2.0 2015-09-08 17:50:03 -0600 2016-09-13 16:35:43 -0600 ECMDB24201 M2MDB006318 1-(o-carboxyphenylamino)-1'-deoxyribulose 5'-phosphate 1-(o-Carboxyphenylamino)-1'-deoxyribulose 5'-phosphate is a pentose phosphate derivative. It is a substrate for indole-3-glycerol-phosphate synthase (IPGS) (EC 4.1.1.48)which is an enzyme that catalyzes the chemical reaction: 1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate ightleftharpoons 1-C-(indol-3-yl)-glycerol 3-phosphate + CO2 + H2O 1-(O-carboxyphenylamino)-1'-Deoxyribulose 5'-phosphoric acid 2-{[(3R,4R)-3,4-dihydroxy-2-oxo-5-(phosphonatooxy)pentyl]amino}benzoate 2-{[(3R,4R)-3,4-dihydroxy-2-oxo-5-(phosphonatooxy)pentyl]amino}benzoate logp -0.09 ALOGPS logs -1.42 ALOGPS solubility 1.51e+01 g/l ALOGPS logp -0.5 ChemAxon pka_strongest_acidic 1.48 ChemAxon pka_strongest_basic 0.27 ChemAxon iupac 2-{[(3R,4R)-3,4-dihydroxy-2-oxo-5-(phosphonatooxy)pentyl]amino}benzoate ChemAxon polar_surface_area 182.11 ChemAxon refractivity 86.31 ChemAxon polarizability 29.42 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 9 ChemAxon donor_count 3 ChemAxon physiological_charge -3 ChemAxon formal_charge -3 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 Specdb::MsMs 27389 Specdb::MsMs 27390 Specdb::MsMs 27391 Specdb::MsMs 33947 Specdb::MsMs 33948 Specdb::MsMs 33949 Tryptophan biosynthesis protein trpCF P00909 TRPC_ECOLI trpC http://ecmdb.ca/proteins/P00909.xml N-(5-phosphoribosyl)-anthranilate + N-(5-phosphoribosyl)-anthranilate > 1-(o-carboxyphenylamino)-1'-deoxyribulose 5'-phosphate + 1-(o-carboxyphenylamino)-1'-deoxyribulose 5'-phosphate PW_R002896 1-(o-carboxyphenylamino)-1'-deoxyribulose 5'-phosphate + Hydrogen ion + 1-(o-carboxyphenylamino)-1'-deoxyribulose 5'-phosphate > Water + Carbon dioxide PW_R002897 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