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MetaCyc Compound: 5,5'-dithio-bis-2-nitrobenzoate

Synonyms: dithionitrobenzoic acid, dithionitrobenzoate, DTNB, 5-(3-carboxy-4-nitro-phenyl)disulfanyl-2-nitro-benzoic acid, 5'-dithio-bis(2-nitrobenzoic acid), 5,5'-dithio-bis(2-nitrobenzoic acid)

Superclasses: a nitrohydrocarbona C-nitro compound

Chemical Formula: C14H6N2O8S2

Molecular Weight: 394.33 Daltons

Monoisotopic Molecular Weight: 397.9878566882 Daltons

5,5'-dithio-bis-2-nitrobenzoate compound structure

SMILES: C1(C=C(C(=CC=1SSC2(=CC=C(C(=C2)C(=O)[O-])[N+]([O-])=O))C(=O)[O-])[N+]([O-])=O)

InChI: InChI=1S/C14H8N2O8S2/c17-13(18)9-5-7(1-3-11(9)15(21)22)25-26-8-2-4-12(16(23)24)10(6-8)14(19)20/h1-6H,(H,17,18)(H,19,20)/p-2


Unification Links: ChemSpider:5367523, PubChem:7000011

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -163.15152Inferred by computational analysis [Latendresse13]

Enzymes inhibited by 5,5'-dithio-bis-2-nitrobenzoate, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: glucosamine-1-phosphate acetyltransferase [Pompeo98, Comment 1], glycerol-3-phosphate dehydrogenase, anaerobic [Schryvers81], prephenate dehydratase [Gething77], aspartate semialdehyde dehydrogenase [Alvarez04], aspartate ammonia-lyase [Helmward89, Suzuki73], threonine dehydrogenase [Boylan81], 3-(2,3-dihydroxyphenyl)propionate 1,2-dioxygenase [Spence96], 4-aminobutyrate transaminase [Schulz90], glyoxalase [Misra95, Comment 2], tRNA-guanine transglycosylase [Garcia97], 6-phosphogluconate dehydrogenase, cyclopropane fatty acyl phospholipid synthase [Taylor79, Grogan97], isocitrate lyase, NADPH-dependent curcumin reductase [Hassaninasab11], glutathione synthetase [Kato88], xanthosine-5'-phosphate:L-glutamine amido-ligase (AMP-forming) [Patel77], 5,10-methylenetetrahydrofolate:glycine hydroxymethyltransferase [JoshiTope90, Schirch85], NAD+-dependent malate dehydrogenase [Kiick84], phosphoenolpyruvate carboxykinase (ITP) [Rios02], D-octopine synthase [Sheikh93], D-arabinose dehydrogenase [Kim98c], myricetin 3-O-glucosyltransferase [Owens], quercetin 3-O-glucosyltransferase [Owens], kaempferol 3-O-glucosyltransferase [Owens], 2-hydroxy-1,4-benzoquinone reductase [Takenaka11], 2-amino-5-carboxymuconic 6-semialdehyde deaminase [Orii04], S-formylglutathione hydrolase [Uotila74], phenylacetyl-coenzyme A:glycine N-acyltransferase [Nandi79], cytidine 5'-monophosphate N-acetylneuraminate synthetase [RodriguezAparic92], N-acetylneuraminate 9-phosphate synthase [Chen02a], nitroalkane oxidase [Kido78], 3-keto-5-aminohexanoate cleavage enzyme [Yorifuji77], dihydropteridine reductase [Firgaira81], glutamine:fructose-6-phosphate amidotransferase [Huynh00], 6-hydroxynicotinate 3-monooxygenase [Nakano99], acetyl-CoA acetyltransferase [Wiesenborn88], guanidinoacetate methyltransferase [Fujioka88], monodehydroascorbate reductase [Murthy94], NAD-dependent formate dehydrogenase [Asano88], acetyl-CoA:13-[O(2')-β-D-glucopyranosyl-β-D-glucopyranosyloxy]docosanoate acetyltransferase [Bucholtz76], deacetoxycephalosporin C synthase [Dotzlaf87], deacetoxycephalosporin C hydroxylase [Dotzlaf87], deacetoxycephalosporin C synthase [Dotzlaf89], deacetoxycephalosporin C hydroxylase [Baker91], dimethylmaleate hydratase [KollmannKoch84], nitrilotriacetate monooxygenase [Uetz92], (25R)-3α,7α,12α-trihydroxy-5β-cholestanoyl-CoA racemase [Schmitz94], choloyl-CoA glycine N-acyltransferase [Killenberg78], 2-hydroxy-4-carboxymuconate-6-semialdehyde dehydrogenase [Masai00], 2-pyrone-4,6-dicarboxylate hydrolase [Masai99] Inhibitor (Other types) of: 1,5-anhydro-D-glucitol dehydrogenase [Yoshida03], mycophenolic acid acyl-glucuronide esterase [Iwamura12], 2-oxoglutarate oxygenase/decarboxylase (ethylene-forming) [Nagahama91], L-allo-threonine aldolase [Kataoka97]


Alvarez04: Alvarez E, Ramon F, Magan C, Diez E (2004). "L-cystine inhibits aspartate-beta-semialdehyde dehydrogenase by covalently binding to the essential 135Cys of the enzyme." Biochim Biophys Acta 1696(1);23-9. PMID: 14726201

Asano88: Asano Y, Sekigawa T, Inukai H, Nakazawa A (1988). "Purification and properties of formate dehydrogenase from Moraxella sp. strain C-1." J Bacteriol 170(7);3189-93. PMID: 3384805

Baker91: Baker BJ, Dotzlaf JE, Yeh WK (1991). "Deacetoxycephalosporin C hydroxylase of Streptomyces clavuligerus. Purification, characterization, bifunctionality, and evolutionary implication." J Biol Chem 266(8);5087-93. PMID: 2002049

Boylan81: Boylan SA, Dekker EE (1981). "L-threonine dehydrogenase. Purification and properties of the homogeneous enzyme from Escherichia coli K-12." J Biol Chem 1981;256(4);1809-15. PMID: 6780553

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

Chen02a: Chen H, Blume A, Zimmermann-Kordmann M, Reutter W, Hinderlich S (2002). "Purification and characterization of N-acetylneuraminic acid-9-phosphate synthase from rat liver." Glycobiology 12(2);65-71. PMID: 11886839

Dotzlaf87: Dotzlaf JE, Yeh WK (1987). "Copurification and characterization of deacetoxycephalosporin C synthetase/hydroxylase from Cephalosporium acremonium." J Bacteriol 169(4);1611-8. PMID: 3558321

Dotzlaf89: Dotzlaf JE, Yeh WK (1989). "Purification and properties of deacetoxycephalosporin C synthase from recombinant Escherichia coli and its comparison with the native enzyme purified from Streptomyces clavuligerus." J Biol Chem 264(17);10219-27. PMID: 2656705

Firgaira81: Firgaira FA, Cotton RG, Danks DM (1981). "Isolation and characterization of dihydropteridine reductase from human liver." Biochem J 197(1);31-43. PMID: 7317032

Fujioka88: Fujioka M, Konishi K, Takata Y (1988). "Recombinant rat liver guanidinoacetate methyltransferase: reactivity and function of sulfhydryl groups." Biochemistry 27(20);7658-64. PMID: 3207695

Garcia97: Garcia GA, Chong S (1997). "Cysteine 265 is in the active site of, but is not essential for catalysis by tRNA-guanine transglycosylase (TGT) from Escherichia coli." J Protein Chem 16(1);11-7. PMID: 9055203

Gething77: Gething MJ, Davidson BE (1977). "Chorismate mutase/prephenate dehydratase from Escherichia coli K12. Modification with 5,5'-dithio-bis(2-nitrobenzoic acid)." Eur J Biochem 1977;78(1);103-10. PMID: 334529

Grogan97: Grogan DW, Cronan JE (1997). "Cyclopropane ring formation in membrane lipids of bacteria." Microbiol Mol Biol Rev 1997;61(4);429-41. PMID: 9409147

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

Helmward89: Helmward Z "Handbook of Enzyme Inhibitors. 2nd, revised and enlarged edition." Weinheim, Federal Republic of Germany ; New York, NY, USA , 1989.

Huynh00: Huynh QK, Gulve EA, Dian T (2000). "Purification and characterization of glutamine:fructose 6-phosphate amidotransferase from rat liver." Arch Biochem Biophys 379(2);307-13. PMID: 10898949

Iwamura12: Iwamura A, Fukami T, Higuchi R, Nakajima M, Yokoi T (2012). "Human α/β hydrolase domain containing 10 (ABHD10) is responsible enzyme for deglucuronidation of mycophenolic acid acyl-glucuronide in liver." J Biol Chem 287(12);9240-9. PMID: 22294686

JoshiTope90: Joshi-Tope G, Schirch V (1990). "The role of a critical sulfhydryl group in the mechanism of serine hydroxymethyltransferase." Ann N Y Acad Sci 585;339-45. PMID: 2113366

Kataoka97: Kataoka M, Wada M, Nishi K, Yamada H, Shimizu S (1997). "Purification and characterization of L-allo-threonine aldolase from Aeromonas jandaei DK-39." FEMS Microbiol Lett 151(2);245-8. PMID: 9228760

Kato88: 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

Kido78: Kido T, Hashizume K, Soda K (1978). "Purification and properties of nitroalkane oxidase from Fusarium oxysporum." J Bacteriol 133(1);53-8. PMID: 22538

Kiick84: Kiick DM, Allen BL, Rao JG, Harris BG, Cook PF (1984). "Determination of dissociation constants for enzyme-reactant complexes for NAD-malic enzyme by modulation of the thiol inactivation rate." Biochemistry 23(23);5454-9. PMID: 6509029

Killenberg78: Killenberg PG, Jordan JT (1978). "Purification and characterization of bile acid-CoA:amino acid N-acyltransferase from rat liver." J Biol Chem 253(4);1005-10. PMID: 624713

Kim98c: Kim ST, Huh WK, Lee BH, Kang SO (1998). "D-arabinose dehydrogenase and its gene from Saccharomyces cerevisiae." Biochim Biophys Acta 1429(1);29-39. PMID: 9920381

KollmannKoch84: Kollmann-Koch A, Eggerer H (1984). "Nicotinic acid metabolism. Dimethylmaleate hydratase." Hoppe Seylers Z Physiol Chem 365(8);847-57. PMID: 6489933

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

Masai00: Masai E, Momose K, Hara H, Nishikawa S, Katayama Y, Fukuda M (2000). "Genetic and biochemical characterization of 4-carboxy-2-hydroxymuconate-6-semialdehyde dehydrogenase and its role in the protocatechuate 4,5-cleavage pathway in Sphingomonas paucimobilis SYK-6." J Bacteriol 182(23);6651-8. PMID: 11073908

Masai99: Masai E, Shinohara S, Hara H, Nishikawa S, Katayama Y, Fukuda M (1999). "Genetic and biochemical characterization of a 2-pyrone-4, 6-dicarboxylic acid hydrolase involved in the protocatechuate 4, 5-cleavage pathway of Sphingomonas paucimobilis SYK-6." J Bacteriol 181(1);55-62. PMID: 9864312

Misra95: Misra K, Banerjee AB, Ray S, Ray M (1995). "Glyoxalase III from Escherichia coli: a single novel enzyme for the conversion of methylglyoxal into D-lactate without reduced glutathione." Biochem J 1995;305 ( Pt 3);999-1003. PMID: 7848303

Murthy94: Murthy SS, Zilinskas BA (1994). "Molecular cloning and characterization of a cDNA encoding pea monodehydroascorbate reductase." J Biol Chem 269(49);31129-33. PMID: 7983054

Nagahama91: Nagahama, K., Ogawa, T., Fujii, T., Tazaki, M., Tanase, S., Morino, Y., Fukuda, H. (1991). "Purification and properties of an ethylene-forming enzyme from Pseudomonas syringae pv. Phaseolicola PK2." Journal of General Microbiology 137(10):2281-2286. PMID: 1770346

Nakano99: Nakano H, Wieser M, Hurh B, Kawai T, Yoshida T, Yamane T, Nagasawa T (1999). "Purification, characterization and gene cloning of 6-hydroxynicotinate 3-monooxygenase from Pseudomonas fluorescens TN5." Eur J Biochem 260(1);120-6. PMID: 10091591

Nandi79: Nandi DL, Lucas SV, Webster LT (1979). "Benzoyl-coenzyme A:glycine N-acyltransferase and phenylacetyl-coenzyme A:glycine N-acyltransferase from bovine liver mitochondria. Purification and characterization." J Biol Chem 254(15);7230-7. PMID: 457678

Orii04: Orii C, Takenaka S, Murakami S, Aoki K (2004). "A novel coupled enzyme assay reveals an enzyme responsible for the deamination of a chemically unstable intermediate in the metabolic pathway of 4-amino-3-hydroxybenzoic acid in Bordetella sp. strain 10d." Eur J Biochem 271(15);3248-54. PMID: 15265044

Owens: Owens DK, McIntosh CA "Identification, recombinant expression, and biochemical characterization of a flavonol 3-O-glucosyltransferase clone from Citrus paradisi." Phytochemistry 70(11-12);1382-91. PMID: 19733370

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

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

Rios02: Rios SE, Nowak T (2002). "Role of cysteine 306 in the catalytic mechanism of Ascaris suum phosphoenolpyruvate carboxykinase." Arch Biochem Biophys 404(1);25-37. PMID: 12127066

RodriguezAparic92: Rodriguez-Aparicio LB, Luengo JM, Gonzalez-Clemente C, Reglero A (1992). "Purification and characterization of the nuclear cytidine 5'-monophosphate N-acetylneuraminic acid synthetase from rat liver." J Biol Chem 267(13);9257-63. PMID: 1577759

Schirch85: Schirch V, Hopkins S, Villar E, Angelaccio S (1985). "Serine hydroxymethyltransferase from Escherichia coli: purification and properties." J Bacteriol 1985;163(1);1-7. PMID: 3891721

Schmitz94: Schmitz W, Fingerhut R, Conzelmann E (1994). "Purification and properties of an alpha-methylacyl-CoA racemase from rat liver." Eur J Biochem 222(2);313-23. PMID: 8020470

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

Schulz90: Schulz A, Taggeselle P, Tripier D, Bartsch K (1990). "Stereospecific production of the herbicide phosphinothricin (glufosinate) by transamination: isolation and characterization of a phosphinothricin-specific transaminase from Escherichia coli." Appl Environ Microbiol 1990;56(1);1-6. PMID: 2178550

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

Spence96: Spence EL, Kawamukai M, Sanvoisin J, Braven H, Bugg TD (1996). "Catechol dioxygenases from Escherichia coli (MhpB) and Alcaligenes eutrophus (MpcI): sequence analysis and biochemical properties of a third family of extradiol dioxygenases." J Bacteriol 1996;178(17);5249-56. PMID: 8752345

Suzuki73: Suzuki S, Yamaguchi J, Tokushige M (1973). "Studies on aspartase. I. Purification and molecular properties of aspartase from Escherichia coli." Biochim Biophys Acta 1973;321(1);369-81. PMID: 4584395

Takenaka11: Takenaka S, Koshiya J, Okugawa S, Takata A, Murakami S, Aoki K (2011). "Fe-superoxide dismutase and 2-hydroxy-1,4-benzoquinone reductase preclude the auto-oxidation step in 4-aminophenol metabolism by Burkholderia sp. strain AK-5." Biodegradation 22(1);1-11. PMID: 20480210

Taylor79: Taylor FR, Cronan JE (1979). "Cyclopropane fatty acid synthase of Escherichia coli. Stabilization, purification, and interaction with phospholipid vesicles." Biochemistry 1979;18(15);3292-300. PMID: 380648

Uetz92: Uetz T, Schneider R, Snozzi M, Egli T (1992). "Purification and characterization of a two-component monooxygenase that hydroxylates nitrilotriacetate from "Chelatobacter" strain ATCC 29600." J Bacteriol 174(4);1179-88. PMID: 1735711

Uotila74: Uotila L, Koivusalo M (1974). "Purification and properties of S-formylglutathione hydrolase from human liver." J Biol Chem 249(23);7664-72. PMID: 4436331

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

Yorifuji77: Yorifuji T, Jeng IM, Barker HA (1977). "Purification and properties of 3-keto-5-aminohexanoate cleavage enzyme from a lysine-fermenting Clostridium." J Biol Chem 252(1);20-31. PMID: 13064

Yoshida03: Yoshida N, Uchida E, Katsuragi T, Tani Y (2003). "A novel NAD-dependent dehydrogenase, highly specific for 1,5-anhydro-D-glucitol, from Trichoderma longibrachiatum strain 11-3." Appl Environ Microbiol 69(5);2603-7. PMID: 12732527

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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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