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

Synonyms: iodoacetoamide, 2-iodoacetamide, acetamide, 2-iodo-, monoiodoacetamide, surauto, N-(3-methoxy-4-butoxybenzyl)thiobarbituric acid

Superclasses: an organohalogen compound an organoiodine compound

Chemical Formula: C2H4NOI

Molecular Weight: 184.96 Daltons

Monoisotopic Molecular Weight: 184.9337567557 Daltons

SMILES: C(I)C(N)=O

InChI: InChI=1S/C2H4INO/c3-1-2(4)5/h1H2,(H2,4,5)

InChIKey: InChIKey=PGLTVOMIXTUURA-UHFFFAOYSA-N

Unification Links: ChEBI:103838 , ChemSpider:3596 , PubChem:3727

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 2.0444808 Inferred by computational analysis [Latendresse13]

Enzymes activated by iodoacetamide, sorted by the type of activation, are:

Activator (Allosteric) of: histamine N-methyltransferase [Harvima85]

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

Inhibitor (Irreversible) of: L-glutamine:D-fructose-6-phosphate aminotransferase [Badet87] , L-glutamate γ-semialdehyde dehydrogenase [ForteMcRobbie86]

Inhibitor (Mechanism unknown) of: malonyl-CoA-ACP transacylase [Ruch73] , acetyl-CoA:ACP transacylase [Lowe88] , farnesyl diphosphate synthase [Fujisaki86] , geranyl diphosphate synthase [Fujisaki86] , isopentenyl diphosphate isomerase [Fujisaki86, Comment 1] , glucosamine-1-phosphate acetyltransferase [Pompeo98] , homoserine O-succinyltransferase [Born99, Comment 2] , amidophosphoribosyl transferase [Messenger79] , formate dehydrogenase-N , 3-ketoacyl-CoA thiolase [Yang83] , glutathionylspermidine amidase [Lin97] , β-ketoacyl-ACP synthase [Greenspan69, Comment 3] , acetoacetyl-[acp] synthase [Greenspan69, Comment 3] , acyl-CoA thioesterase [Naggert91] , 6-methylsalicylate synthase [Child98] , genistein 4'-O-methyltransferase [Curir03] , apigenin 4'-O-methyltransferase [Curir03] , kaempferol 4'-O-methyltransferase [Curir03] , coniine methyltransferase [Roberts74] , 2-protocatechuoylphloroglucinolcarboxylate esterase [Child63] , carboxynorspermidine dehydrogenase [Nakao91] , 5-dehydro-4-deoxy-D-glucarate dehydratase [Dagley75] , cholesterol 7α-hydroxylase [Ogishima87] , sterigmatocystin O-methyltransferase [Liu99] , hydantoin racemase [Wiese00] , loganic acid O-methyltransferase [Madyastha73] , desoxyhemigossypol-6-O-methyltransferase [Liu99a] , isopenicillin N epimerase [Usui89] , isopenicillin N epimerase [Laiz90] , proline racemase [Cardinale68] , β-ureidopropionase [Walsh01] , butyrate kinase [Comment 4] , 2-(2'-methylthio)ethylmalate synthase [Textor04] , acetyl-CoA:13-[O(2')-β-D-glucopyranosyl-β-D-glucopyranosyloxy]docosanoate acetyltransferase [Bucholtz76] , glyceraldehyde 3-phosphate dehydrogenase [Krishnan90] , 6-hydroxymellein synthase [Kurosaki93] , haloalkane dehalogenase [Keuning85] , glycerol dehydrogenase [McGregor74] , tryptophan 2-monooxygenase [Kosuge66] , ethanolamine kinase [Wharfe79] , acetyl-CoA acetyltransferase [Wiesenborn88] , ferrochelatase [Dailey86] , uroporphyrinogen decarboxylase [Jones93] , agmatine deiminase [Nakada03] , N-carbamoylputrescine amidohydrolase [Nakada03] , glucosamine 6-phosphate isomerase [Steimle97] , L-3-aminobutyryl coenzyme A deaminase [Jeng74] , L-asparaginase [Raha90]

Inhibitor (Other types) of: methylglutamate dehydrogenase [Bamforth77] , fluoroacetaldehyde dehydrogenase [Murphy01] , D-proline dehydrogenase [Tanigawa10] , D-amino acid dehydrogenase [Tanigawa10] , 2-phosphinomethylmalate synthase [Shimotohno88] , (R)-citramalyl-CoA lyase [Friedmann07] , malonyl-CoA reductase [Alber06] , lactaldehyde dehydrogenase [Grochowski06]


References

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Badet87: Badet B, Vermoote P, Haumont PY, Lederer F, LeGoffic F (1987). "Glucosamine synthetase from Escherichia coli: purification, properties, and glutamine-utilizing site location." Biochemistry 1987;26(7);1940-8. PMID: 3297136

Bamforth77: Bamforth CW, Large PJ (1977). "Solubilization, partial purification and properties of N-methylglutamate dehydrogenase from Pseudomonas aminovorans." Biochem J 161(2);357-70. PMID: 15545

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ForteMcRobbie86: Forte-McRobbie CM, Pietruszko R (1986). "Purification and characterization of human liver "high Km" aldehyde dehydrogenase and its identification as glutamic gamma-semialdehyde dehydrogenase." J Biol Chem 261(5);2154-63. PMID: 3944130

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Fujisaki86: Fujisaki S, Nishino T, Katsuki H (1986). "Isoprenoid synthesis in Escherichia coli. Separation and partial purification of four enzymes involved in the synthesis." J Biochem (Tokyo) 1986;99(5);1327-37. PMID: 3519603

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Grochowski06: Grochowski LL, Xu H, White RH (2006). "Identification of lactaldehyde dehydrogenase in Methanocaldococcus jannaschii and its involvement in production of lactate for F420 biosynthesis." J Bacteriol 188(8);2836-44. PMID: 16585745

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Keuning85: Keuning S, Janssen DB, Witholt B (1985). "Purification and characterization of hydrolytic haloalkane dehalogenase from Xanthobacter autotrophicus GJ10." J Bacteriol 1985;163(2);635-9. PMID: 4019411

Kosuge66: Kosuge T, Heskett MG, Wilson EE (1966). "Microbial synthesis and degradation of indole-3-acetic acid. I. The conversion of L-tryptophan to indole-3-acetamide by an enzyme system from Pseudomonas savastanoi." J Biol Chem 241(16);3738-44. PMID: 5916389

Krishnan90: Krishnan G, Altekar W (1990). "Characterization of a halophilic glyceraldehyde-3-phosphate dehydrogenase from the archaebacterium Haloarcula vallismortis." J. Gen. Appl. Microbiol. 36:19-32.

Kurosaki93: Kurosaki F, Itoh M, Kizawa Y, Nishi A (1993). "Partial purification and characterization of a polyketide biosynthetic enzyme, 6-hydroxymellein synthase, in elicitor-treated carrot cell extracts." Arch Biochem Biophys 300(1);157-63. PMID: 8424647

Laiz90: Laiz L, Liras P, Castro JM, Martin JF (1990). "Purification and characterization of the isopenicillin N epimerase from Nocardia lactamdurans." Journal of General Microbiology 136, 663-671.

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

Lin97: Lin CH, Kwon DS, Bollinger JM, Walsh CT (1997). "Evidence for a glutathionyl-enzyme intermediate in the amidase activity of the bifunctional glutathionylspermidine synthetase/amidase from Escherichia coli." Biochemistry 36(48);14930-8. PMID: 9398217

Liu99: Liu BH, Bhatnagar D, Chu FS (1999). "Purification and characterization of 40-kDa sterigmatocystin O-methyltransferase involved in aflatoxin biosynthesis." Nat Toxins 7(2);63-9. PMID: 10495468

Liu99a: Liu J, Benedict CR, Stipanovic RD, Bell AA (1999). "Purification and Characterization of S-Adenosyl-L-Methionine: Desoxyhemigossypol-6-O-Methyltransferase from Cotton Plants. An Enzyme Capable of Methylating the Defense Terpenoids of Cotton." Plant Physiol 121(3);1017-1024. PMID: 10557251

Lowe88: Lowe PN, Rhodes S (1988). "Purification and characterization of [acyl-carrier-protein] acetyltransferase from Escherichia coli." Biochem J 1988;250(3);789-96. PMID: 3291856

Madyastha73: Madyastha KM, Guarnaccia R, Baxter C, Coscia CJ (1973). "S-Adenosyl-L-methionine: loganic acid methyltransferase. A carboxyl-alkylating enzyme from Vinca rosea." J Biol Chem 248(7);2497-501. PMID: 4698228

McGregor74: McGregor WG, Phillips J, Suelter CH (1974). "Purification and kinetic characterization of a monovalent cation-activated glycerol dehydrogenase from Aerobacter aerogenes." J Biol Chem 249(10);3132-9. PMID: 4364415

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Murphy01: Murphy CD, Moss SJ, O'Hagan D (2001). "Isolation of an aldehyde dehydrogenase involved in the oxidation of fluoroacetaldehyde to fluoroacetate in Streptomyces cattleya." Appl Environ Microbiol 67(10);4919-21. PMID: 11571203

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Nakao91: Nakao H, Shinoda S, Yamamoto S (1991). "Purification and some properties of carboxynorspermidine synthase participating in a novel biosynthetic pathway for norspermidine in Vibrio alginolyticus." J Gen Microbiol 137(7);1737-42. PMID: 1955861

Ogishima87: Ogishima T, Deguchi S, Okuda K (1987). "Purification and characterization of cholesterol 7 alpha-hydroxylase from rat liver microsomes." J Biol Chem 262(16);7646-50. PMID: 3584134

Pompeo98: Pompeo F, van Heijenoort J, Mengin-Lecreulx D (1998). "Probing the role of cysteine residues in glucosamine-1-phosphate acetyltransferase activity of the bifunctional GlmU protein from Escherichia coli: site-directed mutagenesis and characterization of the mutant enzymes." J Bacteriol 1998;180(18);4799-803. PMID: 9733680

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Shimotohno88: Shimotohno KW, Seto H, Otake N, Imai S, Murakami T (1988). "Studies on the biosynthesis of bialaphos (SF-1293). 8. Purification and characterization of 2-phosphinomethylmalic acid synthase from Streptomyces hygroscopicus SF-1293." J Antibiot (Tokyo) 41(8);1057-65. PMID: 3170341

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Textor04: Textor S, Bartram S, Kroymann J, Falk KL, Hick A, Pickett JA, Gershenzon J (2004). "Biosynthesis of methionine-derived glucosinolates in Arabidopsis thaliana: recombinant expression and characterization of methylthioalkylmalate synthase, the condensing enzyme of the chain-elongation cycle." Planta 218(6);1026-35. PMID: 14740211

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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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