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Imidazole acetol-phosphate (YMDB00070)

Identification
YMDB IDYMDB00070
NameImidazole acetol-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionImidazole acetol-phosphate 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. Imidazole acetol-phosphate exists in all living species, ranging from bacteria to plants to humans. In yeast, imidazole acetol-phosphate is involved in the metabolic pathway called the histidine biosynthesis pathway. Based on a literature review a small amount of articles have been published on Imidazole acetol-phosphate.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • 1-(1H-imidazol-4-yl)-3-(phosphonooxy)-2-propanone
  • 3-(1H-imidazol-4-yl)-2-oxopropyl dihydrogen phosphate
  • 3-(imidazol-4-yl)-2-oxopropyl dihydrogen phosphate
  • 3-(Imidazol-4-yl)-2-oxopropyl phosphate
  • Imidazole acetol phosphate
  • Imidazole acetol-p
  • Imidazole-acetol phosphate
  • 3-(Imidazol-4-yl)-2-oxopropyl phosphoric acid
  • Imidazole-acetol phosphoric acid
  • Imidazole acetol-phosphoric acid
  • 1-(1H-Imidazol-5-yl)-3-(phosphonooxy)-2-propanone
CAS number99979-59-6
WeightAverage: 220.1198
Monoisotopic: 220.02490792
InChI KeyYCFFMSOLUMRAMD-UHFFFAOYSA-N
InChIInChI=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)
IUPAC Name[3-(1H-imidazol-4-yl)-2-oxopropoxy]phosphonic acid
Traditional IUPAC Name3-(1H-imidazol-4-yl)-2-oxopropoxyphosphonic acid
Chemical FormulaC6H9N2O5P
SMILES[H]OP(=O)(O[H])OC([H])([H])C(=O)C([H])([H])C1=C([H])N([H])C([H])=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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Histidine BiosynthesisPW002418 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Histidine metabolismec00340 Map00340
SMPDB Reactions
D-Erythro-imidazole-glycerol-phosphate → water + Imidazole acetol-phosphate
Imidazole acetol-phosphate + L-Glutamic acid → Oxoglutaric acid + L-histidinol phosphate
KEGG Reactions
Imidazole acetol-phosphate + L-Glutamic acid → L-histidinol phosphate + Oxoglutaric acid
D-Erythro-imidazole-glycerol-phosphate → Imidazole acetol-phosphate + water
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-9200000000-41a681dee161ad4f3e7bJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-3390000000-102fb9b517f2001e0996JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kmi-4950000000-076be23324f875b841dcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9500000000-99bd6a8eac665bc00868JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-7190000000-c52bfb05c2cd90023536JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-7598c15214a6b2b67038JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-59a5e26dad504ee2412dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-199895f882e036c55087JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-3930000000-3a2cf619e974119e8f24JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pw9-9300000000-f31212a9e65f18dabcb3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2090000000-bd2937021ad7bda9fa53JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9020000000-af7370fa1a56f74a6fb4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-8c5fbfcdabecdcd6d55bJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16426
HMDB IDHMDB12236
Pubchem Compound ID792
Kegg IDC01267
ChemSpider ID770
FOODB IDFDB028879
Wikipedia IDNot Available
BioCyc IDIMIDAZOLE-ACETOL-P

Enzymes

Protein Details
1. Histidinol-phosphate aminotransferase
General function:
Involved in transferase activity
Specific function:
L-histidinol phosphate + 2-oxoglutarate = 3- (imidazol-4-yl)-2-oxopropyl phosphate + L-glutamate
Gene Name:
HIS5
Uniprot ID:
P07172
Molecular weight:
42645.69922
Reactions
L-histidinol phosphate + 2-oxoglutarate → 3-(imidazol-4-yl)-2-oxopropyl phosphate + L-glutamate.
Protein Details
2. Imidazoleglycerol-phosphate dehydratase
General function:
Involved in imidazoleglycerol-phosphate dehydratase activity
Specific function:
D-erythro-1-(imidazol-4-yl)glycerol 3- phosphate = 3-(imidazol-4-yl)-2-oxopropyl phosphate + H(2)O
Gene Name:
HIS3
Uniprot ID:
P06633
Molecular weight:
23833.0
Reactions
D-erythro-1-(imidazol-4-yl)glycerol 3-phosphate → 3-(imidazol-4-yl)-2-oxopropyl phosphate + H(2)O.