2.0 2015-09-08 17:50:03 -0600 2015-09-14 16:46:09 -0600 ECMDB24202 M2MDB006319 (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate (1S,2R)-1-C-(indol-3-yl)glycerol 3-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. (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate is involved in tryptophan biosynthesis. The latter is the competent substrate of (1S,2R)-1-C-(indol-3-yl)glycerol 3-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-phosphoric acid C11H12NO6P 285.193 285.041321268 1-(1H-indol-3-yl)-3-(phosphonatooxy)propane-1,2-diol 1-(1H-indol-3-yl)-3-(phosphonatooxy)propane-1,2-diol OC(COP([O-])([O-])=O)C(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)/p-2 NQEQTYPJSIEPHW-UHFFFAOYSA-L logp 0.12 ALOGPS logs -1.19 ALOGPS solubility 2.05e+01 g/l ALOGPS logp -0.08 ChemAxon pka_strongest_acidic 1.49 ChemAxon pka_strongest_basic -3.4 ChemAxon iupac 1-(1H-indol-3-yl)-3-(phosphonatooxy)propane-1,2-diol ChemAxon average_mass 285.193 ChemAxon mono_mass 285.041321268 ChemAxon smiles OC(COP([O-])([O-])=O)C(O)C1=CNC2=C1C=CC=C2 ChemAxon formula C11H12NO6P 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)/p-2 ChemAxon inchikey NQEQTYPJSIEPHW-UHFFFAOYSA-L ChemAxon polar_surface_area 128.67 ChemAxon refractivity 64.51 ChemAxon polarizability 25.52 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge -2 ChemAxon Tryptophan metabolism The biosynthesis of L-tryptophan begins with L-glutamine interacting with a chorismate through a anthranilate synthase which results in a L-glutamic acid, a pyruvic acid, a hydrogen ion and a 2-aminobenzoic acid. The aminobenzoic acid interacts with a phosphoribosyl pyrophosphate through an anthranilate synthase component II resulting in a pyrophosphate and a N-(5-phosphoribosyl)-anthranilate. The latter compound is then metabolized by an indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in a 1-(o-carboxyphenylamino)-1-deoxyribulose 5'-phosphate. This compound then interacts with a hydrogen ion through a indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in the release of carbon dioxide, a water molecule and a (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate. The latter compound then interacts with a D-glyceraldehyde 3-phosphate and an Indole. The indole interacts with an L-serine through a tryptophan synthase, β subunit dimer resulting in a water molecule and an L-tryptophan. The metabolism of L-tryptophan starts with L-tryptophan being dehydrogenated by a tryptophanase / L-cysteine desulfhydrase resulting in the release of a hydrogen ion, an Indole and a 2-aminoacrylic acid. The latter compound is isomerized into a 2-iminopropanoate. This compound then interacts with a water molecule and a hydrogen ion spontaneously resulting in the release of an Ammonium and a pyruvic acid. The pyruvic acid then interacts with a coenzyme A through a NAD driven pyruvate dehydrogenase complex resulting in the release of a NADH, a carbon dioxide and an Acetyl-CoA PW000815 ec00380 Metabolic tryptophan metabolism II The biosynthesis of L-tryptophan begins with L-glutamine interacting with a chorismate through a anthranilate synthase which results in a L-glutamic acid, a pyruvic acid, a hydrogen ion and a 2-aminobenzoic acid. The aminobenzoic acid interacts with a phosphoribosyl pyrophosphate through an anthranilate synthase component II resulting in a pyrophosphate and a N-(5-phosphoribosyl)-anthranilate. The latter compound is then metabolized by an indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in a 1-(o-carboxyphenylamino)-1-deoxyribulose 5'-phosphate. This compound then interacts with a hydrogen ion through a indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in the release of carbon dioxide, a water molecule and a (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate. The latter compound then interacts with a D-glyceraldehyde 3-phosphate and an Indole. The indole interacts with an L-serine through a tryptophan synthase, β subunit dimer resulting in a water molecule and an L-tryptophan. The metabolism of L-tryptophan starts with L-tryptophan being dehydrogenated by a tryptophanase / L-cysteine desulfhydrase resulting in the release of a hydrogen ion, an Indole and a 2-aminoacrylic acid. The latter compound is isomerized into a 2-iminopropanoate. This compound then interacts with a water molecule and a hydrogen ion spontaneously resulting in the release of an Ammonium and a pyruvic acid. The pyruvic acid then interacts with a coenzyme A through a NAD driven pyruvate dehydrogenase complex resulting in the release of a NADH, a carbon dioxide and an Acetyl-CoA PW001916 Metabolic Specdb::MsMs 26582 Specdb::MsMs 26583 Specdb::MsMs 26584 Specdb::MsMs 33140 Specdb::MsMs 33141 Specdb::MsMs 33142 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 1-(o-carboxyphenylamino)-1'-deoxyribulose 5'-phosphate + Hydrogen ion + 1-(o-carboxyphenylamino)-1'-deoxyribulose 5'-phosphate > Water + Carbon dioxide + (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate PW_R002898 1-(2-Carboxyphenylamino)-1'-deoxyribulose-5'-phosphate + Hydrogen ion > Carbon dioxide + Water + (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate PW_R005357 (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate > D-Glyceraldehyde 3-phosphate + Indole + D-Glyceraldehyde 3-phosphate PW_R002899