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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:21:31 UTC
Update Date2017-10-23 19:06:01 UTC
HMDB IDHMDB0012236
Secondary Accession Numbers
  • HMDB12236
Metabolite Identification
Common NameImidazole acetol-phosphate
DescriptionImidazole acetol-phosphate is involved in the histidine biosynthesis I pathway. Imidazole acetol-phosphate is created by the breakdown of D-erythro-imidazole-glycerol-phosphate into imidazole acetol-phosphate and H2O. Imidazoleglycerol-phosphate dehydratase catalyzes this reaction. Imidazole acetol-phosphate reacts with L-glutamate to produce L-histidinol-phosphate and 2-ketoglutarate. Histidinol-phosphate aminotransferase catalyzes this reaction.
Structure
Thumb
Synonyms
ValueSource
3-(Imidazol-4-yl)-2-oxopropyl phosphateChEBI
Imidazole-acetol phosphateChEBI
3-(Imidazol-4-yl)-2-oxopropyl phosphoric acidGenerator
Imidazole acetol-phosphoric acidGenerator
Imidazole-acetol phosphoric acidGenerator
1-(1H-Imidazol-4-yl)-3-(phosphonooxy)-2-propanoneHMDB
3-(1H-Imidazol-4-yl)-2-oxopropyl dihydrogen phosphateHMDB
3-(Imidazol-4-yl)-2-oxopropyl dihydrogen phosphateHMDB
Imidazole acetol phosphateHMDB
Imidazole acetol-PHMDB
Chemical FormulaC6H9N2O5P
Average Molecular Weight220.1198
Monoisotopic Molecular Weight220.02490792
IUPAC Name[3-(1H-imidazol-4-yl)-2-oxopropoxy]phosphonic acid
Traditional Name3-(1H-imidazol-4-yl)-2-oxopropoxyphosphonic acid
CAS Registry Number99979-59-6
SMILES
OP(O)(=O)OCC(=O)CC1=CNC=N1
InChI Identifier
InChI=1S/C6H9N2O5P/c9-6(3-13-14(10,11)12)1-5-2-7-4-8-5/h2,4H,1,3H2,(H,7,8)(H2,10,11,12)
InChI KeyYCFFMSOLUMRAMD-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassOrganic phosphoric acids and derivatives
Direct ParentMonoalkyl phosphates
Alternative Parents
Substituents
  • Monoalkyl phosphate
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Ketone
  • Organoheterocyclic compound
  • Azacycle
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility14.9 g/LALOGPS
logP-0.9ALOGPS
logP-3ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)6.65ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area112.51 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity46.07 m³·mol⁻¹ChemAxon
Polarizability18.15 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-9200000000-41a681dee161ad4f3e7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-3390000000-102fb9b517f2001e0996View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-4950000000-076be23324f875b841dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9500000000-99bd6a8eac665bc00868View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-7190000000-c52bfb05c2cd90023536View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-7598c15214a6b2b67038View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-59a5e26dad504ee2412dView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB028879
KNApSAcK IDNot Available
Chemspider ID770
KEGG Compound IDC01267
BioCyc IDIMIDAZOLE-ACETOL-P
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound792
PDB IDNot Available
ChEBI ID16426
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. AMES BN, HORECKER BL: The biosynthesis of histidine: imidazoleacetol phosphate transaminase. J Biol Chem. 1956 May;220(1):113-28. [PubMed:13319331 ]
  2. Albritton WL, Levin AP: Some comparative kinetic data on the enzyme imidazoleacetol phosphate:L-glutamate aminotransferase derived from mutant strains of Salmonella typhimurium. J Biol Chem. 1970 May 25;245(10):2525-8. [PubMed:5445798 ]
  3. AMES BN, MITCHELL HK: The biosynthesis of histidine; imidazoleglycerol phosphate, imidazoleacetol phosphate, and histidinol phosphate. J Biol Chem. 1955 Feb;212(2):687-96. [PubMed:14353870 ]
  4. LEVIN AP, HARTMAN PE: ACTION OF A HISTIDINE ANALOGUE, 1,2,4-TRIAZOLE-3-ALANINE, IN SALMONELLA TYPHIMURIUM. J Bacteriol. 1963 Oct;86:820-8. [PubMed:14066480 ]
  5. Henderson GB, Snell EE: Vitamin B 6 -responsive histidine deficiency in mutants of Salmonella typhimurium. Proc Natl Acad Sci U S A. 1971 Dec;68(12):2903-7. [PubMed:4943547 ]