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2-Dehydro-D-gluconate (M2MDB000575)

Record Information
Version2.0
Creation Date2012-05-31 14:03:06 -0600
Update Date2015-09-17 15:41:46 -0600
Secondary Accession Numbers
  • ECMDB04042
Identification
Name:2-Dehydro-D-gluconate
Description2-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. E. coli contains ketogluconate reductase genes, so it is likely that pathways exist for the metabolism of ketogluconate
Structure
Thumb
MOLSDFPDBSMILESInChI
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
Weight:Average: 194.1394
Monoisotopic: 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
Description belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar acids and derivatives
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Medium-chain keto acid
  • Beta-hydroxy acid
  • Sugar acid
  • Acyloin
  • Alpha-keto acid
  • Beta-hydroxy ketone
  • Hydroxy acid
  • Keto acid
  • Monosaccharide
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic 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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.65 m³·mol⁻¹ChemAxon
Polarizability16.29 ųChemAxon
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
2-Dehydro-D-gluconate + NADP > 2,5-didehydro-D-gluconate + NADPH
Gluconic acid + NADP > 2-Dehydro-D-gluconate + NADPH
2-Dehydro-D-gluconate + NADP <> 2,5-Diketo-D-gluconate + NADPH + Hydrogen ion
2-Keto-L-gluconate + Hydrogen ion + NADPH + 2-Dehydro-D-gluconate + NADPH > NADP + L-Idonate
2,5-Diketo-D-gluconate + Hydrogen ion + NADPH + NADPH > NADP + 2-Keto-L-gluconate + 2-Dehydro-D-gluconate
2-Keto-L-gluconate + NADPH + Hydrogen ion + 2-Dehydro-D-gluconate + NADPH > Gluconic acid + NADP
2 2-Dehydro-D-gluconate + NADP <>2 2,5-Diketo-D-gluconate + NADPH + Hydrogen ion
SMPDB Pathways:
ketogluconate metabolismPW002003 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
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

Enzymes

Protein Details
1. 2,5-diketo-D-gluconic acid reductase B
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the reduction of 2,5-diketo-D-gluconic acid (25DKG) to 2-keto-L-gulonic acid (2KLG)
Gene Name:
dkgB
Uniprot ID:
P30863
Molecular weight:
29437
Reactions
2-dehydro-D-gluconate + NADP(+) = 2,5-didehydro-D-gluconate + NADPH.
Protein Details
2. Glyoxylate/hydroxypyruvate reductase B
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Catalyzes the NADPH-dependent reduction of glyoxylate and hydroxypyruvate into glycolate and glycerate, respectively. Can also reduce 2,5-diketo-D-gluconate (25DKG) to 5-keto-D- gluconate (5KDG), 2-keto-D-gluconate (2KDG) to D-gluconate, and 2- keto-L-gulonate (2KLG) to L-idonate (IA), but it is not its physiological function. Inactive towards 2-oxoglutarate, oxaloacetate, pyruvate, 5-keto-D-gluconate, D-fructose and L- sorbose. Activity with NAD is very low
Gene Name:
ghrB
Uniprot ID:
P37666
Molecular weight:
35395
Reactions
Glycolate + NADP(+) = glyoxylate + NADPH.
D-glycerate + NAD(P)(+) = hydroxypyruvate + NAD(P)H.
D-gluconate + NADP(+) = 2-dehydro-D-gluconate + NADPH.
Protein Details
3. 2,3-diketo-L-gulonate reductase
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Catalyzes the reduction of 2,3-diketo-L-gulonate in the presence of NADH, to form 3-keto-L-gulonate
Gene Name:
dlgD
Uniprot ID:
P37672
Molecular weight:
36572
Reactions
3-dehydro-L-gulonate + NAD(P)(+) = (4R,5S)-4,5,6-trihydroxy-2,3-dioxohexanoate + NAD(P)H.
Protein Details
4. 2,5-diketo-D-gluconic acid reductase A
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the reduction of 2,5-diketo-D-gluconic acid (25DKG) to 2-keto-L-gulonic acid (2KLG). It is also capable of stereoselective -keto ester reductions on ethyl acetoacetate and other 2-substituted derivatives
Gene Name:
dkgA
Uniprot ID:
Q46857
Molecular weight:
31109
Reactions
2-dehydro-D-gluconate + NADP(+) = 2,5-didehydro-D-gluconate + NADPH.