2-Dehydro-D-gluconate (PAMDB000575)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000575
Identification
Name: 2-Dehydro-D-gluconate
Description:2-Keto-L-gluconate is a derivative of gluconic acid, which occurs naturally in fruit, honey and wine and is used as a food additive, an acidity regulator. It is also used in cleaning products where it helps cleaning up mineral deposits. It is a strong chelating agent, especially in alkaline solution. It chelates the anions of calcium, iron, aluminium, copper, and other heavy metals. Pseudomonas aeruginosa contains ketogluconate reductase genes, so it is likely that pathways exist for the metabolism of ketogluconate
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2-Dehydro-D-gluconate
  • 2-Dehydro-D-gluconic acid
  • 2-Dehydro-L-idonate
  • 2-Dehydro-L-idonic acid
  • 2-Keto-D-gluconate
  • 2-Keto-D-gluconic acid
  • 2-Keto-L-gulonate
  • 2-Keto-L-gulonic acid
  • 2-Ketoidonate
  • 2-Ketoidonic acid
  • 2-Oxogluconate
  • 2-Oxogluconic acid
  • L-Ketoidonate
  • L-Ketoidonic acid
  • L-Sorbosonate
  • L-Sorbosonic acid
  • Provitamin C
Chemical Formula: C6H10O7
Average Molecular Weight: 194.1394
Monoisotopic Molecular Weight: 194.042652674
InChI Key: VBUYCZFBVCCYFD-UHFFFAOYSA-N
InChI:InChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-4,7-10H,1H2,(H,12,13)
CAS number: Not Available
IUPAC Name:(3S,4R,5R)-3,4,5,6-tetrahydroxy-2-oxohexanoic acid
Traditional IUPAC Name: 2-ketogluconic acid
SMILES:OCC(O)C(O)C(O)C(=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as sugar acids and derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassSugar acids and derivatives
Direct Parent Sugar acids and derivatives
Alternative Parents
Substituents
  • Hydroxy fatty acid
  • Medium-chain keto acid
  • Sugar acid
  • Beta-hydroxy acid
  • Fatty acyl
  • Monosaccharide
  • Keto acid
  • Hydroxy acid
  • Beta-hydroxy ketone
  • Beta-ketoaldehyde
  • Alpha-keto acid
  • Acyloin
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Polyol
  • Ketone
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: 157.82
Experimental Properties:
PropertyValueSource
Water Solubility:1PhysProp
Predicted Properties
PropertyValueSource
Water Solubility101.0 mg/mLALOGPS
logP-2.4ALOGPS
logP-2.5ChemAxon
logS-0.28ALOGPS
pKa (Strongest Acidic)2.67ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area135.29 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.65 m3·mol-1ChemAxon
Polarizability16.29 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Gluconic acid + NADP <> 2-Keto-D-gluconic acid + NADPH + Hydrogen ion + 2-Dehydro-D-gluconate
NADP + Gluconic acid <> Hydrogen ion + 2-Dehydro-D-gluconate + NADPH
Hydrogen ion + NADPH + 2,5-Diketo-D-gluconate <> 2-Dehydro-D-gluconate + NADP
Hydrogen ion + 2-Dehydro-D-gluconate + NADPH <> L-Idonate + NADP
Gluconic acid + NADP > 2-Dehydro-D-gluconate + NADPH
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 5 TMS)splash10-0udi-1932000000-1a7cf25a47cef7e76764View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 5 TMS)splash10-0uxr-1941000000-5e906d17255b5032ec96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-1900000000-4c70f69302f31c33ee5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-9600000000-f027c92665e4c348f2a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-9100000000-97f3ffedc2a208b66d5eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0feu-8900000000-bc1bb85704615258ff49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pbi-9400000000-004d1425c619a87cd240View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-9100000000-d0a0104e3be31e2d9161View 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
  • 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
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID27469
HMDB IDHMDB11732
Pubchem Compound ID50
Kegg IDC06473
ChemSpider ID49
Wikipedia IDNot Available
BioCyc IDCPD-377
EcoCyc IDCPD-377