Indoleglycerol phosphate (PAMDB001007)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001007
Identification
Name: Indoleglycerol phosphate
Description:Indoleglycerol phosphate is a member of the chemical class known as Indoles. These are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. Indoleglycerol phosphate is involved in tryptophan biosynthesis. The latter is the competent substrate of indoleglycerol phosphate synthase, which catalyzes the subsequent step of tryptophan biosynthesis. (PMID 7727401) alphaTS by itself catalyzes the cleavage of indole-3-glycerol phosphate to glyceraldehyde-3-phosphate and indole, which is converted to tryptophan in tryptophan biosynthesis. (PMID 15879705)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (1S,2R)-1-C-(Indol-3-yl)glycerol 3-phosphate
  • (1S,2R)-1-C-(indol-3-yl)Glycerol 3-phosphoric acid
  • (3-Indolyl)-glycerol phosphate
  • (3-Indolyl)-glycerol phosphoric acid
  • 1-(Indol-3-yl)glycerol-3-P
  • 1-(Indol-3-yl)glycerol-3-phosphate
  • 1-(indol-3-yl)Glycerol-3-phosphoric acid
  • 1-C-(Indol-3-yl)glycerol 3-phosphate
  • 1-C-(indol-3-yl)Glycerol 3-phosphoric acid
  • C1-(3-Indolyl)-glycerol 3-phosphate
  • C1-(3-Indolyl)-glycerol 3-phosphoric acid
  • C1-(3-Indolyl)-glycerol 3-phosphate
  • IG-P
  • IGP
  • Indole-3-glycerol phosphate
  • Indole-3-glycerol phosphoric acid
  • Indole-3-glycerol-P
  • Indole-3-glycerol-phosphate
  • Indole-3-glycerol-phosphoric acid
  • Indoleglycerol phosphate
  • Indoleglycerol phosphoric acid
Chemical Formula: C11H14NO6P
Average Molecular Weight: 287.2057
Monoisotopic Molecular Weight: 287.055873697
InChI Key: NQEQTYPJSIEPHW-MNOVXSKESA-N
InChI:InChI=1S/C11H14NO6P/c13-10(6-18-19(15,16)17)11(14)8-5-12-9-4-2-1-3-7(8)9/h1-5,10-14H,6H2,(H2,15,16,17)/t10-,11+/m1/s1
CAS number: 4220-97-7
IUPAC Name:[(2R,3S)-2,3-dihydroxy-3-(1H-indol-3-yl)propoxy]phosphonic acid
Traditional IUPAC Name: indole-3-glycerol phosphate
SMILES:[H][C@@](O)(COP(O)(O)=O)[C@@]([H])(O)C1=CNC2=C1C=CC=C2
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as indoles. These are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Indoles and derivatives
Sub ClassIndoles
Direct Parent Indoles
Alternative Parents
Substituents
  • Indole
  • Monoalkyl phosphate
  • Benzenoid
  • Alkyl phosphate
  • Substituted pyrrole
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Heteroaromatic compound
  • Pyrrole
  • Secondary alcohol
  • 1,2-diol
  • Azacycle
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility3.87 mg/mLALOGPS
logP-0.21ALOGPS
logP-0.08ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.49ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area123.01 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity66.76 m3·mol-1ChemAxon
Polarizability25.41 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Indoleglycerol phosphate + L-Serine > D-Glyceraldehyde 3-phosphate + Water + L-Tryptophan
Indoleglycerol phosphate > D-Glyceraldehyde 3-phosphate + Indole
1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate + Hydrogen ion <> Indoleglycerol phosphate + Carbon dioxide + Water
1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate <> Indoleglycerol phosphate + Carbon dioxide + Water
L-Serine + Indoleglycerol phosphate > L-Tryptophan + glyceraldehyde 3-phosphate + Water
L-Serine + Indoleglycerol phosphate + Indole <> L-Tryptophan + D-Glyceraldehyde 3-phosphate + Water
Pathways:
  • Glycine, serine and threonine metabolism pae00260
  • Metabolic pathways pae01100
  • Phenylalanine, tyrosine and tryptophan biosynthesis pae00400
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-1890000000-61a462086b1984fd95ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00r5-2920000000-9a1b057494b6f12812d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-2900000000-0273b8f673c7daddc7caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-6390000000-f17b5507f97353c5dbf8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-935793bf974f83d59858View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-c0a8c6db2c733f0ed5e0View in MoNA
References
References:
  • Hommel, U., Eberhard, M., Kirschner, K. (1995). "Phosphoribosyl anthranilate isomerase catalyzes a reversible amadori reaction." Biochemistry 34:5429-5439. Pubmed: 7727401
  • Jeong, M. S., Jang, S. B. (2005). "Crystallization and X-ray crystallographic studies of wild-type and mutant tryptophan synthase alpha-subunits from Escherichia coli." Mol Cells 19:219-222. Pubmed: 15879705
  • 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 ID18299
HMDB IDNot Available
Pubchem Compound ID444150
Kegg IDC03506
ChemSpider ID392148
Wikipedia IDNot Available
BioCyc IDINDOLE-3-GLYCEROL-P
EcoCyc IDINDOLE-3-GLYCEROL-P
Ligand ExpoIGP