2.02012-05-31 14:30:39 -06002015-06-03 17:19:26 -0600ECMDB20160M2MDB001007Indoleglycerol phosphateIndoleglycerol 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)(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 acid1-(Indol-3-yl)glycerol-3-P1-(Indol-3-yl)glycerol-3-phosphate1-(indol-3-yl)Glycerol-3-phosphoric acid1-C-(Indol-3-yl)glycerol 3-phosphate1-C-(indol-3-yl)Glycerol 3-phosphoric acidC1-(3-Indolyl)-glycerol 3-phosphateC1-(3-Indolyl)-glycerol 3-phosphoric acidC<sup>1</sup>-(3-Indolyl)-glycerol 3-phosphateIG-PIGPIndole-3-glycerol phosphateIndole-3-glycerol phosphoric acidIndole-3-glycerol-PIndole-3-glycerol-phosphateIndole-3-glycerol-phosphoric acidIndoleglycerol phosphateIndoleglycerol phosphoric acidC11H14NO6P287.2057287.055873697[(2R,3S)-2,3-dihydroxy-3-(1H-indol-3-yl)propoxy]phosphonic acidindole-3-glycerol phosphate4220-97-7[H][C@@](O)(COP(O)(O)=O)[C@@]([H])(O)C1=CNC2=C1C=CC=C2InChI=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/s1NQEQTYPJSIEPHW-MNOVXSKESA-NCytosollogp-0.21logs-1.87solubility3.87e+00 g/llogp-0.08pka_strongest_acidic1.49pka_strongest_basic-3.4iupac[(2R,3S)-2,3-dihydroxy-3-(1H-indol-3-yl)propoxy]phosphonic acidaverage_mass287.2057mono_mass287.055873697smiles[H][C@@](O)(COP(O)(O)=O)[C@@]([H])(O)C1=CNC2=C1C=CC=C2formulaC11H14NO6PinchiInChI=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/s1inchikeyNQEQTYPJSIEPHW-MNOVXSKESA-Npolar_surface_area123.01refractivity66.76polarizability25.41rotatable_bond_count5acceptor_count5donor_count5physiological_charge-2formal_charge0Phenylalanine, tyrosine and tryptophan biosynthesisec00400Glycine, serine and threonine metabolismec00260Metabolic pathwayseco01100tryptophan biosynthesisTRPSYN-PWYSpecdb::CMs3249Specdb::NmrOneD335738Specdb::NmrOneD335739Specdb::NmrOneD335740Specdb::NmrOneD335741Specdb::NmrOneD335742Specdb::NmrOneD335743Specdb::NmrOneD335744Specdb::NmrOneD335745Specdb::NmrOneD335746Specdb::NmrOneD335747Specdb::NmrOneD335748Specdb::NmrOneD335749Specdb::NmrOneD335750Specdb::NmrOneD335751Specdb::NmrOneD335752Specdb::NmrOneD335753Specdb::NmrOneD335754Specdb::NmrOneD335755Specdb::NmrOneD335756Specdb::NmrOneD335757Specdb::MsMs35576Specdb::MsMs35577Specdb::MsMs35578Specdb::MsMs3607624Specdb::MsMs3607625Specdb::MsMs3607626Specdb::MsMs29018Specdb::MsMs29019Specdb::MsMs29020Specdb::MsMs3607621Specdb::MsMs3607622Specdb::MsMs3607623444150C0350618299INDOLE-3-GLYCEROL-PIGPKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510van 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 370:17-25.17765195Jeong, 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 19:219-222.15879705Hommel, U., Eberhard, M., Kirschner, K. (1995). "Phosphoribosyl anthranilate isomerase catalyzes a reversible amadori reaction." Biochemistry 34:5429-5439.7727401Tryptophan biosynthesis protein trpCFP00909TRPC_ECOLItrpChttp://ecmdb.ca/proteins/P00909.xmlTryptophan synthase alpha chainP0A877TRPA_ECOLItrpAhttp://ecmdb.ca/proteins/P0A877.xmlTryptophan synthase beta chainP0A879TRPB_ECOLItrpBhttp://ecmdb.ca/proteins/P0A879.xmlIndoleglycerol phosphate + L-Serine > D-Glyceraldehyde 3-phosphate + Water + L-TryptophanR02722TRYPSYN-RXNIndoleglycerol phosphate > D-Glyceraldehyde 3-phosphate + IndoleR02340RXN0-23811-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate + Hydrogen ion <> Indoleglycerol phosphate + Carbon dioxide + WaterR03508IGPSYN-RXNIndoleglycerol phosphate <> Indole + D-Glyceraldehyde 3-phosphateR02340L-Serine + Indoleglycerol phosphate <> L-Tryptophan + D-Glyceraldehyde 3-phosphate + WaterR027221-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate <> Indoleglycerol phosphate + Carbon dioxide + WaterR03508Hydrogen ion + 1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate > Indoleglycerol phosphate + Carbon dioxide + WaterIGPSYN-RXNL-Serine + Indoleglycerol phosphate > L-Tryptophan + glyceraldehyde 3-phosphate + WaterL-Serine + Indoleglycerol phosphate + Indole <> L-Tryptophan + D-Glyceraldehyde 3-phosphate + WaterR02722 1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate + Hydrogen ion <> Indoleglycerol phosphate + Carbon dioxide + Water