Record Information
Version2.0
Creation Date2012-05-31 14:21:11 -0600
Update Date2015-06-03 17:19:03 -0600
Secondary Accession Numbers
  • ECMDB12236
Identification
Name:Imidazole acetol-phosphate
Description:Imidazole acetol-phosphate is involved in the histidine biosynthesis 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.
Structure
Thumb
Synonyms:
  • 1-(1H-Imidazol-4-yl)-3-(phosphonooxy)-2-propanone
  • 3-(1H-Imidazol-4-yl)-2-oxopropyl dihydrogen phosphate
  • 3-(1H-Imidazol-4-yl)-2-oxopropyl dihydrogen phosphoric acid
  • 3-(Imidazol-4-yl)-2-oxopropyl dihydrogen phosphate
  • 3-(Imidazol-4-yl)-2-oxopropyl dihydrogen phosphoric acid
  • 3-(Imidazol-4-yl)-2-oxopropyl phosphate
  • 3-(Imidazol-4-yl)-2-oxopropyl phosphoric acid
  • IAP
  • Imidazole acetol phosphate
  • Imidazole acetol phosphoric acid
  • Imidazole acetol-p
  • Imidazole acetol-phosphoric acid
  • Imidazole-acetol phosphate
  • Imidazole-acetol phosphoric acid
Chemical Formula:C6H9N2O5P
Weight:Average: 220.1198
Monoisotopic: 220.02490792
InChI Key:YCFFMSOLUMRAMD-UHFFFAOYSA-N
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)
CAS number:99979-59-6
IUPAC Name:[3-(1H-imidazol-4-yl)-2-oxopropoxy]phosphonic acid
Traditional IUPAC Name:3-(1H-imidazol-4-yl)-2-oxopropoxyphosphonic acid
SMILES:OP(O)(=O)OCC(=O)CC1=CNC=N1
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
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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:Cytoplasm
Reactions:
SMPDB Pathways:
Phenylalanine metabolismPW000921 Pw000921Pw000921 greyscalePw000921 simple
Secondary Metabolites: Histidine biosynthesisPW000984 Pw000984Pw000984 greyscalePw000984 simple
histidine biosynthesisPW000810 Pw000810Pw000810 greyscalePw000810 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-000t-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
References
References:
  • 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
  • AMES BN, HORECKER BL: The biosynthesis of histidine: imidazoleacetol phosphate transaminase. J Biol Chem. 1956 May;220(1):113-28. Pubmed: 13319331
  • 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
  • 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
  • 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
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16426
HMDB IDHMDB12236
Pubchem Compound ID792
Kegg IDC01267
ChemSpider ID770
Wikipedia IDNot Available
BioCyc IDIMIDAZOLE-ACETOL-P
EcoCyc IDIMIDAZOLE-ACETOL-P

Enzymes

General function:
Involved in transferase activity
Specific function:
L-histidinol phosphate + 2-oxoglutarate = 3- (imidazol-4-yl)-2-oxopropyl phosphate + L-glutamate
Gene Name:
hisC
Uniprot ID:
P06986
Molecular weight:
39360
Reactions
L-histidinol phosphate + 2-oxoglutarate = 3-(imidazol-4-yl)-2-oxopropyl phosphate + L-glutamate.
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.