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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

InChIKey: InChIKey=GJQWCDSAOUMKSE-STHAYSLISA-M

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): -176.11424 Inferred 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+[periplasmic space] + 2,3-dioxo-L-gulonate[periplasmic space] → 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


References

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


Report Errors or Provide Feedback
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 Tue Sep 1, 2015, biocyc11.