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MetaCyc Compound: cis-aconitate

Synonyms: (Z)-prop-1-ene-1,2,3-tricarboxylate, cis-aconitic acid

Superclasses: an acid all carboxy acids a carboxylate a tricarboxylate

Summary:
cis-aconitate is named after the plant Aconitum napellus, from which it was first isolated in 1828 [Peschier28]. The plants of the genus Aconitum (family of the Ranunculaceae) are famous for the many alkaloids they contain [Pictet04].

Chemical Formula: C6H3O6

Molecular Weight: 171.09 Daltons

Monoisotopic Molecular Weight: 174.0164379252 Daltons

<i>cis</i>-aconitate compound structure

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

InChI: InChI=1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)/p-3/b3-1-

InChIKey: InChIKey=GTZCVFVGUGFEME-IWQZZHSRSA-K

Unification Links: CAS:585-84-2 , ChEBI:16383 , ChemSpider:4573582 , HMDB:HMDB00072 , IAF1260:34920 , KEGG:C00417 , KNApSAcK:C00001177 , MetaboLights:MTBLC16383 , PubChem:5459816

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -191.19519 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

itaconate biosynthesis :
cis-aconitate + H+ → CO2 + itaconate

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

Not in pathways:
an acyl-protein synthetase + a carboxylate + ATP → an acyl-protein thioester + AMP + diphosphate
a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate

Reactions known to produce the compound:

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[periplasmic space] + H2O[periplasmic space]a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
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 aldehyde + FMNH2 + oxygen → hν + a carboxylate + FMN + H2O + 2 H+
an acylcholine + H2O → choline + a carboxylate + H+
a 1,2-diacyl-3-β-D-galactosyl-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:

ethylene biosynthesis V (engineered) :
citrate ↔ cis-aconitate + H2O
cis-aconitate + H2O ↔ D-threo-isocitrate

glyoxylate cycle :
citrate ↔ cis-aconitate + H2O
cis-aconitate + H2O ↔ D-threo-isocitrate

itaconate biosynthesis :
citrate ↔ cis-aconitate + H2O

L-glutamine biosynthesis III :
citrate ↔ cis-aconitate + H2O
cis-aconitate + H2O ↔ D-threo-isocitrate

methylaspartate cycle :
citrate ↔ cis-aconitate + H2O
cis-aconitate + H2O ↔ D-threo-isocitrate

mixed acid fermentation :
citrate ↔ cis-aconitate + H2O
cis-aconitate + H2O ↔ D-threo-isocitrate

reductive TCA cycle I :
citrate ↔ cis-aconitate + H2O
cis-aconitate + H2O ↔ D-threo-isocitrate

reductive TCA cycle II :
citrate ↔ cis-aconitate + H2O
cis-aconitate + H2O ↔ D-threo-isocitrate

TCA cycle I (prokaryotic) :
citrate ↔ cis-aconitate + H2O
cis-aconitate + H2O ↔ D-threo-isocitrate

TCA cycle II (plants and fungi) :
citrate ↔ cis-aconitate + H2O
cis-aconitate + H2O ↔ D-threo-isocitrate

TCA cycle III (animals) :
citrate ↔ cis-aconitate + H2O
cis-aconitate + H2O ↔ D-threo-isocitrate

TCA cycle IV (2-oxoglutarate decarboxylase) :
citrate ↔ cis-aconitate + H2O
cis-aconitate + H2O ↔ D-threo-isocitrate

TCA cycle V (2-oxoglutarate:ferredoxin oxidoreductase) :
citrate ↔ cis-aconitate + H2O
cis-aconitate + H2O ↔ D-threo-isocitrate

In Reactions of unknown directionality:

Not in pathways:
trans-aconitate = cis-aconitate

Not in pathways:
eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a 2-acyl 1-lyso-phosphatidylcholine[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
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[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
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 unknown oxidized electron acceptor + H2O = a carboxylate + an unknown reduced 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 + H2O = a carboxylate + 2 a reduced ferredoxin + 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

Enzymes inhibited by cis-aconitate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: prephenate dehydratase [Baldwin83]

Inhibitor (Mechanism unknown) of: isocitrate lyase

This compound has been characterized as an alternative substrate of the following enzymes: citryl-CoA synthetase , 2-methylcitrate dehydratase , trans-aconitate 2-methyltransferase , 2-methylcitrate dehydratase , 2-methylcitrate dehydratase


References

Baldwin83: Baldwin GS, Davidson BE (1983). "Kinetic studies on the mechanism of chorismate mutase/prephenate dehydratase from Escherichia coli K12." Biochim Biophys Acta 1983;742(2);374-83. PMID: 6337635

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

Peschier28: Peschier (1828). Trommsdorf's Journal der Pharmacie, 5,I, 93; 8, I, 266.

Pictet04: Pictet, A. (1904). "The Vegetable Alkaloids: With Particular Reference to Their Chemical constitution." Translated by H.C. Biddler, Published by J. Wiley & Sons London 1913.


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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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