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Record Information
Version	2.0
Creation Date	2012-05-31 14:21:05 -0600
Update Date	2015-06-03 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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xae95e1d4> Close
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
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 Secondary alcohols 1,2-diols Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Aromatic alcohols
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 Framework	Aromatic heteromonocyclic compounds
External Descriptors	imidazoles (CHEBI:17805 ) sn-glycerol 3-phosphates (CHEBI:17805 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 22.2 g/L ALOGPS logP -1.6 ALOGPS logP -4.3 ChemAxon logS -1 ALOGPS pKa (Strongest Acidic) 1.48 ChemAxon pKa (Strongest Basic) 5.79 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 135.9 Ų ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 48.18 m³·mol⁻¹ ChemAxon Polarizability 19.79 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-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 D-Erythro-imidazole-glycerol-phosphate > Imidazole acetol-phosphate + Water Phosphoribulosylformimino-AICAR-P + L-Glutamine > L-Glutamic acid + Hydrogen ion + 5-Amino-4-imidazolecarboxyamide + D-Erythro-imidazole-glycerol-phosphate + L-Glutamate
SMPDB Pathways:	Secondary Metabolites: Histidine biosynthesis PW000984 histidine biosynthesis PW000810
KEGG Pathways:	Histidine metabolism ec00340
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 splash10-0002-9100000000-d7621780646907150961 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive splash10-014i-3902000000-672dc9789ba9dac4f90b View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer 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 splash10-000i-1590000000-995459a9c601e4f93bb9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-01bm-7930000000-7a1fc0321a5a26cb3641 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-014i-9100000000-233300ba036335dbdb36 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-002s-9160000000-586419351fea64eb6eaa View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9000000000-4b73b23e7fb5e36e8b12 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-3234231a277bb5d275a3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0076-0930000000-9d0199b4a40acd09d950 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00dl-6900000000-61cc16ade0d5022d7ba7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-014i-9000000000-5ce5f6fd52eba0bf6485 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-002s-9070000000-6f235e806e9d50bbef56 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9000000000-773be54506d41c124bd4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-7800232852d6f8ad7663 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:	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
Links
External Links:	Resource Link CHEBI ID 17805 HMDB ID HMDB12208 Pubchem Compound ID 440431 Kegg ID C04666 ChemSpider ID 389372 Wikipedia ID Not Available BioCyc ID D-ERYTHRO-IMIDAZOLE-GLYCEROL-P EcoCyc ID D-ERYTHRO-IMIDAZOLE-GLYCEROL-P

Enzymes