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Escherichia coli K-12 substr. MG1655 Compound: p-chloromercuribenzoate

Synonyms: 4-chloromercuribenzoic acid, (4-carboxyphenyl)-chloro-mercury, p-CMB

Chemical Formula: C7H4O2ClHg

Molecular Weight: 356.15 Daltons

Monoisotopic Molecular Weight: 357.9684331147 Daltons

SMILES: C1(=CC=C(C=C1)C(=O)[O-])[Hg]Cl

InChI: InChI=1S/C7H5O2.ClH.Hg/c8-7(9)6-4-2-1-3-5-6;;/h2-5H,(H,8,9);1H;/q;;+1/p-2

InChIKey: InChIKey=YFZOUMNUDGGHIW-UHFFFAOYSA-L

Unification Links: ChEBI:10620 , ChemSpider:10606363 , KEGG:C03444 , PubChem:21226146

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -51.03

Enzymes inhibited by p-chloromercuribenzoate, sorted by the type of inhibition, are:

Inhibitor (Noncompetitive) of: D-mannonate oxidoreductase [Hickman60, Portalier72a]

Inhibitor (Mechanism unknown) of: N-acetyl-β-neuraminate lyase [Aisaka91, Uchida84] , 3-chloro-D-alanine dehydrochlorinase [Nagasawa85] , NADPH-dependent curcumin reductase [Hassaninasab11] , acetate kinase [Rose54] , penicillinase [Tamura76] , D-alanyl-D-alanine carboxypeptidase [Tamura76] , D-mannonate dehydratase [RobertBaudouy73] , 2,3-dihydroxy-3-methylvalerate hydro-lyase [Myers61] , 2,3-dihydroxy-isovalerate dehydratase [Myers61] , pyrroline-5-carboxylate reductase [Rossi77a] , acetoacetyl-CoA transferase [Sramek75] , glycogen phosphorylase-limit dextrin α-1,6-glucohydrolase [Jeanningros76] , L-rhamnose isomerase [Takagi64, Comment 1] , glycogen phosphorylase [Chen68, Chen68a] , xanthosine-5'-phosphate:L-glutamine amido-ligase (AMP-forming) [Patel77] , trimethylamine N-oxide reductase [Shimokawa79, Silvestro88] , glutathione synthetase [Kato88a] , methylglyoxal reductase (NADPH-dependent) [Saikusa87] , nitrite reductase [Coleman78] , glutamate-5-semialdehyde dehydrogenase [Hayzer82] , D-glucuronate isomerase [Ashwell60] , D-galacturonate isomerase [Ashwell60, Takagi59] , betaine aldehyde dehydrogenase [Falkenberg90] , N-acetylneuraminate lyase [Aisaka91, Uchida84] , altronate oxidoreductase [Hickman60, Portalier82, Comment 2] , 6-phosphogluconate dehydrogenase , adenosine deaminase [Nygaard78] , phosphoglucomutase [Joshi64a] , amylomaltase [Wiesmeyer60] , 2,4-dienoyl-CoA reductase [Dommes84] , D-arabinose 5-phosphate isomerase [Lim66] , malonyl-CoA-ACP transacylase [Ruch73] , glycolate oxidase [Lord72] , thiamin monophosphate kinase [Nishino72]


References

Aisaka91: Aisaka K, Igarashi A, Yamaguchi K, Uwajima T (1991). "Purification, crystallization and characterization of N-acetylneuraminate lyase from Escherichia coli." Biochem J 1991;276 ( Pt 2);541-6. PMID: 1646603

Ashwell60: Ashwell G, Wahba AJ, Hickman J (1960). "Uronic acid metabolism in bacteria. I. Purification and properties of uronic acid isomerase in Escherichia coli." J Biol Chem 1960;235(6):1559-1565. PMID: 13794771

Chen68: Chen GS, Segel IH (1968). "Escherichia coli polyglucose phosphorylases." Arch Biochem Biophys 1968;127(1);164-74. PMID: 4878694

Chen68a: Chen GS, Segel IH (1968). "Purification and properties of glycogen phosphorylase from Escherichia coli." Arch Biochem Biophys 1968;127(1);175-86. PMID: 4878695

Coleman78: Coleman KJ, Cornish-Bowden A, Cole JA (1978). "Purification and properties of nitrite reductase from Escherichia coli K12." Biochem J 1978;175(2);483-93. PMID: 217342

Dommes84: Dommes V, Kunau WH (1984). "2,4-Dienoyl coenzyme A reductases from bovine liver and Escherichia coli. Comparison of properties." J Biol Chem 1984;259(3);1781-8. PMID: 6363415

Falkenberg90: Falkenberg P, Strom AR (1990). "Purification and characterization of osmoregulatory betaine aldehyde dehydrogenase of Escherichia coli." Biochim Biophys Acta 1990;1034(3);253-9. PMID: 2194570

Hassaninasab11: Hassaninasab A, Hashimoto Y, Tomita-Yokotani K, Kobayashi M (2011). "Discovery of the curcumin metabolic pathway involving a unique enzyme in an intestinal microorganism." Proc Natl Acad Sci U S A 108(16):6615-20. PMID: 21467222

Hayzer82: Hayzer DJ, Leisinger T (1982). "Proline biosynthesis in Escherichia coli. Purification and characterisation of glutamate-semialdehyde dehydrogenase." Eur J Biochem 1982;121(3);561-5. PMID: 7035170

Hickman60: Hickman J, Ashwell G (1960). "Uronic acid metabolism in bacteria. II. Purification and properties of D-altronic acid and D-mannonic acid dehydrogenases in Escherichia coli." J Biol Chem 235;1566-70. PMID: 14401695

Jeanningros76: Jeanningros R, Creuzet-Sigal N, Frixon C, Cattaneo J (1976). "Purification and properties of a debranching enzyme from Escherichia coli." Biochim Biophys Acta 1976;438(1);186-99. PMID: 779849

Joshi64a: Joshi JG, Handler P (1964). "Phosphoglucomutase. I. Purification and properties of phosphoglucomutase from Escherichia coli." J. Biol. Chem. 239:2741-2751. PMID: 14216423

Kato88a: Kato H, Tanaka T, Nishioka T, Kimura A, Oda J (1988). "Role of cysteine residues in glutathione synthetase from Escherichia coli B. Chemical modification and oligonucleotide site-directed mutagenesis." J Biol Chem 1988;263(24);11646-51. PMID: 3042775

Lim66: Lim R, Cohen SS (1966). "D-phosphoarabinoisomerase and D-ribulokinase in Escherichia coli." J Biol Chem 1966;241(19);4304-15. PMID: 5332197

Lord72: Lord JM (1972). "Glycolate oxidoreductase in Escherichia coli." Biochim Biophys Acta 1972;267(2);227-37. PMID: 4557653

Myers61: Myers JW (1961). "Dihydroxy acid dehydrase: an enzyme involved in the biosynthesis of isoleucine and valine." J Biol Chem 236;1414-8. PMID: 13727223

Nagasawa85: Nagasawa T, Ishii T, Kumagai H, Yamada H (1985). "D-Cysteine desulfhydrase of Escherichia coli. Purification and characterization." Eur J Biochem 1985;153(3);541-51. PMID: 3908101

Nishino72: Nishino H (1972). "Biogenesis of cocarboxylase in Escherichia coli. Partial purification and some properties of thiamine monophosphate kinase." J Biochem (Tokyo) 1972;72(5);1093-100. PMID: 4567662

Nygaard78: Nygaard P (1978). "Adenosine deaminase from Escherichia coli." Methods Enzymol 1978;51;508-12. PMID: 357905

Patel77: Patel N, Moyed HS, Kane JF (1977). "Properties of xanthosine 5'-monophosphate-amidotransferase from Escherichia coli." Arch Biochem Biophys 1977;178(2);652-61. PMID: 189701

Portalier72a: Portalier RC, Stoeber FR (1972). "[D-mannonate: NAD oxidoreductase from Escherichia coli K12. Purification, properties and specificity]." Eur J Biochem 1972;26(2);290-300. PMID: 4402996

Portalier72b: Portalier RC, Stoeber FR (1972). "[D-altronate: NAD-oxidoreductase in Escherichia coli K12. Purification, properties, and specificity]." Eur J Biochem 1972;26(1);50-61. PMID: 4402917

Portalier82: Portalier R, Stoeber F (1982). "D-Mannonate and D-altronate-NAD dehydrogenases from Escherichia coli." Methods Enzymol 89 Pt D;210-8. PMID: 6755169

RobertBaudouy73: Robert-Baudouy JM, Stoeber FR (1973). "[Purification and properties of D-mannonate hydrolyase from Escherichia coli K12]." Biochim Biophys Acta 1973;309(2);473-85. PMID: 4581499

Rose54: Rose IA, Grunberg-Manago M, Korey SR, Ochoa S (1954). "Enzymatic phosphorylation of acetate." J Biol Chem 211(2);737-56. PMID: 13221579

Rossi77a: Rossi JJ, Vender J, Berg CM, Coleman WH (1977). "Partial purification and some properties of delta1-pyrroline-5-carboxylate reductase from Escherichia coli." J Bacteriol 1977;129(1);108-14. PMID: 12133

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

Saikusa87: Saikusa T, Rhee H, Watanabe K, Murata K, Kimura A (1987). "Metabolism of 2-oxoaldehydes in bacteria: purification and characterization of methylglyoxal reductase from E. coli." Agricultural and Biological Chemistry 51(7): 1893-1899.

Shimokawa79: Shimokawa O, Ishimoto M (1979). "Purification and some properties of inducible tertiary amine N-oxide reductase from Escherichia coli." J Biochem (Tokyo) 1979;86(6);1709-17. PMID: 393699

Silvestro88: Silvestro A, Pommier J, Giordano G (1988). "The inducible trimethylamine-N-oxide reductase of Escherichia coli K12: biochemical and immunological studies." Biochim Biophys Acta 1988;954(1);1-13. PMID: 3282544

Sramek75: Sramek SJ, Frerman FE (1975). "Purification and properties of Escherichia coli coenzyme A-transferase." Arch Biochem Biophys 1975;171(1);14-26. PMID: 1103739

Takagi59: Takagi Y, Kanda M, Nakata Y (1959). "Studies on a D-galacturonic acid isomerase." Biochim Biophys Acta 31(1);264-5. PMID: 13628636

Takagi64: Takagi Y, Sawada H (1964). "The metabolism of L-rhamnose in Escherichia coli. I. L-rhamnose isomerase." Biochim Biophys Acta 92:10-17. PMID: 14243758

Tamura76: Tamura T, Imae Y, Strominger JL (1976). "Purification to homogeneity and properties of two D-alanine carboxypeptidases I From Escherichia coli." J Biol Chem 251(2);414-23. PMID: 1391

Uchida84: Uchida Y, Tsukada Y, Sugimori T (1984). "Purification and properties of N-acetylneuraminate lyase from Escherichia coli." J Biochem 96(2);507-22. PMID: 6389524

Wiesmeyer60: Wiesmeyer H, Cohn M (1960). "The characterization of the pathway of maltose utilization by Escherichia coli: II. General properties and mechanism of action of amylomaltase." Biochim Biophys Acta 39:427-439. PMID: 13844669


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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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