Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store

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-


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]


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

Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by Pathway Tools version 19.5 (software by SRI International) on Sat Feb 13, 2016, biocyc13.