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Identification
YMDB IDYMDB00089
NameD-Erythro-imidazole-glycerol-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-Erythro-imidazole-glycerol-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. D-Erythro-imidazole-glycerol-phosphate is a very strong basic compound (based on its pKa). D-Erythro-imidazole-glycerol-phosphate exists in all living species, ranging from bacteria to humans. Within yeast, D-erythro-imidazole-glycerol-phosphate participates in a number of enzymatic reactions. In particular, L-glutamic acid, AICAR, and D-erythro-imidazole-glycerol-phosphate can be biosynthesized from phosphoribulosylformimino-aicar-p and L-glutamine; which is catalyzed by the enzyme imidazole glycerol phosphate synthase hishf. In addition, D-erythro-imidazole-glycerol-phosphate can be converted into imidazole acetol-phosphate through the action of the enzyme imidazole glycerol-phosphate dehydratase. In yeast, D-erythro-imidazole-glycerol-phosphate is involved in the metabolic pathway called histidine biosynthesis pathway.
Structure
Thumb
Synonyms
  • D-erythro-1-(Imidazol-4-yl)glycerol 3-phosphate
  • D-erythro-Imidazole-glycerol 3-phosphate
  • D-erythro-imidazole-glycerol phosphate
  • D-erythro-imidazoleglycerol-phosphate
  • D-Erythro-imidazole-glycerol 3-phosphoric acid
  • D-Erythro-imidazole-glycerol phosphoric acid
  • D-Erythro-imidazole-glycerol-phosphoric acid
CAS number36244-87-8
WeightAverage: 238.1351
Monoisotopic: 238.035472606
InChI KeyHFYBTHCYPKEDQQ-RITPCOANSA-N
InChIInChI=1S/C6H11N2O6P/c9-5(2-14-15(11,12)13)6(10)4-1-7-3-8-4/h1,3,5-6,9-10H,2H2,(H,7,8)(H2,11,12,13)/t5-,6+/m1/s1
IUPAC Name[(2R,3S)-2,3-dihydroxy-3-(1H-imidazol-4-yl)propoxy]phosphonic acid
Traditional IUPAC Name(2R,3S)-2,3-dihydroxy-3-(1H-imidazol-4-yl)propoxyphosphonic acid
Chemical FormulaC6H11N2O6P
SMILES[H]O[C@@]([H])(C1=C([H])N([H])C([H])=N1)[C@]([H])(O[H])C([H])([H])OP(=O)(O[H])O[H]
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
  • Secondary alcohol
  • 1,2-diol
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • 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 Solubility22.2 g/LALOGPS
logP-1.6ALOGPS
logP-4.3ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)1.48ChemAxon
pKa (Strongest Basic)5.79ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area135.9 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity48.18 m³·mol⁻¹ChemAxon
Polarizability19.79 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
Phosphoribulosylformimino-AICAR-P + L-GlutamineL-Glutamic acid + hydron + 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide + D-Erythro-imidazole-glycerol-phosphate
D-Erythro-imidazole-glycerol-phosphatewater + Imidazole acetol-phosphate
KEGG Reactions
5-[(5-phospho-1-deoxy-D-ribulos-1-ylimino)methylamino]-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide + L-Glutamine5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide + L-Glutamic acid + hydron + D-Erythro-imidazole-glycerol-phosphate
D-Erythro-imidazole-glycerol-phosphateImidazole 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, Positivesplash10-0002-9100000000-d7621780646907150961JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-014i-3902000000-672dc9789ba9dac4f90bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1590000000-995459a9c601e4f93bb9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01bm-7930000000-7a1fc0321a5a26cb3641JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-233300ba036335dbdb36JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002s-9160000000-586419351fea64eb6eaaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-4b73b23e7fb5e36e8b12JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-3234231a277bb5d275a3JSpectraViewer
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 ID17805
HMDB IDHMDB12208
Pubchem Compound ID440431
Kegg IDC04666
ChemSpider ID24785682
FOODB IDFDB028853
Wikipedia IDNot Available
BioCyc IDD-ERYTHRO-IMIDAZOLE-GLYCEROL-P

Enzymes

General function:
Involved in catalytic activity
Specific function:
IGPS catalyzes the conversion of PRFAR and glutamine to IGP, AICAR and glutamate. The glutamine amidotransferase domain provides the ammonia necessary to the cyclase domain to produce IGP and AICAR from PRFAR
Gene Name:
HIS7
Uniprot ID:
P33734
Molecular weight:
61067.60156
Reactions
5-[(5-phospho-1-deoxyribulos-1-ylamino)methylideneamino]-1-(5-phosphoribosyl)imidazole-4-carboxamide + L-glutamine → imidazole-glycerol phosphate + 5-aminoimidazol-4-carboxamide ribonucleotide + L-glutamate + H(2)O.
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.