Record Information
Version2.0
Creation Date2012-05-31 14:21:05 -0600
Update Date2015-06-03 17:19:03 -0600
Secondary Accession Numbers
  • ECMDB12208
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
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
Weight:Average: 238.1351
Monoisotopic: 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
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
  • 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
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:
SMPDB Pathways:
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-MSsplash10-0002-9100000000-d7621780646907150961View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-3902000000-672dc9789ba9dac4f90bView in MoNA
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

Enzymes

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.
General function:
Involved in transferase activity, transferring pentosyl groups
Specific function:
IGPS catalyzes the conversion of PRFAR and glutamine to IGP, AICAR and glutamate. The hisH subunit provides the glutamine amidotransferase activity that produces the ammonia necessary to hisF for the synthesis of IGP and AICAR
Gene Name:
hisH
Uniprot ID:
P60595
Molecular weight:
21653
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 catalytic activity
Specific function:
IGPS catalyzes the conversion of PRFAR and glutamine to IGP, AICAR and glutamate. The hisF subunit catalyzes the cyclization activity that produces IGP and AICAR from PRFAR using the ammonia provided by the hisH subunit
Gene Name:
hisF
Uniprot ID:
P60664
Molecular weight:
28454
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.