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MetaCyc Compound: p-chloromercuriphenylsulfonate

Synonyms: p-chloromercuriphenyl sulphonate, p-chloromercuriphenyl sulphonic acid, p-CMPSA, p-chloromercuriphenylsulphonate, PCMBS, 4-chloromercuribenzenesulfonate, p-chloromercuribenzenesulfonate

Chemical Formula: C6H4O3SClHg

Molecular Weight: 392.2 Daltons

Monoisotopic Molecular Weight: 393.93541842679997 Daltons

SMILES: C1(C=CC(=CC=1)S(=O)([O-])=O)[Hg]Cl

InChI: InChI=1S/C6H5O3S.ClH.Hg/c7-10(8,9)6-4-2-1-3-5-6;;/h2-5H,(H,7,8,9);1H;/q;;+1/p-2

InChIKey: InChIKey=XXEBDPRHFAWOND-UHFFFAOYSA-L

Unification Links: ChEBI:33207 , ChemSpider:4574181 , PubChem:5460705

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -24.007578 Inferred by computational analysis [Latendresse13]

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

Inhibitor (Uncompetitive) of: diamine oxidase [Suzuki96]

Inhibitor (Mechanism unknown) of: 13-hydroxylupanine O-tigloyltransferase [Suzuki94a] , GDP-mannose 4,6-dehydratase [ELBEIN65] , glycerol-3-phosphate dehydrogenase, anaerobic [Schryvers81] , D-glucarate dehydratase [Blumenthal66] , sulfite reductase [Siegel74] , glycerol-3-phosphate:phosphate antiporter [Fann03] , gentisyl alcohol epoxidase [Priest89] , D-octopine synthase [Sheikh93] , vicianin hydrolase [Lizotte88] , emodin O-methyltransferase [Chen92b] , phosphatidyl-N-methylethanolamine N-methyltransferase [Gaynor90] , phosphatidylethanolamine N-methyltransferase [Gaynor90] , 5-dehydro-4-deoxy-D-glucarate dehydratase [Dagley75] , carnitine O-acetyltransferase [Miyazawa83a] , L-gulonate 3-dehydrogenase [Ishikura05] , β-ureidopropionase [Walsh01] , acetoacetate decarboxylase [Boyer72, Autor70] , (S)-6-hydroxynicotine oxidase [Dai68] , 2,7,4-trihydroxyisoflavanone hydro-lyase (daidzein-forming) [Hakamatsuka98] , UDP-D-xylose 4-epimerase [Fan70] , betanidin 5-O-glucosyltransferase [Vogt97] , betanidin 6-O-glucosyltransferase [Vogt97]

Inhibitor (Other types) of: oxalyl-CoA decarboxylase [Quayle63a]


References

Autor70: Autor AP, Fridovich I (1970). "The interactions of acetoacetate decarboxylase with carbonyl compounds, hydrogen cyanide, and an organic mercurial." J Biol Chem 1970;245(20);5214-22. PMID: 5469163

Blumenthal66: Blumenthal H "D-Glucarate Dehydrase." Meth Enz 1966;9:660-665.

Boyer72: Boyer PD, editor (1972). "Chapter 8- Acetoacetate Decarboxylase." The Enzymes, Third Edition, Volume Six, Carboxylation and decarboxylation (nonoxidative) isomerization, Academic Press New York.

Chen92b: Chen ZG, Fujii I, Ebizuka Y, Sankawa U (1992). "Emodin O-methyltransferase from Aspergillus terreus." Arch Microbiol 158(1);29-34. PMID: 1444712

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

Dai68: Dai VD, Decker K, Sund H (1968). "Purification and properties of L-6-hydroxynicotine oxidase." Eur J Biochem 1968;4(1);95-102. PMID: 5646150

ELBEIN65: ELBEIN AD, HEATH EC (1965). "THE BIOSYNTHESIS OF CELL WALL LIPOPOLYSACCHARIDE IN ESCHERICHIA COLI. II. GUANOSINE DIPHOSPHATE 4-KETO-6-DEOXY-D-MANNOSE, AN INTERMEDIATE IN THE BIOSYNTHESIS OF GUANOSINE DIPHOSPHATE COLITOSE." J Biol Chem 240;1926-31. PMID: 14299611

Fan70: Fan DF, Feingold DS (1970). "Nucleoside diphosphate-sugar 4-epimerases. II. Uridine diphosphate arabinose 4-epimerase of wheat germ." Plant Physiol 46(4);592-5. PMID: 5483919

Fann03: Fann MC, Busch A, Maloney PC (2003). "Functional characterization of cysteine residues in GlpT, the glycerol 3-phosphate transporter of Escherichia coli." J Bacteriol 185(13);3863-70. PMID: 12813080

Gaynor90: Gaynor PM, Carman GM (1990). "Phosphatidylethanolamine methyltransferase and phospholipid methyltransferase activities from Saccharomyces cerevisiae. Enzymological and kinetic properties." Biochim Biophys Acta 1045(2);156-63. PMID: 2198947

Hakamatsuka98: Hakamatsuka T, Mori K, Ishida S, Ebizuka Y, Sankawa U, (1998) "Purification of 2-hydroxyisoflavanone dehydratase from the cell cultures of Pueraria lobata." Phytochemistry (1998), 49(2), 497-505.

Ishikura05: Ishikura S, Usami N, Araki M, Hara A (2005). "Structural and functional characterization of rabbit and human L-gulonate 3-dehydrogenase." J Biochem (Tokyo) 137(3);303-14. PMID: 15809331

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

Lizotte88: Lizotte PA, Poulton JE (1988). "Catabolism of Cyanogenic Glycosides by Purified Vicianin Hydrolase from Squirrel's Foot Fern (Davallia Trichomanoides Blume)." Plant Physiol 86(2);322-4. PMID: 16665903

Miyazawa83a: Miyazawa S, Ozasa H, Furuta S, Osumi T, Hashimoto T (1983). "Purification and properties of carnitine acetyltransferase from rat liver." J Biochem 93(2);439-51. PMID: 6404901

Priest89: Priest JW, Light RJ (1989). "Patulin biosynthesis: epoxidation of toluquinol and gentisyl alcohol by particulate preparations from Penicillium patulum." Biochemistry 28(23);9192-200. PMID: 2605253

Quayle63a: Quayle JR (1963). "Carbon assimilation by Pseudomonas oxalaticus OX1. 7. decarboxylation of oxalyl-coenzyme A to formyl-coenzyme A." Biochem J 89;492-503. PMID: 14101969

Schryvers81: Schryvers A, Weiner JH (1981). "The anaerobic sn-glycerol-3-phosphate dehydrogenase of Escherichia coli. Purification and characterization." J Biol Chem 1981;256(19);9959-65. PMID: 6792201

Sheikh93: Sheikh S, Katiyar SS (1993). "Chemical modification of octopine dehydrogenase by thiol-specific reagents: evidence for the presence of an essential cysteine at the catalytic site." Biochim Biophys Acta 1202(2);251-7. PMID: 8399387

Siegel74: Siegel LM, Davis PS, Kamin H (1974). "Reduced nicotinamide adenine dinucleotide phosphate-sulfite reductase of enterobacteria. 3. The Escherichia coli hemoflavoprotein: catalytic parameters and the sequence of electron flow." J Biol Chem 1974;249(5);1572-86. PMID: 4150390

Suzuki94a: Suzuki H, Murakoshi I, Saito K (1994). "A novel O-tigloyltransferase for alkaloid biosynthesis in plants. Purification, characterization, and distribution in Lupinus plants." J Biol Chem 269(22);15853-60. PMID: 8195240

Suzuki96: Suzuki Y. "Purification and characterization of diamine oxidase from Triticum aesticum shoots." Phytochemistry (1996) 42(2) : 291-293.

Vogt97: Vogt T, Zimmermann E, Grimm R, Meyer M, Strack D (1997). "Are the characteristics of betanidin glucosyltransferases from cell-suspension cultures of Dorotheanthus bellidiformis indicative of their phylogenetic relationship with flavonoid glucosyltransferases?." Planta 203(3);349-61. PMID: 9431682

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


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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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