D-Erythro-imidazole-glycerol-phosphate (PAMDB000829)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000829
Identification
Name: D-Erythro-imidazole-glycerol-phosphate
Description:D-Erythro-imidazole-glycerol-phosphate is an intermediate in Histidine metabolism. It is a substrate for imidazoleglycerol-phosphate dehydratase (hisB) and can be generated from Phosphoribulosyl-formimino-AICAR-phosphate then it is converted to Imidazole-acetol phosphate.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • D-Erythro-1-(imidazol-4-yl)-glycerol-3-phosphate
  • D-erythro-1-(Imidazol-4-yl)-glycerol-3-phosphoric acid
  • D-Erythro-1-(Imidazol-4-yl)glycerol 3-phosphate
  • D-erythro-1-(Imidazol-4-yl)glycerol 3-phosphoric acid
  • D-Erythro-Imidazole-glycerol 3-phosphate
  • D-erythro-Imidazole-glycerol 3-phosphoric acid
  • D-Erythro-imidazole-glycerol phosphate
  • D-erythro-Imidazole-glycerol phosphoric acid
  • D-erythro-imidazole-glycerol-P
  • D-erythro-Imidazole-glycerol-phosphoric acid
  • D-Erythro-imidazoleglycerol-phosphate
  • D-erythro-Imidazoleglycerol-phosphoric acid
  • EIGP
  • Erythro-imidazole-glycerol-P
  • Erythro-imidazole-glycerol-phosphate
  • erythro-Imidazole-glycerol-phosphoric acid
  • IGP
  • Imidazole glycerol phosphate
  • Imidazole glycerol phosphoric acid
Chemical Formula: C6H11N2O6P
Average Molecular Weight: 238.1351
Monoisotopic Molecular Weight: 238.035472606
InChI Key: HFYBTHCYPKEDQQ-RITPCOANSA-N
InChI:InChI=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
CAS number: 36244-87-8
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
SMILES:O[C@H](COP(O)(O)=O)[C@@H](O)C1=CNC=N1
Chemical Taxonomy
Taxonomy DescriptionThis compound 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 ClassOrganophosphorus compounds
Class Organic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct Parent Monoalkyl phosphates
Alternative Parents
Substituents
  • Monoalkyl phosphate
  • Organic phosphate
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility22.2 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity48.18 m3·mol-1ChemAxon
Polarizability19.79 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
L-Glutamine + Phosphoribulosylformimino-AICAR-P > Phosphoribosyl formamidocarboxamide + D-Erythro-imidazole-glycerol-phosphate + L-Glutamate + Hydrogen ion
D-Erythro-imidazole-glycerol-phosphate <> Water + Imidazole acetol-phosphate
Phosphoribulosylformimino-AICAR-P + L-Glutamine <> D-Erythro-imidazole-glycerol-phosphate + AICAR + L-Glutamate
Phosphoribulosylformimino-AICAR-P + L-Glutamine > Hydrogen ion + L-Glutamate + D-Erythro-imidazole-glycerol-phosphate + AICAR
Phosphoribulosylformimino-AICAR-P + L-Glutamine > L-Glutamic acid + Hydrogen ion + 5-Amino-4-imidazolecarboxyamide + D-Erythro-imidazole-glycerol-phosphate + L-Glutamate
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1590000000-995459a9c601e4f93bb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01bm-7930000000-7a1fc0321a5a26cb3641View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-233300ba036335dbdb36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002s-9160000000-586419351fea64eb6eaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-4b73b23e7fb5e36e8b12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-3234231a277bb5d275a3View in MoNA
References
References:
  • 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
  • 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 ID17805
HMDB IDHMDB12208
Pubchem Compound ID440431
Kegg IDC04666
ChemSpider ID389372
Wikipedia IDNot Available
BioCyc IDD-ERYTHRO-IMIDAZOLE-GLYCEROL-P
EcoCyc IDD-ERYTHRO-IMIDAZOLE-GLYCEROL-P