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Escherichia coli K-12 substr. MG1655 Compound: maleate

Synonyms: maleic acid, cis-butenedioic acid

Superclasses: an acidall carboxy acidsa carboxylatea dicarboxylatea C4-dicarboxylate

Chemical Formula: C4H2O4

Molecular Weight: 114.06 Daltons

Monoisotopic Molecular Weight: 116.0109586168 Daltons

maleate compound structure

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

InChI: InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/p-2/b2-1-

InChIKey: InChIKey=VZCYOOQTPOCHFL-UPHRSURJSA-L

Unification Links: CAS:110-16-7, ChEBI:30780, ChemSpider:4450430, HMDB:HMDB00176, KEGG:C01384, PubChem:5288227

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -144.41

Reactions known to produce the compound:

Not in pathways:
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+
an acyl phosphate + H2O → a carboxylate + phosphate + H+
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
a 1-acyl 2-lyso-phosphatidylcholine + H2O → a carboxylate + sn-glycero-3-phosphocholine + H+

In Reactions of unknown directionality:

Not in pathways:
a 2-acyl 1-lyso-phosphatidylcholine + H2O = a carboxylate + sn-glycero-3-phosphocholine + H+
an aldehyde[periplasm] + FAD[periplasm] + H2O[periplasm] = a carboxylate[periplasm] + FADH2[periplasm]

In Transport reactions:
a C4-dicarboxylate[periplasm]a C4-dicarboxylate[extracellular space],
a C4-dicarboxylate[periplasm] + 2 H+[periplasm]a C4-dicarboxylate[cytosol] + 2 H+[cytosol],
a C4-dicarboxylate[periplasm] + 3 H+[periplasm]a C4-dicarboxylate[cytosol] + 3 H+[cytosol]

Enzymes inhibited by maleate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: phosphoribosylaminoimidazole-succinocarboxamide synthase [Nelson05], glutamate decarboxylase B [Fonda72], aspartate transaminase [Miyahara94], glutamate decarboxylase A [Fonda72], kynurenine-oxoglutarate transaminase [Miyahara94], phenylalanine transaminase [Miyahara94]

References

Fonda72: Fonda ML (1972). "Glutamate decarboxylase. Substrate specificity and inhibition by carboxylic acids." Biochemistry 1972;11(7);1304-9. PMID: 4552052

Miyahara94: Miyahara I, Hirotsu K, Hayashi H, Kagamiyama H (1994). "X-ray crystallographic study of pyridoxamine 5'-phosphate-type aspartate aminotransferases from Escherichia coli in three forms." J Biochem (Tokyo) 116(5);1001-12. PMID: 7896726

Nelson05: Nelson SW, Binkowski DJ, Honzatko RB, Fromm HJ (2005). "Mechanism of action of Escherichia coli phosphoribosylaminoimidazolesuccinocarboxamide synthetase." Biochemistry 44(2);766-74. PMID: 15641804


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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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