2.0 2012-05-31 14:31:26 -0600 2015-06-03 17:19:27 -0600 ECMDB20174 M2MDB001021 N-(5-Phospho-D-ribosyl)anthranilate N-(5-phospho-D-ribosyl)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-Phospho-D-ribosyl)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) 5'-P-Ribosyl-anthranilate 5'-P-Ribosyl-anthranilic acid 5'-Phosphoribosyl-anthranilate 5'-Phosphoribosyl-anthranilic acid 5-P-Ribosyl-anthranilate 5-P-Ribosyl-anthranilic acid 5-Phosphoribosyl-anthranilate 5-Phosphoribosyl-anthranilic acid N-(5-phospho-β-D-ribosyl)-anthranilate N-(5-phospho-D-ribosyl)-anthranilate N-(5-phosphoribosyl)-anthranilate N-(5'-Phosphoribosyl)anthranilate N-(5'-Phosphoribosyl)anthranilic acid n-(5-phospho-β-D-ribosyl)-anthranilate n-(5-phospho-β-D-ribosyl)-anthranilic acid N-(5-phospho-b-D-Ribosyl)-anthranilate N-(5-phospho-b-D-Ribosyl)-anthranilic acid N-(5-phospho-b-D-Ribosyl)anthranilate N-(5-phospho-b-D-Ribosyl)anthranilic acid N-(5-Phospho-beta-D-ribosyl)-anthranilate N-(5-Phospho-beta-D-ribosyl)-anthranilic acid N-(5-Phospho-beta-D-ribosyl)anthranilate N-(5-Phospho-beta-D-ribosyl)anthranilic acid N-(5-Phospho-D-ribosyl)-anthranilate N-(5-Phospho-D-ribosyl)-anthranilic acid N-(5-Phospho-D-ribosyl)anthranilic acid N-(5-phospho-β-D-Ribosyl)-anthranilate N-(5-phospho-β-D-Ribosyl)-anthranilic acid N-(5-phospho-β-D-Ribosyl)anthranilate N-(5-phospho-β-D-Ribosyl)anthranilic acid N-(5-Phosphoribosyl)-anthranilate N-(5-Phosphoribosyl)-anthranilic acid N-(5-Phosphoribosyl)anthranilate N-(5-Phosphoribosyl)anthranilic acid Nprat PRAnth C12H16NO9P 349.2305 349.056267627 2-{[(3R,4S,5S)-3,4-dihydroxy-5-[hydroxy(phosphono)methyl]oxolan-2-yl]amino}benzoic acid 2-{[(3R,4S,5S)-3,4-dihydroxy-5-[hydroxy(phosphono)methyl]oxolan-2-yl]amino}benzoic acid 4220-99-9 [H]C(O)([C@@]1([H])OC([H])(NC2=CC=CC=C2C(O)=O)[C@]([H])(O)[C@]1([H])O)P(O)(O)=O InChI=1S/C12H16NO9P/c14-7-8(15)10(22-9(7)12(18)23(19,20)21)13-6-4-2-1-3-5(6)11(16)17/h1-4,7-10,12-15,18H,(H,16,17)(H2,19,20,21)/t7-,8+,9-,10?,12?/m0/s1 XUNHMFBIFPPJDL-NAORZKMKSA-N Cytosol logp -0.92 ALOGPS logs -1.68 ALOGPS solubility 7.28e+00 g/l ALOGPS logp -1.2 ChemAxon pka_strongest_acidic 1.25 ChemAxon pka_strongest_basic -2 ChemAxon iupac 2-{[(3R,4S,5S)-3,4-dihydroxy-5-[hydroxy(phosphono)methyl]oxolan-2-yl]amino}benzoic acid ChemAxon average_mass 349.2305 ChemAxon mono_mass 349.056267627 ChemAxon smiles [H]C(O)([C@@]1([H])OC([H])(NC2=CC=CC=C2C(O)=O)[C@]([H])(O)[C@]1([H])O)P(O)(O)=O ChemAxon formula C12H16NO9P ChemAxon inchi InChI=1S/C12H16NO9P/c14-7-8(15)10(22-9(7)12(18)23(19,20)21)13-6-4-2-1-3-5(6)11(16)17/h1-4,7-10,12-15,18H,(H,16,17)(H2,19,20,21)/t7-,8+,9-,10?,12?/m0/s1 ChemAxon inchikey XUNHMFBIFPPJDL-NAORZKMKSA-N ChemAxon polar_surface_area 176.78 ChemAxon refractivity 75.62 ChemAxon polarizability 30.25 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 10 ChemAxon donor_count 7 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Phenylalanine, tyrosine and tryptophan biosynthesis ec00400 tryptophan biosynthesis TRPSYN-PWY Specdb::CMs 1083702 Specdb::EiMs 5065 Specdb::NmrOneD 291415 Specdb::NmrOneD 291416 Specdb::NmrOneD 291417 Specdb::NmrOneD 291418 Specdb::NmrOneD 291419 Specdb::NmrOneD 291420 Specdb::NmrOneD 291421 Specdb::NmrOneD 291422 Specdb::NmrOneD 291423 Specdb::NmrOneD 291424 Specdb::NmrOneD 291425 Specdb::NmrOneD 291426 Specdb::NmrOneD 291427 Specdb::NmrOneD 291428 Specdb::NmrOneD 291429 Specdb::NmrOneD 291430 Specdb::NmrOneD 291431 Specdb::NmrOneD 291432 Specdb::NmrOneD 291433 Specdb::NmrOneD 291434 Specdb::MsMs 24479 Specdb::MsMs 24480 Specdb::MsMs 24481 Specdb::MsMs 31037 Specdb::MsMs 31038 Specdb::MsMs 31039 440289 389264 C04302 18277 N-5-PHOSPHORIBOSYL-ANTHRANILATE 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 Priestle, J. P., Grutter, M. G., White, J. L., Vincent, M. G., Kania, M., Wilson, E., Jardetzky, T. S., Kirschner, K., Jansonius, J. N. (1987). "Three-dimensional structure of the bifunctional enzyme N-(5'-phosphoribosyl)anthranilate isomerase-indole-3-glycerol-phosphate synthase from Escherichia coli." Proc Natl Acad Sci U S A 84:5690-5694. 3303031 Sterner, R., Kleemann, G. R., Szadkowski, H., Lustig, A., Hennig, M., Kirschner, K. (1996). "Phosphoribosyl anthranilate isomerase from Thermotoga maritima is an extremely stable and active homodimer." Protein Sci 5:2000-2008. 8897600 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 N-(5-Phospho-D-ribosyl)anthranilate > 1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate R03509 PRAISOM-RXN 2-Aminobenzoic acid + Phosphoribosyl pyrophosphate > Pyrophosphate + N-(5-Phospho-D-ribosyl)anthranilate R01073 PRTRANS-RXN N-(5-Phospho-D-ribosyl)anthranilate + Pyrophosphate <> 2-Aminobenzoic acid + Phosphoribosyl pyrophosphate R01073 N-(5-Phospho-D-ribosyl)anthranilate <> 1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate R03509 N-(5-Phospho-D-ribosyl)anthranilate + Pyrophosphate < 2-Aminobenzoic acid + Phosphoribosyl pyrophosphate PRTRANS-RXN N-(5-Phospho-D-ribosyl)anthranilate + Pyrophosphate > 2-Aminobenzoic acid + Phosphoribosyl pyrophosphate