Record Information
Version2.0
Creation Date2012-05-31 14:23:12 -0600
Update Date2015-06-03 17:19:08 -0600
Secondary Accession Numbers
  • ECMDB20019
Identification
Name:1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate
Description1-(2-carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate is a pentose phosphate derivative. It is a substrate for indole-3-glycerol-phosphate synthase (IPGS) (EC 4.1.1.48)which is an enzyme that catalyzes the chemical reaction: 1-(2-carboxyphenylamino)-1-deoxy-D-ribulose 5-phosphate ightleftharpoons 1-C-(indol-3-yl)-glycerol 3-phosphate + CO2 + H2O
Structure
Thumb
Synonyms:
  • 1-(2-carboxyphenylamino)-1'-Deoxy-D-ribulose 5'-phosphoric acid
  • 1-(2-Carboxyphenylamino)-1-deoxy-D-ribulose-5-P
  • 1-(2-Carboxyphenylamino)-1-deoxy-D-ribulose-5-phosphate
  • 1-(2-carboxyphenylamino)-1-Deoxy-D-ribulose-5-phosphoric acid
  • 1-(O-Carboxyphenylamino)-1'-deoxyribulose-5'-P
  • 1-(O-Carboxyphenylamino)-1'-deoxyribulose-5'-phosphate
  • 1-(O-carboxyphenylamino)-1'-Deoxyribulose-5'-phosphoric acid
  • Carboxyphenylamino-deoxyribulose-p
  • CPADRP
Chemical Formula:C12H16NO9P
Weight:Average: 349.2305
Monoisotopic: 349.056267627
InChI Key:QKMBYNRMPRKVTO-MNOVXSKESA-N
InChI:InChI=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
CAS number:Not Available
IUPAC Name:2-{[(3R,4R)-3,4-dihydroxy-2-oxo-5-(phosphonooxy)pentyl]amino}benzoic acid
Traditional IUPAC Name:2-{[(3R,4R)-3,4-dihydroxy-2-oxo-5-(phosphonooxy)pentyl]amino}benzoic acid
SMILES:O[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
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
  • Metabolic pathways eco01100
  • Phenylalanine, tyrosine and tryptophan biosynthesis ec00400
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-5911000000-37b09c66588c632153beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0339000000-69722cac0a11d3f77f39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udm-1921000000-c609a3aa34bcb82cfcfdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-3900000000-a5ab2361731c8e108c8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6s-4955000000-a019a420bd68acd6c195View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9410000000-f6a1776a0ae271fef65dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-6a98c0c5e5f9775e0b22View 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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID29112
HMDB IDNot Available
Pubchem Compound ID287
Kegg IDC01302
ChemSpider ID394132
Wikipedia IDNot Available
BioCyc IDCARBOXYPHENYLAMINO-DEOXYRIBULOSE-P
EcoCyc IDCARBOXYPHENYLAMINO-DEOXYRIBULOSE-P

Enzymes

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.