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Record Information
Version	2.0
Creation Date	2012-05-31 13:51:17 -0600
Update Date	2015-06-03 15:54:04 -0600
Secondary Accession Numbers	ECMDB01376
Identification
Name:	2-Keto-3-deoxy-6-phosphogluconic acid
Description	2-Keto-3-deoxy-6-phosphogluconic acid is a substrate for Fructose-bisphosphate aldolase A.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa02b7b68> Close
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.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Keto acids and derivatives
Sub Class	Medium-chain keto acids and derivatives
Direct Parent	Medium-chain keto acids and derivatives
Alternative Parents	Monoalkyl phosphates Beta-hydroxy ketones Alpha-keto acids and derivatives Alpha-hydroxy ketones Secondary alcohols 1,2-diols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives
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 Framework	Aliphatic acyclic compounds
External Descriptors	ketoaldonic acid phosphate (CHEBI:15925 )
Physical Properties
State:	Solid
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 14.3 g/L ALOGPS logP -2.4 ALOGPS logP -1.9 ChemAxon logS -1.3 ALOGPS pKa (Strongest Acidic) 1.48 ChemAxon pKa (Strongest Basic) -3.3 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 8 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 161.59 Ų ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 47.19 m³·mol⁻¹ ChemAxon Polarizability 20.17 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	2-Keto-3-deoxy-6-phosphogluconic acid <> D-Glyceraldehyde 3-phosphate + Pyruvic acid 6-Phosphogluconic acid <> 2-Keto-3-deoxy-6-phosphogluconic acid + Water 2-Keto-3-deoxy-D-gluconic acid + Adenosine triphosphate <> 2-Keto-3-deoxy-6-phosphogluconic acid + ADP + Hydrogen ion Adenosine triphosphate + 2-Keto-3-deoxy-D-gluconic acid <> ADP + 2-Keto-3-deoxy-6-phosphogluconic acid 2-Keto-3-deoxy-D-gluconic acid + Adenosine triphosphate > Hydrogen ion + 2-Keto-3-deoxy-6-phosphogluconic acid + ADP 2-Keto-3-deoxy-6-phosphogluconic acid > D-Glyceraldehyde 3-phosphate + Pyruvic acid 6-Phosphogluconic acid > 2-Keto-3-deoxy-6-phosphogluconic acid + Water Adenosine triphosphate + 2-Keto-3-deoxy-D-gluconic acid > ADP + 2-Keto-3-deoxy-6-phosphogluconic acid 2-Dehydro-3-deoxy-D-galactonate + Adenosine triphosphate + 2-Keto-3-deoxy-D-gluconic acid > Hydrogen ion + 2-Keto-3-deoxy-6-phosphogluconic acid + Adenosine diphosphate + ADP 2-Keto-3-deoxy-6-phosphogluconic acid > D-Glyceraldehyde 3-phosphate + Pyruvic acid + D-Glyceraldehyde 3-phosphate gluconate 6-phosphate > Water + 2-Keto-3-deoxy-6-phosphogluconic acid 6 6-Phosphogluconic acid <>2 2-Keto-3-deoxy-6-phosphogluconic acid + Water
SMPDB Pathways:	hexuronide and hexuronate degradation PW000834 ketogluconate metabolism PW002003
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:	β-D-glucuronide and D-glucuronate degradation GLUCUROCAT-PWY D-galacturonate degradation I GALACTUROCAT-PWY Entner-Doudoroff pathway I ENTNER-DOUDOROFF-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0002-9310000000-b977edea41f10c14441f View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive splash10-01bc-6921400000-ca4d77ba878e92aaedf5 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-052f-1490000000-ea0f4bddcb2b9a63fa4f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-01vy-6940000000-6658b367949c0aff033c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0076-9700000000-5dfc9ad3d3a20de41780 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0a70-8290000000-46b63c8be3e78b565ecd View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9100000000-969c103f10917fe5078a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-6b6797b8569981c766a4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-06r7-6590000000-4bfcef169935d1cae20e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0002-9200000000-17589b3b796f6001e623 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0005-9000000000-cd26445e4e826ec3239a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0002-9040000000-51b487070c5625d5eab9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004j-9000000000-5c6f9eb036b780095d5a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-d484c197bb695cc95948 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View 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
Links
External Links:	Resource Link CHEBI ID 15925 HMDB ID HMDB01376 Pubchem Compound ID 3080745 Kegg ID C04442 ChemSpider ID 2338483 Wikipedia ID Not Available BioCyc ID 2-KETO-3-DEOXY-6-P-GLUCONATE EcoCyc ID 2-KETO-3-DEOXY-6-P-GLUCONATE

Enzymes