2.0 2015-09-08 17:50:02 -0600 2015-09-14 16:46:10 -0600 ECMDB24200 M2MDB006317 N-(5-phosphoribosyl)-anthranilate N-(5-Phosphoribosyl)-anthranilate is a member of the chemical class known as Pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. N-(5-phosphoribosyl)-anthranilate is invovled in tryptophan biosynthesis. N-(5'-Phosphoribosyl)anthranilate isomerase-indole-3-glycerol-phosphate synthase from Escherichia coli is a monomeric bifunctional enzyme of Mr 49,500 that catalyzes two sequential reactions in the biosynthesis of tryptophan. (PMID 3303031) Phosphoribosyl anthranilate isomerase from Thermotoga maritima is an extremely stable and active homodimer. (PMID 8897600) N-(5-Phosphoribosyl)-anthranilic acid C12H13NO9P 346.209 346.03443874 2-({3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}amino)benzoate 2-({3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}amino)benzoate OC1C(O)C(NC2=C(C=CC=C2)C([O-])=O)OC1COP([O-])([O-])=O InChI=1S/C12H16NO9P/c14-9-8(5-21-23(18,19)20)22-11(10(9)15)13-7-4-2-1-3-6(7)12(16)17/h1-4,8-11,13-15H,5H2,(H,16,17)(H2,18,19,20)/p-3 PMFMJXPRNJUYMB-UHFFFAOYSA-K logp 0.09 ALOGPS logs -1.27 ALOGPS solubility 2.15e+01 g/l ALOGPS logp -0.15 ChemAxon pka_strongest_acidic 1.23 ChemAxon pka_strongest_basic -2.1 ChemAxon iupac 2-({3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}amino)benzoate ChemAxon average_mass 346.209 ChemAxon mono_mass 346.03443874 ChemAxon smiles OC1C(O)C(NC2=C(C=CC=C2)C([O-])=O)OC1COP([O-])([O-])=O ChemAxon formula C12H13NO9P ChemAxon inchi InChI=1S/C12H16NO9P/c14-9-8(5-21-23(18,19)20)22-11(10(9)15)13-7-4-2-1-3-6(7)12(16)17/h1-4,8-11,13-15H,5H2,(H,16,17)(H2,18,19,20)/p-3 ChemAxon inchikey PMFMJXPRNJUYMB-UHFFFAOYSA-K ChemAxon polar_surface_area 174.27 ChemAxon refractivity 84.67 ChemAxon polarizability 29.01 ChemAxon rotatable_bond_count 6 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 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::NmrOneD 329142 Specdb::NmrOneD 329143 Specdb::NmrOneD 329144 Specdb::NmrOneD 329145 Specdb::NmrOneD 329146 Specdb::NmrOneD 329147 Specdb::NmrOneD 329148 Specdb::NmrOneD 329149 Specdb::NmrOneD 329150 Specdb::NmrOneD 329151 Specdb::NmrOneD 329152 Specdb::NmrOneD 329153 Specdb::NmrOneD 329154 Specdb::NmrOneD 329155 Specdb::NmrOneD 329156 Specdb::NmrOneD 329157 Specdb::NmrOneD 329158 Specdb::NmrOneD 329159 Specdb::NmrOneD 329160 Specdb::NmrOneD 329161 Specdb::MsMs 23768 Specdb::MsMs 23769 Specdb::MsMs 23770 Specdb::MsMs 30566 Specdb::MsMs 30567 Specdb::MsMs 30568 Anthranilate synthase component II P00904 TRPG_ECOLI trpD http://ecmdb.ca/proteins/P00904.xml Tryptophan biosynthesis protein trpCF P00909 TRPC_ECOLI trpC http://ecmdb.ca/proteins/P00909.xml 2-Aminobenzoic acid + Phosphoribosyl pyrophosphate > Pyrophosphate + N-(5-phosphoribosyl)-anthranilate + N-(5-phosphoribosyl)-anthranilate PW_R002895 N-(5-phosphoribosyl)-anthranilate + N-(5-phosphoribosyl)-anthranilate > 1-(o-carboxyphenylamino)-1'-deoxyribulose 5'-phosphate + 1-(o-carboxyphenylamino)-1'-deoxyribulose 5'-phosphate PW_R002896 N-(5-phosphoribosyl)-anthranilate + N-(5-phosphoribosyl)-anthranilate > 1-(2-Carboxyphenylamino)-1'-deoxyribulose-5'-phosphate PW_R005355