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Identification
YMDB IDYMDB00251
Name1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate, also known as 1-[(2-carboxyphenyl)amino]-1-deoxy-5-O-phosphono-D-ribulose, 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. 1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). 1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate exists in both E. coli (prokaryote) and yeast (eukaryote). 1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate can be biosynthesized from N-(5-phosphoribosyl)-anthranilate through its interaction with the enzyme N-(5'-phosphoribosyl)anthranilate isomerase. In yeast, 1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate is involved in the metabolic pathway called the tryptophan metabolism pathway.
Structure
Thumb
Synonyms
  • 1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate
  • 1-[(2-carboxyphenyl)amino]-1-deoxy-5-O-phosphono-D-ribulose
  • 1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphoric acid
  • 1-(2-Carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphoric acid
  • 1-(2-Carboxyphenylamino)-1-deoxyribulose 5-phosphate
CAS number5962-18-5
WeightAverage: 349.2305
Monoisotopic: 349.056267627
InChI KeyQKMBYNRMPRKVTO-MNOVXSKESA-N
InChIInChI=1S/C12H16NO9P/c14-9(11(16)10(15)6-22-23(19,20)21)5-13-8-4-2-1-3-7(8)12(17)18/h1-4,10-11,13,15-16H,5-6H2,(H,17,18)(H2,19,20,21)/t10-,11+/m1/s1
IUPAC Name2-{[(3R,4R)-3,4-dihydroxy-2-oxo-5-(phosphonooxy)pentyl]amino}benzoic acid
Traditional IUPAC Name2-{[(3R,4R)-3,4-dihydroxy-2-oxo-5-(phosphonooxy)pentyl]amino}benzoic acid
Chemical FormulaC12H16NO9P
SMILESO[C@H](COP(O)(O)=O)[C@@H](O)C(=O)CNC1=C(C=CC=C1)C(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
  • Aminobenzoic acid or derivatives
  • Aminobenzoic acid
  • Monosaccharide phosphate
  • Benzoic acid
  • Benzoic acid or derivatives
  • Benzoyl
  • Phenylalkylamine
  • Aniline or substituted anilines
  • Monoalkyl phosphate
  • Secondary aliphatic/aromatic amine
  • Alkyl phosphate
  • Beta-hydroxy ketone
  • Phosphoric acid ester
  • Monocyclic benzene moiety
  • Organic phosphoric acid derivative
  • Benzenoid
  • Acyloin
  • Alpha-hydroxy ketone
  • Alpha-aminoketone
  • 1,3-aminoalcohol
  • Vinylogous amide
  • Ketone
  • Amino acid or derivatives
  • Secondary alcohol
  • Amino acid
  • 1,2-diol
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.55 g/LALOGPS
logP-0.91ALOGPS
logP-0.5ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.48ChemAxon
pKa (Strongest Basic)0.27ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area173.62 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity77.72 m³·mol⁻¹ChemAxon
Polarizability30.76 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Tryptophan metabolismPW002442 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Phenylalanine, tyrosine and tryptophan biosynthesisec00400 Map00400
Tryptophan metabolismec00380 Map00380
SMPDB Reactions
N-(5-Phosphonato-beta-D-ribosyl)anthranilate1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate
KEGG Reactions
1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate + hydron1-C-(indol-3-yl)glycerol 3-phosphate + Carbon dioxide + water
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
  • 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
  • Zalkin, H., Paluh, J. L., van Cleemput, M., Moye, W. S., Yanofsky, C. (1984). "Nucleotide sequence of Saccharomyces cerevisiae genes TRP2 and TRP3 encoding bifunctional anthranilate synthase: indole-3-glycerol phosphate synthase." J Biol Chem 259:3985-3992.6323449
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID29112
HMDB IDNot Available
Pubchem Compound ID446894
Kegg IDC01302
ChemSpider ID24784954
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate
Gene Name:
TRP3
Uniprot ID:
P00937
Molecular weight:
53488.89844
Reactions
Chorismate + L-glutamine → anthranilate + pyruvate + L-glutamate.
1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate → 1-C-(3-indolyl)-glycerol 3-phosphate + CO(2) + H(2)O.
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.