Canmetcon
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Identification
YMDB IDYMDB00054
NameN-(5-phospho-beta-D-ribosyl)anthranilic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionN-(5'-Phosphoribosyl)-anthranilate is an intermediate in tryptophan biosynthesis pathway. [Biocyc TRPSYN-PWY]
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-beta-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
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
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.