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Escherichia coli K-12 substr. MG1655 Compound: fumarate

Synonyms: fum, fumaric acid

Superclasses: an acid all carboxy acids a carboxylate a dicarboxylate a C4-dicarboxylate

Chemical Formula: C4H2O4

Molecular Weight: 114.06 Daltons

Monoisotopic Molecular Weight: 116.0109586168 Daltons

fumarate compound structure

SMILES: C(C([O-])=O)=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-OWOJBTEDSA-L

Unification Links: CAS:110-17-8 , ChEBI:29806 , ChemSpider:4573886 , DrugBank:DB01677 , HMDB:HMDB00134 , IAF1260:33938 , KEGG:C00122 , KNApSAcK:C00001183 , MetaboLights:MTBLC29806 , PubChem:5460307

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -143.7

Reactions known to consume the compound:

Not in pathways:
L-aspartate + fumarate → 2-iminosuccinate + succinate + H+

Reactions known to produce the compound:

adenosine ribonucleotides de novo biosynthesis :
adenylo-succinate → fumarate + AMP

cinnamate and 3-hydroxycinnamate degradation to 2-oxopent-4-enoate :
(2Z,4E,7E)-2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate + H2O → (2Z)-2-hydroxypenta-2,4-dienoate + fumarate + H+

inosine-5'-phosphate biosynthesis I :
5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole → fumarate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide

succinate to cytochrome bd oxidase electron transfer , succinate to cytochrome bo oxidase electron transfer , TCA cycle I (prokaryotic) :
succinate + a ubiquinone[inner membrane]fumarate + an ubiquinol[inner membrane]

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+

Reactions known to both consume and produce the compound:

glycerol-3-phosphate to fumarate electron transfer , hydrogen to fumarate electron transfer , NADH to fumarate electron transfer :
fumarate + a menaquinol[inner membrane] ↔ succinate + a menaquinone[inner membrane]

L-arginine biosynthesis I (via L-ornithine) :
L-arginino-succinate ↔ L-arginine + fumarate

L-glutamate degradation II :
L-aspartate ↔ ammonium + fumarate

mixed acid fermentation :
(S)-malate ↔ fumarate + H2O
fumarate + a menaquinol[inner membrane] ↔ succinate + a menaquinone[inner membrane]

TCA cycle I (prokaryotic) :
(S)-malate ↔ fumarate + H2O

In Reactions of unknown directionality:

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

In Transport reactions:
fumarate[periplasmic space] + 2 H+[periplasmic space]fumarate[cytosol] + 2 H+[cytosol] ,
succinate[cytosol] + fumarate[periplasmic space]fumarate[cytosol] + succinate[periplasmic space] ,
fumarate[periplasmic space]fumarate[cytosol] ,
a C4-dicarboxylate[periplasmic space] + 2 H+[periplasmic space]a C4-dicarboxylate[cytosol] + 2 H+[cytosol] ,
a C4-dicarboxylate[periplasmic space] + 3 H+[periplasmic space]a C4-dicarboxylate[cytosol] + 3 H+[cytosol]

In Redox half-reactions:
fumarate[in] + 2 H+[in] + 2 e-[membrane] → succinate[in]

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

Inhibitor (Competitive) of: glutamate decarboxylase B [Fonda72] , glutamate decarboxylase A [Fonda72]

Inhibitor (Mechanism unknown) of: malate dehydrogenase [Bologna07]

This compound has been characterized as an alternative substrate of the following enzymes: L-aspartate oxidase

In Growth Media: PMA carbon source test + fumarate


References

Bologna07: Bologna FP, Andreo CS, Drincovich MF (2007). "Escherichia coli malic enzymes: two isoforms with substantial differences in kinetic properties, metabolic regulation, and structure." J Bacteriol 189(16);5937-46. PMID: 17557829

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


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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by SRI International Pathway Tools version 19.0 on Fri Jul 31, 2015, BIOCYC14B.