MetaCyc Compound: 2-keto-D-gluconate

Synonyms: 2-dehydro-D-gluconate

Chemical Formula: C6H9O7

Molecular Weight: 193.13 Daltons

Monoisotopic Molecular Weight: 194.0426526757 Daltons

2-keto-D-gluconate compound structure

SMILES: C(C(C(C(C(CO)O)O)O)=O)([O-])=O

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)/p-1/t2-,3-,4+/m1/s1


Unification Links: ChEBI:16808 , ChemSpider:5256721 , IAF1260:1482981 , KEGG:C06473 , PubChem:6857381

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -166.05197 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

glucose degradation (oxidative) :
2-keto-D-gluconate + ATP → 6-phospho-2-dehydro-D-gluconate + ADP + H+

ketogluconate metabolism :
D-gluconate + NADP+2-keto-D-gluconate + NADPH + H+

L-ascorbate biosynthesis VI (engineered pathway) :
2-keto-D-gluconate + an oxidized unknown electron acceptor → 2,5-didehydro-D-gluconate + an reduced unknown electron acceptor

Reactions known to produce the compound:

glucose degradation (oxidative) , L-ascorbate biosynthesis VI (engineered pathway) :
D-gluconate + an oxidized unknown electron acceptor → 2-keto-D-gluconate + an reduced unknown electron acceptor

Reactions known to both consume and produce the compound:

ketogluconate metabolism , L-ascorbate biosynthesis VI (engineered pathway) :
2-keto-D-gluconate + NADP+ ↔ 2,5-didehydro-D-gluconate + NADPH + H+

In Reactions of unknown directionality:

Not in pathways:
D-gluconate + FAD + H+ = 2-keto-D-gluconate + FADH2

Enzymes inhibited by 2-keto-D-gluconate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: α-dehydro-β-deoxy-D-glucarate aldolase [Fish66]

This compound has been characterized as an alternative substrate of the following enzymes: 2-keto-6-phosphogluconate reductase


Fish66: Fish D, Blumenthal H "2-keto-3-deoxy-D-glucarate aldolase." Meth Enz 1966;9:529-534.

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Mon Oct 5, 2015, biocyc13.