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1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate (M2MDB000868)

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
MOLSDFPDBSMILESInChI
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:
1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate + Hydrogen ion <> Indoleglycerol phosphate + Carbon dioxide + Water
N-(5-Phospho-D-ribosyl)anthranilate > 1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate
1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate <> Indoleglycerol phosphate + Carbon dioxide + Water
N-(5-Phospho-D-ribosyl)anthranilate <> 1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate
Hydrogen ion + 1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate > Indoleglycerol phosphate + Carbon dioxide + Water
N-(5-phospho-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 + Carbon dioxide + Water
1-(2-Carboxyphenylamino)-1'-deoxy-D-ribulose 5'-phosphate + Hydrogen ion <> Indoleglycerol phosphate + Carbon dioxide + Water
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
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
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

Protein Details
1. Tryptophan biosynthesis protein trpCF
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.