MetaCyc Compound: 2,3-dioxo-L-gulonate

Synonyms: (4R,5S)-4,5,6-trihydroxy-2,3-dioxohexanoate, 2,3-diketo-L-gulonate, DKG, L-xylo-hex-2-enonic acid, L-xylo-hex-2-enonate

Chemical Formula: C6H7O7

Molecular Weight: 191.12 Daltons

Monoisotopic Molecular Weight: 192.0270026115 Daltons

2,3-dioxo-L-gulonate compound structure

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

InChI: InChI=1S/C6H8O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-3,7-9H,1H2,(H,12,13)/p-1/t2-,3+/m0/s1


Unification Links: ChEBI:57441, ChemSpider:20015966, HMDB:HMDB05971, IAF1260:45750, KEGG:C04575, MetaboLights:MTBLC57441, PubChem:21145097

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -176.11424Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

L-ascorbate degradation II (bacterial, aerobic) :
3-keto-L-gulonate + NAD+2,3-dioxo-L-gulonate + NADH + H+

L-ascorbate degradation V :
2,3-dioxo-L-gulonate → 2-carboxy-L-xylonolactone

Reactions known to produce the compound:

L-ascorbate degradation II (bacterial, aerobic) , L-ascorbate degradation V :
dehydroascorbate (bicyclic form) → 2,3-dioxo-L-gulonate + H+

In Reactions of unknown directionality:

Not in pathways:
3-keto-L-gulonate + NAD(P)+ = 2,3-dioxo-L-gulonate + NAD(P)H + H+

In Transport reactions:
Na+[periplasm] + 2,3-dioxo-L-gulonate[periplasm] → Na+[cytosol] + 2,3-dioxo-L-gulonate[cytosol]

This compound has been characterized as an alternative substrate of the following enzymes: β-keto-L-gulonic acid decarboxylase


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
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