imidazole acetol-phosphate (PAMDB110032)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110032
Identification
Name: imidazole acetol-phosphate
Description:Dianion of 3-(imidazol-4-yl)-2-oxopropyl dihydrogen phosphate arising from deprotonation of both phosphate OH groups; major species at pH 7.3.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • imidazole acetol-P
  • 3-(imidazol-4-yl)-2-oxopropyl phosphate
Chemical Formula: C6H7N2O5P
Average Molecular Weight: 218.1
Monoisotopic Molecular Weight: 220.0249079198
InChI Key: YCFFMSOLUMRAMD-UHFFFAOYSA-L
InChI: 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)/p-2
CAS number: 99979-59-6
IUPAC Name:3-(1H-imidazol-4-yl)-2-oxopropyl phosphate
Traditional IUPAC Name: 3-(1H-imidazol-4-yl)-2-oxopropoxyphosphonic acid
SMILES:C1(NC=NC=1CC(COP([O-])(=O)[O-])=O)
Chemical Taxonomy
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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassOrganic phosphoric acids and derivatives
Direct Parent Monoalkyl 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 Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
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 Solubility14.9 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity46.07 m3·mol-1ChemAxon
Polarizability18.15 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
  • superpathway of histidine, purine, and pyrimidine biosynthesisPRPP-PWY
  • L-histidine biosynthesisHISTSYN-PWY
    Spectra
    Spectra:
    Spectrum TypeDescriptionSplash Key
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
    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
    References
    References:
    • AMES BN, HORECKER BL: The biosynthesis of histidine: imidazoleacetol phosphate transaminase. J Biol Chem. 1956 May;220(1):113-28. [13319331 ]
    • 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. [5445798 ]
    • AMES BN, MITCHELL HK: The biosynthesis of histidine; imidazoleglycerol phosphate, imidazoleacetol phosphate, and histidinol phosphate. J Biol Chem. 1955 Feb;212(2):687-96. [14353870 ]
    • 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. [14066480 ]
    • 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. [4943547 ]
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    CAS99979-59-6
    ChEBI57766
    HMDBHMDB12236
    IAF126037231
    KEGGC01267
    PubChem25244516