1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate (YMDB00251)

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).
Structure
Thumb
MOLSDFPDBSMILESInChI
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)anthranilate → 1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate
KEGG Reactions
1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate + hydron → 1-C-(indol-3-yl)glycerol 3-phosphate + Carbon dioxide + water
N-(5-phospho-beta-D-ribosyl)anthranilic acid → 1-(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 (Non-derivatized) - 70eV, Positivesplash10-0005-5911000000-37b09c66588c632153beJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0339000000-69722cac0a11d3f77f39JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udm-1921000000-c609a3aa34bcb82cfcfdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-3900000000-a5ab2361731c8e108c8dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6s-4955000000-a019a420bd68acd6c195JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9410000000-f6a1776a0ae271fef65dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-6a98c0c5e5f9775e0b22JSpectraViewer
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
  • 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

Protein Details
1. Anthranilate synthase component 2
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.
Protein Details
2. N-(5'-phosphoribosyl)anthranilate isomerase
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.