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MetaCyc Compound Class: D-fructuronate

Synonyms: fructuronate

Superclasses: an acidall carboxy acidsa carboxylatea monocarboxylatea uronatea hexuronate

D-fructuronate compound structure

Chemical Formula: C6H9O7

Child Classes: D-fructofuranuronate (2)

Citations: [Hickman60]

Molecular Weight: 193.13 Daltons

Monoisotopic Molecular Weight: 194.0426526757 Daltons

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

Unification Links: ChEBI:4126, IAF1260:36345, KEGG:C00905, PubChem:439343

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -168.512Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

Not in pathways:
D-mannonate + NADP+D-fructuronate + NADPH + H+

methyl ketone biosynthesis :
a carboxylate + ATP + coenzyme A → an acyl-CoA + AMP + diphosphate

Not in pathways:
a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate

Reactions known to produce the compound:

myo-inositol degradation II , pectin degradation III :
D-tagaturonate → D-fructuronate

3,3'-thiodipropanoate degradation :
3-sulfinopropionate + an acyl-CoA → 3-sulfinopropanoyl-CoA + a carboxylate

dimethylsulfoniopropanoate degradation II (cleavage) :
dimethylsulfoniopropanoate + an acyl-CoA → dimethylsulfoniopropioyl-CoA + a carboxylate

NAD/NADP-NADH/NADPH mitochondrial interconversion (yeast) :
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+
an aldehyde + NAD+ + H2O → a carboxylate + NADH + 2 H+

phosphatidylcholine resynthesis via glycerophosphocholine :
a phosphatidylcholine + 2 H2O → sn-glycero-3-phosphocholine + 2 a carboxylate + 2 H+

Not in pathways:
a 1-acyl 2-lyso-phosphatidylcholine[periplasm] + H2O[periplasm]a carboxylate[periplasm] + sn-glycero-3-phosphocholine[periplasm] + H+[periplasm]
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
an L-1-phosphatidyl-inositol + H2O → a 1-acyl-sn-glycero-3-phospho-D-myo-inositol + a carboxylate + H+
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an aldehyde + oxygen + H2O → a carboxylate + hydrogen peroxide + H+
an acylcholine + H2O → choline + a carboxylate + H+
a 1,2-diacyl-3-O-(β-D-galactopyranosyl)-sn-glycerol + 2 H2O → 2 a carboxylate + 3-β-D-galactosyl-sn-glycerol + 2 H+
an acyl phosphate + H2O → a carboxylate + phosphate + H+
an S-acylglutathione + H2O → a carboxylate + glutathione
an N-acyl-L-aspartate + H2O → L-aspartate + a carboxylate

Reactions known to both consume and produce the compound:

β-D-glucuronide and D-glucuronate degradation :
aldehydo-D-glucuronate ↔ D-fructuronate

D-fructuronate degradation :
D-mannonate + NAD+D-fructuronate + NADH + H+

sphingolipid recycling and degradation (yeast) :
a dihydroceramide + H2O ↔ D-erythro-sphinganine + a carboxylate

In Reactions of unknown directionality:

L-gulonate degradation :
L-gulonate + NAD+ = D-fructuronate + NADH + H+

Not in pathways:
a monocarboxylic acid amide + H2O = a monocarboxylate + ammonium

Not in pathways:
eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a 2-acyl 1-lyso-phosphatidylcholine[periplasm] + H2O[periplasm] = a carboxylate[periplasm] + sn-glycero-3-phosphocholine[periplasm] + H+[periplasm]
an aldehyde + an electron-transfer quinone + H2O = a carboxylate + an electron-transfer quinol + H+
a triacyl-sn-glycerol + H2O = a 1,2-diacyl-sn-glycerol + a carboxylate + H+
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasm] + FAD[periplasm] + H2O[periplasm] = a carboxylate[periplasm] + FADH2[periplasm]
a nitrile + 2 H2O = a carboxylate + ammonium
an aliphatic nitrile + 2 H2O = a carboxylate + ammonium
an N-acyl-L-homoserine lactone + H2O = L-homoserine lactone + a carboxylate
an aldehyde + an oxidized unknown electron acceptor + H2O = a carboxylate + an reduced unknown electron acceptor + H+
an N-acylated aromatic-L-amino acid + H2O = a carboxylate + an aromatic L-amino acid
an N-acylated-D-amino acid + H2O = a D-amino acid + a carboxylate
an N-acylated aliphatic-L-amino acid + H2O = a carboxylate + an aliphatic L-amino acid
a D-hexose + an acyl phosphate = a D-hexose-phosphate + a carboxylate
an aldehyde + 2 an oxidized ferredoxin [iron-sulfur] cluster + H2O = a carboxylate + 2 a reduced ferredoxin [iron-sulfur] cluster + 3 H+
an aldehyde + NAD(P)+ + H2O = a carboxylate + NAD(P)H + 2 H+
an N-acyl-D-glutamate + H2O = a carboxylate + D-glutamate
an anilide + H2O = aniline + a carboxylate + H+
a 5'-acylphosphoadenosine + H2O = a carboxylate + AMP + 2 H+
a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H+
an N6acyl-L-lysine + H2O = a carboxylate + L-lysine
an N-acyl-D-aspartate + H2O = a carboxylate + D-aspartate

In Transport reactions:
D-fructuronate[periplasm] + H+[periplasm]D-fructuronate[cytosol] + H+[cytosol]

Enzymes inhibited by D-fructuronate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: altronate oxidoreductase [Portalier72a, Comment 1]

Credits:
Revised 28-Jul-2010 by Caspi R, SRI International


References

Hickman60: Hickman, J., Ashwell, G. (1960). "Uronic Acid Metabolism in Bacteria: II. Purification and properties of D-altronic acid and D-mannonic acid dehydrogenases in Escherichia coli." J. Biol. Chem. 235:1566-1570.

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

Portalier72a: Portalier RC (1972). "[D-altronate: NAD-oxidoreductase from Escherichia coli K12. Kinetic studies]." Eur J Biochem 1972;30(2);211-9. PMID: 4351434

Portalier72b: Portalier RC, Stoeber FR (1972). "[D-altronate: NAD-oxidoreductase in Escherichia coli K12. Purification, properties, and specificity]." Eur J Biochem 1972;26(1);50-61. PMID: 4402917


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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 Pathway Tools version 19.5 (software by SRI International) on Wed May 4, 2016, biocyc13.