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discounted EARLY registration ends Dec 31, 2014
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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
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MetaCyc Compound: N-ethylmaleimide

Synonyms: ethylmaleimide, maleic acid N-ethylimide, maleimide, N-ethyl-, N-EM, 1H-pyrrole-2,5-dione, 1-ethyl-

Chemical Formula: C6H7NO2

Molecular Weight: 125.13 Daltons

Monoisotopic Molecular Weight: 125.0476784741 Daltons

SMILES: CCN1(C(=O)C=CC(=O)1)

InChI: InChI=1S/C6H7NO2/c1-2-7-5(8)3-4-6(7)9/h3-4H,2H2,1H3

InChIKey: InChIKey=HDFGOPSGAURCEO-UHFFFAOYSA-N

Unification Links: ChEBI:44485 , ChemSpider:4209 , DrugBank:DB02967 , KEGG:C02441 , PubChem:4362

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 31.287842 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

Not in pathways:
N-ethylmaleimide + NADPH + H+ → N-ethylsuccinimide + NADP+

Enzymes activated by N-ethylmaleimide, sorted by the type of activation, are:

Activator (Allosteric) of: malonyl-CoA:shisonin 6-O-malonyltransferase [Suzuki01b]

Activator (Mechanism unknown) of: 2,3,4-saturated fatty acyl-[acp]:NAD+ oxidoreductase [Weeks68]

Enzymes inhibited by N-ethylmaleimide, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: arylamine N-acetyltransferase [Yamamura00, Comment 1]

Inhibitor (Uncompetitive) of: diamine oxidase [Suzuki96]

Inhibitor (Noncompetitive) of: aspartate semialdehyde dehydrogenase [Hegeman70, Helmward89]

Inhibitor (Irreversible) of: pyruvate oxidase [Koland82] , S-adenosylhomocysteine hydrolase [Guranowski77a]

Inhibitor (Allosteric) of: butein 4'-glucosyltransferase [Stich94]

Inhibitor (Mechanism unknown) of: 13-hydroxylupanine O-tigloyltransferase [Suzuki94] , malonyl-CoA-ACP transacylase [Ruch73] , acetyl-CoA:ACP transacylase [Lowe88] , glucosamine-1-phosphate acetyltransferase [Pompeo98] , NADPH-dependent curcumin reductase [Hassaninasab11] , UDP-3-O-acyl-N-acetylglucosamine deacetylase [Anderson88a] , tRNA-guanine transglycosylase [Garcia97] , prephenate dehydratase [Ma85] , sorbitol-6-phosphate dehydrogenase [Novotny84] , spermidine synthase [Bowman73] , 4-aminobutyrate transaminase [Schulz90] , thiamin monophosphate kinase [Nishino72] , S-formylglutathione hydrolase [Gonzalez06a] , cyclopropane fatty acyl phospholipid synthase [Taylor79, Grogan97] , S-formylglutathione hydrolase [Gonzalez06a] , glyoxalase [Misra95, Comment 2] , glycerol dehydrogenase [Tang79] , 2-keto-4-hydroxyglutarate aldolase [Comment 3] , 3-ketoacyl-CoA thiolase [Pawar81] , FMN reductase [Fontecave87] , 2,3-dihydroxybenzoate-AMP ligase [Bryce72] , L-seryl-AMP synthase [Bryce72] , quercetin 7-O-glucosyltransferase [Stich] , cyanidin 3-O-glucoside 6"-O-rhamnosyltransferase [Kamsteeg80] , delphinidin 3-O-glucoside 6"-O-rhamnosyltransferase [Kamsteeg80] , cyanidin 3-O-glucoside 6"-O-malonyltransferase [Suzuki03] , cystathionine γ-lyase [Matsuo59] , NAD+-dependent malate dehydrogenase [Kiick84] , D-octopine synthase [Sheikh93] , D-arabinose dehydrogenase [Kim98c] , kaempferide 3-O-glucosyltransferase (F3GT2) [Ishikura94] , kaempferide 3-O-glucosyltransferase (F3GT1) [Ishikura94] , pheophorbide demethoxycarbonylase [Suzuki02d] , 3,6,7,2',4'-pentamethylquercetagetin 3'-O-glucosyltransferase [Bajaj83] , 2'-hydroxy 3,6,7,4'-tetramethylquercetagetin 3'-O-glucosyltransferase [Bajaj83] , 3,6,7,4'-tetramethylquercetagetin 3'-O-glucosyltransferase [Bajaj83] , 3,7,4'-trimethylquercetagetin 3'-O-glucosyltransferase [Bajaj83] , 2'-hydroxy 3,7,3',4'-tetramethylquercetin 2'-O-glucosyltransferase [Bajaj83] , 2'-hydroxy 3,7,4'-trimethylquercetin 2'-O-glucosyltransferase [Bajaj83] , 2'-hydroxy 3,6,7,4'-tetramethylquercetagetin 3'-O-glucoside 2'-O-methyltransferase [Khouri86] , 3,7,4'trimethylquercetin 2'-O-glucoside 3'-O-methyltransferase [Khouri86] , 3-O-methylquercetin 7-O-methyltransferase [Khouri88] , 3,7-dimethylquercetagetin 4'-O-methyltransferase [De85] , 3,7-dimethylquercetin 4'-O-methyltransferase [De85] , quercetin 3-O-methyltransferase [De85] , squalene-hopene cyclase [Seckler86] , potchoulol synthase [Munck90] , 4-oxalocrotonate decarboxylase [Orii06] , 2-hydroxymuconate 6-semialdehyde dehydrogenase [Orii06] , N-acetylglucosamine-6-phosphate deacetylase [Yamano96] , N-cyclohexylformamide hydratase [Goda01] , N-benzylformamide deformylase [Fukatsu04] , carboxynorspermidine dehydrogenase [Nakao91] , glycocholate hydrolase [Tanaka00] , D-galacturonate dehydrogenase [Wagner76] , galactonolactonase [Ishikawa08] , L-galactono-γ-lactone dehydrogenase [Shigeoka79] , β-alanine amide amidase [Komeda04] , [thyroglobulin]-3,5-diiodotyrosine synthase [Coval67] , cytidine 5'-monophosphate N-acetylneuraminate synthetase [RodriguezAparic92] , N-acetylneuraminate 9-phosphate synthase [Chen02d] , carnitine-acylcarnitine translocase [Indiveri98] , V-type Na+-translocating ATPase [Murata01] , sterigmatocystin O-methyltransferase [Liu99b] , 6-demethylsterigmatocystin O-methyltransferase [Yabe89] , dimethylmaleate hydratase [KollmannKoch84] , deacetoxycephalosporin C hydroxylase [Baker91] , deacetoxycephalosporin C synthase [Dotzlaf89] , deacetoxycephalosporin C synthase [Dotzlaf87, Baldwin87] , isopenicillin N synthase [Perry88] , isopenicillin N epimerase [Usui89] , isopenicillin N epimerase [Laiz90] , L-lysine ε-dehydrogenase [Misono89] , phosphatidate phosphatase [Pierrugues01] , rubredoxin NAD+ reductase [Petitdemange79] , phloroglucinol reductase [Haddock89] , cysteine-S-conjugate N-acetyltransferase [Aigner96] , 2,4-diaminopentanoate dehydrogenase [Somack73] , 4-carboxy-2-hydroxymuconate-6-semialdehyde dehydrogenase [Maruyama78] , 4-oxalocitramalate aldolase [Hara03] , β-cyano-L-alanine hydratase [Piotrowski01] , β-cyano-L-alanine nitrilase [Piotrowski01] , dolichyl-phosphate mannose synthase [Haselbeck89] , acetyl-CoA:13-[O(2')-β-D-glucopyranosyl-β-D-glucopyranosyloxy]docosanoate acetyltransferase [Bucholtz76] , 2-amino-4-oxopentanoate thiolase [Jeng74, Comment 4] , 13-sophorosyloxydocosanoate 6',6''-diacetate acetylesterase [Bucholtz76a] , 6-hydroxymellein synthase [Kurosaki93] , NADP+-benzaldehyde dehydrogenase [Stachow67] , phosphatidate phosphatase [Pierrugues01] , haloalkane dehalogenase [Keuning85] , arginine deiminase [Monstadt91] , benzyl alcohol dehydrogenase [Shaw90] , 2-pyrone-4,6-dicarboxylate hydrolase [Masai99a] , NAD-dependent formate dehydrogenase [Asano88] , glycerol dehydrogenase [McGregor74] , methionine γ-lyase [Esaki87] , ethanolamine kinase [Wharfe79] , D-carnitine dehydrogenase [Setyahadi97] , D-ornithine aminomutase [Somack73a] , hydroxymethylglutaryl-CoA synthase [Middleton72] , 3-aminopropionaldehyde dehydrogenase [Awal95] , 4-coumaroyl-CoA:pelargonidin-3-O-β-D-glucoside-6''-O-acyltransferase [YonekuraSakakib00] , isoliquiritigenin 4'-glucosyltransferase [Stich94] , butein 4'-glucosyltransferase [Halbwirth97] , sulfuretin 4'-glucosyltransferase [Halbwirth97] , 2,5-dihydroxypyridine dioxygenase [Gauthier71] , nicotinate dehydrogenase [Hurh94] , ferrochelatase [Dailey86a] , uroporphyrinogen decarboxylase [Jones93] , porphobilinogen deaminase [Jordan73] , canaline reductase [Rosenthal92] , spermine synthase [Raina83] , Δ1-pyrroline-3-hydroxy-5-carboxylate dehydrogenase [Adams60] , 4-hydroxyglutamate transaminase [GOLDSTONE62] , hydroxyproline 2-epimerase [Adams64] , caffeoyl-CoA:pelargonidin-3-O-β-D-glucoside-6''-O-acyltransferase [YonekuraSakakib00] , 4-coumaroyl-CoA:cyanidin-3,5-diglucoside-6''-O-acyltransferase [YonekuraSakakib00] , 4-coumaroyl-CoA:cyanidin-3-O-β-D-glucoside-6''-O-acyltransferase [YonekuraSakakib00] , glucosamine 6-phosphate isomerase [Steimle97] , L-sorbosone dehydrogenase [Asakura99] , anthocyanidin-3-O-glucoside-6"-O-malonyltransferase [Suzuki02c] , pelargonidin-3-O-glucoside-6''-O-rhamnosyltransferase [Kamsteeg80] , maleylacetoacetate isomerase [Seltzer73] , caffeoyl-CoA:pelargonidin-3,5-diglucoside-6''-O-acyltransferase [YonekuraSakakib00] , malonyl-CoA:pelargonidin-3-O-(6-caffeoyl-β-D-glucoside)-5-O-β-D-glucoside 6-O-malonyltransferase [Suzuki01b] , anthocyanin 5-O-glucoside-4'''-O-malonyltransferase [Suzuki04a] , L-3-aminobutyryl coenzyme A deaminase [Jeng74a] , ethylnitronate monooxygenase [Kido76] , nitroalkane oxidase [Kido78]

Inhibitor (Other types) of: indole-3-carboxylate decarboxylase [Yoshida02b] , benzoate 4-monooxygenase [Reddy75] , [acyl carrier protein] S-malonyltransferase [Hoenke99] , L-sorbosone dehydrogenase [Hoshino91] , glutamate dehydrogenase [Blumenthal73] , lactaldehyde dehydrogenase [Grochowski06] , isobutyryl-CoA:FAD oxidoreductase [Ikeda83] , indole-3-acetaldoxime dehydratase [Shukla68] , sulfite dehydrogenase [Nakamura95] , sulfur oxygenase reductase [Kletzin89] , methylglyoxal reductase (NADH-dependent) [TING65]


References

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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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