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Record Information
Version	2.0
Creation Date	2012-05-31 14:21:11 -0600
Update Date	2015-06-03 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	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xafcb1844> Close
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
Description	belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Organic phosphoric acids and derivatives
Sub Class	Phosphate esters
Direct Parent	Monoalkyl phosphates
Alternative Parents	Imidazoles Heteroaromatic compounds Ketones Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
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	imidazoles (CHEBI:16426 ) oxoalkyl phosphate (CHEBI:16426 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 14.9 g/L ALOGPS logP -0.9 ALOGPS logP -3 ChemAxon logS -1.2 ALOGPS pKa (Strongest Acidic) 1.23 ChemAxon pKa (Strongest Basic) 6.65 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 112.51 Ų ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 46.07 m³·mol⁻¹ ChemAxon Polarizability 18.15 ų 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:	L-Glutamate + Imidazole acetol-phosphate <> alpha-Ketoglutarate + Histidinol phosphate D-Erythro-imidazole-glycerol-phosphate <> Water + Imidazole acetol-phosphate Histidinol phosphate + alpha-Ketoglutarate <> Imidazole acetol-phosphate + L-Glutamate Imidazole acetol-phosphate + L-Glutamate <> Histidinol phosphate + Oxoglutaric acid D-Erythro-imidazole-glycerol-phosphate > Imidazole acetol-phosphate + Water Histidinol phosphate + Oxoglutaric acid > Imidazole acetol-phosphate + L-Glutamate Imidazole acetol-phosphate + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + L-histidinol-phosphate
SMPDB Pathways:	Phenylalanine metabolism PW000921 Secondary Metabolites: Histidine biosynthesis PW000984 histidine biosynthesis PW000810
KEGG Pathways:	Histidine metabolism ec00340 Metabolic pathways eco01100 Novobiocin biosynthesis ec00401 Phenylalanine metabolism ec00360 Phenylalanine, tyrosine and tryptophan biosynthesis ec00400 Tropane, piperidine and pyridine alkaloid biosynthesis ec00960 Tyrosine metabolism ec00350
EcoCyc Pathways:	histidine biosynthesis HISTSYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-000t-9200000000-41a681dee161ad4f3e7b View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0fk9-3390000000-102fb9b517f2001e0996 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0kmi-4950000000-076be23324f875b841dc View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a59-9500000000-99bd6a8eac665bc00868 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-016r-7190000000-c52bfb05c2cd90023536 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9000000000-7598c15214a6b2b67038 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-59a5e26dad504ee2412d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00di-0090000000-199895f882e036c55087 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00di-3930000000-3a2cf619e974119e8f24 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0pw9-9300000000-f31212a9e65f18dabcb3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-014i-2090000000-bd2937021ad7bda9fa53 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9020000000-af7370fa1a56f74a6fb4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-8c5fbfcdabecdcd6d55b View in MoNA 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 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer
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
Links
External Links:	Resource Link CHEBI ID 16426 HMDB ID HMDB12236 Pubchem Compound ID 792 Kegg ID C01267 ChemSpider ID 770 Wikipedia ID Not Available BioCyc ID IMIDAZOLE-ACETOL-P EcoCyc ID IMIDAZOLE-ACETOL-P

Enzymes