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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 compoundan organoiodine compound

Chemical Formula: C2H4NOI

Molecular Weight: 184.96 Daltons

Monoisotopic Molecular Weight: 184.9337567557 Daltons

iodoacetamide compound structure


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


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

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 2.0444808Inferred 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: glucosamine-1-phosphate acetyltransferase [Pompeo98], formate dehydrogenase N [Enoch75], homoserine O-succinyltransferase [Born99, Comment 1], isopentenyl diphosphate isomerase [Fujisaki86, Comment 2], malonyl-CoA-ACP transacylase [Ruch73], acetyl-CoA:ACP transacylase [Lowe88], amidophosphoribosyl transferase [Messenger79], farnesyl diphosphate synthase [Fujisaki86], geranyl diphosphate synthase [Fujisaki86], β-ketoacyl-ACP synthase [Greenspan69, Comment 3], acetoacetyl-[acp] synthase [Greenspan69, Comment 3], acyl-CoA thioesterase [Naggert91], 3-ketoacyl-CoA thiolase [Yang83], glutathionylspermidine amidase [Lin97], 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 [Liu99a], hydantoin racemase [Wiese00], loganic acid O-methyltransferase [Madyastha73], desoxyhemigossypol-6-O-methyltransferase [Liu99b], 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 [Alber06a], lactaldehyde dehydrogenase [Grochowski06]


Alber06a: Alber B, Olinger M, Rieder A, Kockelkorn D, Jobst B, Hugler M, Fuchs G (2006). "Malonyl-coenzyme A reductase in the modified 3-hydroxypropionate cycle for autotrophic carbon fixation in archaeal Metallosphaera and Sulfolobus spp." J Bacteriol 188(24);8551-9. PMID: 17041055

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

Born99: Born TL, Blanchard JS (1999). "Enzyme-catalyzed acylation of homoserine: mechanistic characterization of the Escherichia coli metA-encoded homoserine transsuccinylase." Biochemistry 1999;38(43);14416-23. PMID: 10572016

Bucholtz76: Bucholtz ML, Light RJ (1976). "Acetylation of 13-sophorosyloxydocosanoic acid by an acetyltransferase purified from Candida bogoriensis." J Biol Chem 251(2);424-30. PMID: 1245481

Cardinale68: Cardinale GJ, Abeles RH (1968). "Purification and mechanism of action of proline racemase." Biochemistry 1968;7(11);3970-8. PMID: 5722267

Child63: Child JJ, Simpson FJ, Westlake DWS (1963). "Degradation of rutin by Aspergillus flavus. Production, purification and characterization of an esterase." Can J Microbiol 9:653-664.

Child98: Child CJ, Shoolingin-Jordan PM (1998). "Inactivation of the polyketide synthase, 6-methylsalicylic acid synthase, by the specific modification of Cys-204 of the beta-ketoacyl synthase by the fungal mycotoxin cerulenin." Biochem J 330 ( Pt 2);933-7. PMID: 9480912

Curir03: Curir P, Lanzotti V, Dolci M, Dolci P, Pasini C, Tollin G (2003). "Purification and properties of a new S-adenosyl-L-methionine:flavonoid 4'-O-methyltransferase from carnation (Dianthus caryophyllus L.)." Eur J Biochem 270(16);3422-31. PMID: 12899699

Dagley75: Dagley S, Jeffcoat R (1975). "D-4-deoxy-5-ketoglucarate hydro-lyase (decarboxylating)." Methods Enzymol 42;272-6. PMID: 237186

Dailey86: Dailey HA (1986). "Purification and characterization of bacterial ferrochelatase." Methods Enzymol 123;408-15. PMID: 3702737

Enoch75: Enoch HG, Lester RL (1975). "The purification and properties of formate dehydrogenase and nitrate reductase from Escherichia coli." J Biol Chem 1975;250(17);6693-705. PMID: 1099093

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

Friedmann07: Friedmann S, Alber BE, Fuchs G (2007). "Properties of R-citramalyl-coenzyme A lyase and its role in the autotrophic 3-hydroxypropionate cycle of Chloroflexus aurantiacus." J Bacteriol 189(7);2906-14. PMID: 17259315

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

Greenspan69: Greenspan MD, Alberts AW, Vagelos PR (1969). "Acyl carrier protein. 13. Beta-ketoacyl acyl carrier protein synthetase from Escherichia coli." J Biol Chem 1969;244(23);6477-85. PMID: 4901371

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

Hartmanis87: Hartmanis MG (1987). "Butyrate kinase from Clostridium acetobutylicum." J Biol Chem 1987;262(2);617-21. PMID: 3027059

Harvima85: Harvima RJ, Kajander EO, Harvima IT, Fraki JE (1985). "Purification and partial characterization of rat kidney histamine-N-methyltransferase." Biochim Biophys Acta 841(1);42-9. PMID: 4016144

Jeng74: Jeng I, Barker HA (1974). "Purification and properties of l-3-aminobutyryl coenzyme A deaminase from a lysine-fermenting Clostridium." J Biol Chem 249(20);6578-84. PMID: 4420467

Jones93: Jones RM, Jordan PM (1993). "Purification and properties of the uroporphyrinogen decarboxylase from Rhodobacter sphaeroides." Biochem J 293 ( Pt 3);703-12. PMID: 8352737

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

Liu99a: 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

Liu99b: 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

Messenger79: Messenger LJ, Zalkin H (1979). "Glutamine phosphoribosylpyrophosphate amidotransferase from Escherichia coli. Purification and properties." J Biol Chem 1979;254(9);3382-92. PMID: 372191

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

Naggert91: Naggert J, Narasimhan ML, DeVeaux L, Cho H, Randhawa ZI, Cronan JE, Green BN, Smith S (1991). "Cloning, sequencing, and characterization of Escherichia coli thioesterase II." J Biol Chem 1991;266(17);11044-50. PMID: 1645722

Nakada03: Nakada Y, Itoh Y (2003). "Identification of the putrescine biosynthetic genes in Pseudomonas aeruginosa and characterization of agmatine deiminase and N-carbamoylputrescine amidohydrolase of the arginine decarboxylase pathway." Microbiology 149(Pt 3);707-14. PMID: 12634339

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

Raha90: Raha SK, Roy SK, Dey SK, Chakrabarty SL (1990). "Purification and properties of an L-asparaginase from Cylindrocarpon obtusisporum MB-10." Biochem Int 21(6);987-1000. PMID: 2080924

Roberts74: Roberts, M.F (1974). "An S-adenosyl-L-methionine; coniine methyltransferase from Conium maculatum." Phytochemistry, 13, 1847-1851.

Ruch73: Ruch FE, Vagelos PR (1973). "The isolation and general properties of Escherichia coli malonyl coenzyme A-acyl carrier protein transacylase." J Biol Chem 1973;248(23);8086-94. PMID: 4584822

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

Steimle97: Steimle PA, Lindmark DG, Jarroll EL (1997). "Purification and characterization of encystment-induced glucosamine 6-phosphate isomerase in Giardia." Mol Biochem Parasitol 84(1);149-53. PMID: 9041531

Tanigawa10: Tanigawa M, Shinohara T, Saito M, Nishimura K, Hasegawa Y, Wakabayashi S, Ishizuka M, Nagata Y (2010). "D-Amino acid dehydrogenase from Helicobacter pylori NCTC 11637." Amino Acids 38(1);247-55. PMID: 19212808

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

Usui89: Usui S, Yu CA (1989). "Purification and properties of isopenicillin N epimerase from Streptomyces clavuligerus." Biochim Biophys Acta 999(1);78-85. PMID: 2804141

Walsh01: Walsh TA, Green SB, Larrinua IM, Schmitzer PR (2001). "Characterization of plant beta-ureidopropionase and functional overexpression in Escherichia coli." Plant Physiol 125(2);1001-11. PMID: 11161056

Wharfe79: Wharfe J, Harwood JL (1979). "Lipid metabolism in germinating seeds. Purification of ethanolamine kinase from soya bean." Biochim Biophys Acta 575(1);102-11. PMID: 228735

Wiese00: Wiese A, Pietzsch M, Syldatk C, Mattes R, Altenbuchner J (2000). "Hydantoin racemase from Arthrobacter aurescens DSM 3747: heterologous expression, purification and characterization." J Biotechnol 80(3);217-30. PMID: 10949312

Wiesenborn88: Wiesenborn DP, Rudolph FB, Papoutsakis ET (1988). "Thiolase from Clostridium acetobutylicum ATCC 824 and Its Role in the Synthesis of Acids and Solvents." Appl Environ Microbiol 54(11);2717-2722. PMID: 16347774

Yang83: Yang SY, Schulz H (1983). "The large subunit of the fatty acid oxidation complex from Escherichia coli is a multifunctional polypeptide. Evidence for the existence of a fatty acid oxidation operon (fad AB) in Escherichia coli." J Biol Chem 1983;258(16);9780-5. PMID: 6350283

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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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