Record Information
Version2.0
Creation Date2012-05-31 14:31:26 -0600
Update Date2015-06-03 17:19:27 -0600
Secondary Accession Numbers
  • ECMDB20174
Identification
Name:N-(5-Phospho-D-ribosyl)anthranilate
DescriptionN-(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)
Structure
Thumb
Synonyms:
  • 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
Chemical Formula:C12H16NO9P
Weight:Average: 349.2305
Monoisotopic: 349.056267627
InChI Key:XUNHMFBIFPPJDL-NAORZKMKSA-N
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
CAS number:4220-99-9
IUPAC Name:2-{[(3R,4S,5S)-3,4-dihydroxy-5-[hydroxy(phosphono)methyl]oxolan-2-yl]amino}benzoic acid
Traditional IUPAC Name:2-{[(3R,4S,5S)-3,4-dihydroxy-5-[hydroxy(phosphono)methyl]oxolan-2-yl]amino}benzoic acid
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
Chemical Taxonomy
ClassificationNot classified
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility7.28 g/LALOGPS
logP-0.92ALOGPS
logP-1.2ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)1.25ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area176.78 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity75.62 m³·mol⁻¹ChemAxon
Polarizability30.25 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
  • Phenylalanine, tyrosine and tryptophan biosynthesis ec00400
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uyi-0819000000-95763a6f1989f32a6dfcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9433000000-4e0c9f04cee4b88d0d04View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fe0-2900000000-e8ee92a0ccd03173d26eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-2914000000-4ff300d6805ac0d243b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f8i-9875000000-1c37f28497b620c1a45bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-005l-8900000000-9b8b58fda98d39398bd4View in MoNA
References
References:
  • 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. Pubmed: 22080510
  • 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. Pubmed: 21097882
  • 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. Pubmed: 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. Pubmed: 8897600
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18277
HMDB IDNot Available
Pubchem Compound ID440289
Kegg IDC04302
ChemSpider ID389264
Wikipedia IDNot Available
BioCyc IDN-5-PHOSPHORIBOSYL-ANTHRANILATE
EcoCyc IDN-5-PHOSPHORIBOSYL-ANTHRANILATE

Enzymes

General function:
Involved in anthranilate phosphoribosyltransferase activity
Specific function:
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate
Gene Name:
trpD
Uniprot ID:
P00904
Molecular weight:
56869
Reactions
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate.
N-(5-phospho-D-ribosyl)-anthranilate + diphosphate = anthranilate + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in catalytic activity
Specific function:
Bifunctional enzyme that catalyzes two sequential steps of tryptophan biosynthetic pathway. The first reaction is catalyzed by the isomerase, coded by the trpF domain; the second reaction is catalyzed by the synthase, coded by the trpC domain
Gene Name:
trpC
Uniprot ID:
P00909
Molecular weight:
49361
Reactions
N-(5-phospho-beta-D-ribosyl)anthranilate = 1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate.
1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate = 1-C-(3-indolyl)-glycerol 3-phosphate + CO(2) + H(2)O.