2.0 2012-05-31 14:30:39 -0600 2015-06-03 17:19:26 -0600 ECMDB20160 M2MDB001007 Indoleglycerol phosphate 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) (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 C11H14NO6P 287.2057 287.055873697 [(2R,3S)-2,3-dihydroxy-3-(1H-indol-3-yl)propoxy]phosphonic acid indole-3-glycerol phosphate 4220-97-7 [H][C@@](O)(COP(O)(O)=O)[C@@]([H])(O)C1=CNC2=C1C=CC=C2 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 NQEQTYPJSIEPHW-MNOVXSKESA-N Cytosol logp -0.21 ALOGPS logs -1.87 ALOGPS solubility 3.87e+00 g/l ALOGPS logp -0.08 ChemAxon pka_strongest_acidic 1.49 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac [(2R,3S)-2,3-dihydroxy-3-(1H-indol-3-yl)propoxy]phosphonic acid ChemAxon average_mass 287.2057 ChemAxon mono_mass 287.055873697 ChemAxon smiles [H][C@@](O)(COP(O)(O)=O)[C@@]([H])(O)C1=CNC2=C1C=CC=C2 ChemAxon formula C11H14NO6P ChemAxon 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 ChemAxon inchikey NQEQTYPJSIEPHW-MNOVXSKESA-N ChemAxon polar_surface_area 123.01 ChemAxon refractivity 66.76 ChemAxon polarizability 25.41 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 5 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Phenylalanine, tyrosine and tryptophan biosynthesis ec00400 Glycine, serine and threonine metabolism ec00260 Metabolic pathways eco01100 tryptophan biosynthesis TRPSYN-PWY Specdb::CMs 3249 Specdb::NmrOneD 335738 Specdb::NmrOneD 335739 Specdb::NmrOneD 335740 Specdb::NmrOneD 335741 Specdb::NmrOneD 335742 Specdb::NmrOneD 335743 Specdb::NmrOneD 335744 Specdb::NmrOneD 335745 Specdb::NmrOneD 335746 Specdb::NmrOneD 335747 Specdb::NmrOneD 335748 Specdb::NmrOneD 335749 Specdb::NmrOneD 335750 Specdb::NmrOneD 335751 Specdb::NmrOneD 335752 Specdb::NmrOneD 335753 Specdb::NmrOneD 335754 Specdb::NmrOneD 335755 Specdb::NmrOneD 335756 Specdb::NmrOneD 335757 Specdb::MsMs 35576 Specdb::MsMs 35577 Specdb::MsMs 35578 Specdb::MsMs 3607624 Specdb::MsMs 3607625 Specdb::MsMs 3607626 Specdb::MsMs 29018 Specdb::MsMs 29019 Specdb::MsMs 29020 Specdb::MsMs 3607621 Specdb::MsMs 3607622 Specdb::MsMs 3607623 444150 C03506 18299 INDOLE-3-GLYCEROL-P IGP 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. 21097882 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. 22080510 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. 17765195 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. 15879705 Hommel, U., Eberhard, M., Kirschner, K. (1995). "Phosphoribosyl anthranilate isomerase catalyzes a reversible amadori reaction." Biochemistry 34:5429-5439. 7727401 Tryptophan biosynthesis protein trpCF P00909 TRPC_ECOLI trpC http://ecmdb.ca/proteins/P00909.xml Tryptophan synthase alpha chain P0A877 TRPA_ECOLI trpA http://ecmdb.ca/proteins/P0A877.xml Tryptophan synthase beta chain P0A879 TRPB_ECOLI trpB http://ecmdb.ca/proteins/P0A879.xml Indoleglycerol phosphate + L-Serine > D-Glyceraldehyde 3-phosphate + Water + L-Tryptophan R02722 TRYPSYN-RXN Indoleglycerol phosphate > D-Glyceraldehyde 3-phosphate + Indole R02340 RXN0-2381 1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate + Hydrogen ion <> Indoleglycerol phosphate + Carbon dioxide + Water R03508 IGPSYN-RXN Indoleglycerol phosphate <> Indole + D-Glyceraldehyde 3-phosphate R02340 L-Serine + Indoleglycerol phosphate <> L-Tryptophan + D-Glyceraldehyde 3-phosphate + Water R02722 1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate <> Indoleglycerol phosphate + Carbon dioxide + Water R03508 Hydrogen ion + 1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate > Indoleglycerol phosphate + Carbon dioxide + Water IGPSYN-RXN L-Serine + Indoleglycerol phosphate > L-Tryptophan + glyceraldehyde 3-phosphate + Water L-Serine + Indoleglycerol phosphate + Indole <> L-Tryptophan + D-Glyceraldehyde 3-phosphate + Water R02722 1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate + Hydrogen ion <> Indoleglycerol phosphate + Carbon dioxide + Water