Record Information
Version2.0
Creation Date2012-05-31 13:51:17 -0600
Update Date2015-06-03 15:54:04 -0600
Secondary Accession Numbers
  • ECMDB01376
Identification
Name:2-Keto-3-deoxy-6-phosphogluconic acid
Description2-Keto-3-deoxy-6-phosphogluconic acid is a substrate for Fructose-bisphosphate aldolase A.
Structure
Thumb
Synonyms:
  • 2-Dehydro-3-deoxy-6-phospho-D-gluconate
  • 2-Dehydro-3-deoxy-6-phospho-D-gluconic acid
  • 2-dehydro-3-Deoxy-D-gluconate 6-phosphate
  • 2-Dehydro-3-deoxy-D-gluconate-6-phosphate
  • 2-dehydro-3-Deoxy-D-gluconic acid-6-phosphoric acid
  • 2-Keto-3-deoxy-6-P-gluconate
  • 2-Keto-3-deoxy-6-P-gluconic acid
  • 2-Keto-3-deoxy-6-phospho-D-gluconate
  • 2-Keto-3-deoxy-6-phospho-D-gluconic acid
  • 2-Keto-3-deoxy-6-phospho-Gluconate
  • 2-Keto-3-deoxy-6-phospho-Gluconic acid
  • 2-Keto-3-deoxy-6-phosphogluconate
  • 2-Keto-3-deoxy-6-phosphogluconic acid
  • 2-Keto-3-deoxygluconate-6-P
  • 2-keto-3-Deoxygluconic acid-6-P
  • 3-deoxy-D-erythro-hex-2-ulosonate-6-phosphate
  • 3-deoxy-D-erythro-hex-2-ulosonic acid 6-phosphate
  • 3-Deoxy-D-erythro-hex-2-ulosonate 6-phosphate
  • 3-Deoxy-D-erythro-hex-2-ulosonate-6-phosphate
  • 3-Deoxy-D-erythro-hex-2-ulosonic acid 6-phosphate
  • 3-Deoxy-D-erythro-hex-2-ulosonic acid 6-phosphoric acid
  • 3-Deoxy-D-erythro-hex-2-ulosonic acid-6-phosphoric acid
  • 6-p-2-k-3-Deo-gluconate
  • 6-p-2-k-3-Deo-gluconic acid
  • 6-Phospho-2-dehydro-3-deoxy-D-gluconate
  • 6-Phospho-2-dehydro-3-deoxy-D-gluconic acid
  • 6-Phospho-2-dehydro-3-deoxygluconate
  • 6-Phospho-2-dehydro-3-deoxygluconic acid
  • 6-Phospho-2-keto-3-deoxygluconate
  • 6-Phospho-2-keto-3-deoxygluconic acid
  • KDPGlcA
Chemical Formula:C6H11O9P
Weight:Average: 258.1199
Monoisotopic: 258.014068462
InChI Key:OVPRPPOVAXRCED-WVZVXSGGSA-N
InChI:InChI=1S/C6H11O9P/c7-3(1-4(8)6(10)11)5(9)2-15-16(12,13)14/h3,5,7,9H,1-2H2,(H,10,11)(H2,12,13,14)/t3-,5+/m0/s1
CAS number:27244-54-8
IUPAC Name:(4S,5R)-4,5-dihydroxy-2-oxo-6-(phosphonooxy)hexanoic acid
Traditional IUPAC Name:kdpg intermediate
SMILES:O[C@H](COP(O)(O)=O)[C@@H](O)CC(=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassMedium-chain keto acids and derivatives
Direct ParentMedium-chain keto acids and derivatives
Alternative Parents
Substituents
  • Medium-chain keto acid
  • Monoalkyl phosphate
  • Alpha-keto acid
  • Beta-hydroxy ketone
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Alpha-hydroxy ketone
  • Ketone
  • 1,2-diol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility14.3 g/LALOGPS
logP-2.4ALOGPS
logP-1.9ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)1.48ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area161.59 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity47.19 m³·mol⁻¹ChemAxon
Polarizability20.17 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
hexuronide and hexuronate degradationPW000834 ThumbThumb?image type=greyscaleThumb?image type=simple
ketogluconate metabolismPW002003 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Arginine and proline metabolism ec00330
  • Glyoxylate and dicarboxylate metabolism ec00630
  • Metabolic pathways eco01100
  • Microbial metabolism in diverse environments ec01120
  • Pentose and glucuronate interconversions ec00040
  • Pentose phosphate pathway ec00030
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9310000000-b977edea41f10c14441fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01bc-6921400000-ca4d77ba878e92aaedf5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-1490000000-ea0f4bddcb2b9a63fa4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01vy-6940000000-6658b367949c0aff033cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0076-9700000000-5dfc9ad3d3a20de41780View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a70-8290000000-46b63c8be3e78b565ecdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-969c103f10917fe5078aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-6b6797b8569981c766a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06r7-6590000000-4bfcef169935d1cae20eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9200000000-17589b3b796f6001e623View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9000000000-cd26445e4e826ec3239aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9040000000-51b487070c5625d5eab9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9000000000-5c6f9eb036b780095d5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-d484c197bb695cc95948View in MoNA
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
1D NMR13C 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • 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 ID15925
HMDB IDHMDB01376
Pubchem Compound ID3080745
Kegg IDC04442
ChemSpider ID2338483
Wikipedia IDNot Available
BioCyc ID2-KETO-3-DEOXY-6-P-GLUCONATE
EcoCyc ID2-KETO-3-DEOXY-6-P-GLUCONATE

Enzymes

General function:
Involved in catalytic activity
Specific function:
4-hydroxy-2-oxoglutarate = pyruvate + glyoxylate
Gene Name:
eda
Uniprot ID:
P0A955
Molecular weight:
22284
Reactions
4-hydroxy-2-oxoglutarate = pyruvate + glyoxylate.
2-dehydro-3-deoxy-D-gluconate 6-phosphate = pyruvate + D-glyceraldehyde 3-phosphate.
General function:
Involved in phosphogluconate dehydratase activity
Specific function:
6-phospho-D-gluconate = 2-dehydro-3-deoxy-6- phospho-D-gluconate + H(2)O
Gene Name:
edd
Uniprot ID:
P0ADF6
Molecular weight:
64639
Reactions
6-phospho-D-gluconate = 2-dehydro-3-deoxy-6-phospho-D-gluconate + H(2)O.
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
ATP + 2-dehydro-3-deoxy-D-gluconate = ADP + 6- phospho-2-dehydro-3-deoxy-D-gluconate
Gene Name:
kdgK
Uniprot ID:
P37647
Molecular weight:
33962
Reactions
ATP + 2-dehydro-3-deoxy-D-gluconate = ADP + 6-phospho-2-dehydro-3-deoxy-D-gluconate.