Identification
YMDB IDYMDB00054
NameN-(5-phospho-beta-D-ribosyl)anthranilic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionN-(5-phospho-beta-D-ribosyl)anthranilic acid, also known as NPRAT, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. N-(5-phospho-beta-D-ribosyl)anthranilic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). N-(5-phospho-beta-D-ribosyl)anthranilic acid exists in both E. coli (prokaryote) and yeast (eukaryote).
Structure
Thumb
Synonyms
  • N-(2-carboxylatophenyl)-5-O-phosphonato-beta-D-ribofuranosylamine
  • N-(5-Phospho-beta-D-ribosyl)anthranilate
  • N-(5-Phospho-D-ribosyl)anthranilate
  • N-(5-Phosphoribosyl)anthranilate
  • N-(5-Phosphoribosyl)anthranilic acid
  • N-(5'-Phosphoribosyl)anthranilate
  • N-(5'-Phosphoribosyl)anthranilic acid
  • NPRAT
  • N-(5-Phospho-b-D-ribosyl)anthranilate
  • N-(5-Phospho-b-D-ribosyl)anthranilic acid
  • N-(5-Phospho-β-D-ribosyl)anthranilate
  • N-(5-Phospho-β-D-ribosyl)anthranilic acid
  • N-(5-phospho-D-Ribosyl)anthranilic acid
  • N-(5-Phospho-beta-D-ribosyl)anthranilic acid
CAS numberNot Available
WeightAverage: 349.2305
Monoisotopic: 349.056267627
InChI KeyPMFMJXPRNJUYMB-GWOFURMSSA-N
InChIInChI=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)/t8-,9-,10-,11-/m1/s1
IUPAC Name2-{[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]amino}benzoic acid
Traditional IUPAC Namenprat
Chemical FormulaC12H16NO9P
SMILESO[C@H]1[C@@H](O)[C@H](NC2=CC=CC=C2C(O)=O)O[C@@H]1COP(O)(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose-5-phosphate
  • Pentose phosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Benzoic acid
  • Benzoic acid or derivatives
  • Phenylalkylamine
  • Aniline or substituted anilines
  • Benzoyl
  • Monoalkyl phosphate
  • Secondary aliphatic/aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Benzenoid
  • Alkyl phosphate
  • Monocyclic benzene moiety
  • Vinylogous amide
  • Tetrahydrofuran
  • Secondary alcohol
  • Amino acid or derivatives
  • 1,2-diol
  • Amino acid
  • Secondary amine
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Amine
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.5 g/LALOGPS
logP-1ALOGPS
logP-0.15ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area165.78 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity76.08 m³·mol⁻¹ChemAxon
Polarizability30.59 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Phenylalanine, tyrosine and tryptophan biosynthesisec00400 Map00400
SMPDB ReactionsNot Available
KEGG Reactions
2-Aminobenzoic acid + Phosphoribosyl pyrophosphatePyrophosphate + N-(5-phospho-beta-D-ribosyl)anthranilic acid
N-(5-phospho-beta-D-ribosyl)anthranilic acid1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_10) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1539000000-afa303df223fc236b2a8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uej-6796000000-d8aec7db3c63af996744JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2910000000-a2f91d8bb4e2ccda7cd1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-005a-3904000000-63d42279e1736d1159fdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9201000000-2cfcddd5b31d906f0cb2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-b5c17b0df8b3db541b9eJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Hommel, U., Lustig, A., Kirschner, K. (1989). "Purification and characterization of yeast anthranilate phosphoribosyltransferase." Eur J Biochem 180:33-40.2651124
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Miozzari, G., Niederberger, P., Hutter, R. (1978). "Tryptophan biosynthesis in Saccharomyces cerevisiae: control of the flux through the pathway." J Bacteriol 134:48-59.348687
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID7091
HMDB IDNot Available
Pubchem Compound ID440289
Kegg IDC04302
ChemSpider ID389264
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in anthranilate phosphoribosyltransferase activity
Specific function:
N-(5-phospho-D-ribosyl)-anthranilate + diphosphate = anthranilate + 5-phospho-alpha-D-ribose 1- diphosphate
Gene Name:
TRP4
Uniprot ID:
P07285
Molecular weight:
41374.0
Reactions
N-(5-phospho-D-ribosyl)-anthranilate + diphosphate → anthranilate + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in catalytic activity
Specific function:
N-(5-phospho-beta-D-ribosyl)anthranilate = 1- (2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate
Gene Name:
TRP1
Uniprot ID:
P00912
Molecular weight:
24144.30078
Reactions
N-(5-phospho-beta-D-ribosyl)anthranilate → 1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate.