N3O
Average Molecular Weight: 142.18
Monoisotopic Molecular Weight: 142.0980370229
InChI Key: ZQISRDCJNBUVMM-YFKPBYRVSA-O
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)/p+1/t5-/m0/s1
CAS number: 4836-52-6
IUPAC Name:(2S)-2-amino-3-(1H-imidazol-4-yl)propan-1-ol
Traditional IUPAC Name: HSO
SMILES:C1(NC=NC=1CC(CO)[N+])
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic nitrogen compounds
Sub ClassOrganonitrogen compounds
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
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility129.0 mg/mLALOGPS
logP-1.3ALOGPS
logP-1.7ChemAxon
logS-0.04ALOGPS
pKa (Strongest Acidic)13.45ChemAxon
pKa (Strongest Basic)9.41ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area74.93 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.19 m3·mol-1ChemAxon
Polarizability14.74 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
histidinol + NAD+ + Water → L-Histidine + NADH + Hydrogen ion
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0udi-1970000000-5f8fce52ae008e9577d3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0udi-1960000000-2bd5915e1e2204265b30View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0udi-0960000000-04ea4478dfe81318bf5cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0fk9-9540000000-9d5008be3cb2086af6f4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-006x-1900000000-c360dc1772243d0c7ccaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-eba5a77ea4a62d8375f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-009922321d7904037f80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-0900000000-3a563827d1023d4dadd7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00e9-7900000000-4baa9781af4596ef1a49View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-9000000000-98f4a65357b52f544e0cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-9000000000-5921f5ed9c6159fbe48eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001i-9000000000-a7a82388a3feef766362View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0089-8900000000-b7fa72e4e20dbc5d79d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Warrington RC, Cheng I, Fang W (1991)Effects of L-histidinol on the proliferation and anticancer drug susceptibility of cultured B16f10 melanoma cells. Anticancer research 11, Pubmed: 1768057
  • Gaber RF, Kielland-Brandt MC, Fink GR (1990)HOL1 mutations confer novel ion transport in Saccharomyces cerevisiae. Molecular and cellular biology 10, Pubmed: 2405251
  • Zaharko D, Plowman J, Waud W, Dykes D, Malspeis L (1992)L-histidinol: preclinical therapeutic studies in combination with antitumor agents and pharmacokinetic studies in mice. Cancer research 52, Pubmed: 1617631
  • Andorn N, Aronovitch J (1982)Purification and properties of histidinol dehydrogenase from Escherichia coli B. Journal of general microbiology 128, Pubmed: 7042909
  • Kohnoe S, Maehara Y, Takahashi I, Yoshida M, Emi Y, Baba H, Sugimachi K (1993)L-histidinol potentiates hyperthermic cell-killing in-vitro. International journal of oncology 3, Pubmed: 21573440
  • Stolfi RL, Martin DS (1990)Chemotherapeutic activity of L-histidinol against spontaneous, autochthonous murine breast tumors. Chemotherapy 36, Pubmed: 2292205
  • Raju RV, Datla RS, Warrington RC, Sharma RK (1998)Effects of L-histidine and its structural analogues on human N-myristoyltransferase activity and importance of EEVEH amino acid sequence for enzyme activity. Biochemistry 37, Pubmed: 9778369
  • Warrington RC, Fang WD, Zhang L, Shieh M, Saier MH (1996)Mimetics of L-histidinol which selectively modulate daunomycin toxicity in normal and tumorigenic epithelial cells. Anticancer research 16, Pubmed: 9042234
  • Warrington RC, Cheng I, Zhang L, Fang WD (1993)L-histidinol increases the vulnerability of cultured human leukemia and lymphoma cells to anticancer drugs. Anticancer research 13, Pubmed: 8297120
  • Warrington RC, Wratten N, Hechtman R (1977)L-Histidinol inhibits specifically and reversibly protein and ribosomal RNA synthesis in mouse L cells. The Journal of biological chemistry 252, Pubmed: 885850
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)
External Links:
ResourceLink
CAS501-28-0
ChEBI6241
HMDBHMDB03431
IAF126036226
KEGGC00860
KNApSAcKC00007479
PubChem25244116