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Chemical Compound Review

AC1MQOOV     4-nitrobenzene-1,2-diol

Synonyms: PubChem22910, CPD-158, CHEMBL42423, SureCN156909, N15553_ALDRICH, ...
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Disease relevance of NSC 80651


High impact information on NSC 80651

  • The number of binding sites per enzyme molecule titrated spectrophotometrically with 4-nitrocatechol agrees with results from previous studies with either the principal substrate or other analogues, as expected of an effective probe [6].
  • The apparent molecular weight of 60,000, the preferential cleavage of 4-nitrocatechol sulfate (PNCS) over p-acetyl-benzenesulfonic acid (PABS), inhibition by phosphate ions and pH optimum of 5.7 are characteristics of a type II B arylsulfatase [7].
  • Here, it is shown that the reaction cycle kinetics can be monitored by utilizing the alternative substrate 4-nitrocatechol (4NC), which is also cleaved in the proximal extradiol position [8].
  • In addition, the structures of Ac 3,4-PCD complexed with its substrate 3, 4-dihydroxybenzoic acid (PCA), the inhibitor 4-nitrocatechol (4-NC), or cyanide (CN(-)) have been solved using native phases [9].
  • Rat liver and human skin fibroblasts arylsulphatase A and B activities on both 4-methylumbelliferyl sulphate and 4-nitrocatechol sulphate were compared [10].

Chemical compound and disease context of NSC 80651


Biological context of NSC 80651

  • Experiments with extracts obtained from PNP-grown cells revealed that the initial reaction is a hydroxylation of PNP to yield 4-nitrocatechol [15].
  • Saturation mutagenesis at this position resulted in the generation of two more nitrocatechol mutants, I100A and I100S; the rate of 4-nitrocatechol formation by I100A was more than 16 times higher than that of wild-type T4MO at 200 microM nitrobenzene (0.13 +/- 0.01 vs. 0.008 +/- 0.001 nmol/ protein) [16].

Anatomical context of NSC 80651


Associations of NSC 80651 with other chemical compounds


Gene context of NSC 80651


Analytical, diagnostic and therapeutic context of NSC 80651

  • A complex between native, iron(II) soybean lipoxygenase 3 and 4-nitrocatechol, a known inhibitor of the enzyme, has been detected by isothermal titration calorimetry and characterized by X-ray crystallography [28].
  • The circular dichroism spectrum of the complex of Fe(III)-lipoxygenase-1 and 4-nitrocatechol has a positive band at around 380 nm and a negative band at around 450 nm and is significantly different from that of the Fe(III)-enzyme as such [29].


  1. Conversion of p-nitrophenol to 4-nitrocatechol by a Pseudomonas sp. Sudhakar-Barik, n.u.l.l., Siddaramappa, R., Wahid, P.A., Sethunathan, N. Antonie Van Leeuwenhoek (1978) [Pubmed]
  2. Plasmid-encoded degradation of p-nitrophenol and 4-nitrocatechol by Arthrobacter protophormiae. Chauhan, A., Chakraborti, A.K., Jain, R.K. Biochem. Biophys. Res. Commun. (2000) [Pubmed]
  3. Characterization of Rhodococcus wratislaviensis strain J3 that degrades 4-nitrocatechol and other nitroaromatic compounds. Navrátilová, J., Tvrzová, L., Durnová, E., Spröer, C., Sedlácek, I., Neca, J., Nemec, M. Antonie Van Leeuwenhoek (2005) [Pubmed]
  4. Degradation of p-nitrophenol by the phototrophic bacterium Rhodobacter capsulatus. Roldán, M.D., Blasco, R., Caballero, F.J., Castillo, F. Arch. Microbiol. (1998) [Pubmed]
  5. Degradation of 4-nitrocatechol by Burkholderia cepacia: a plasmid-encoded novel pathway. Chauhan, A., Samanta, S.K., Jain, R.K. J. Appl. Microbiol. (2000) [Pubmed]
  6. 4-Nitrocatechol as a colorimetric probe for non-heme iron dioxygenases. Tyson, C.A. J. Biol. Chem. (1975) [Pubmed]
  7. Inactivation of slow reacting substance of anaphylaxis by human eosinophil arylsulfatase. Wasserman, S.I., Goetzl, E.J., Austen, K.F. J. Immunol. (1975) [Pubmed]
  8. Single-turnover kinetics of homoprotocatechuate 2,3-dioxygenase. Groce, S.L., Miller-Rodeberg, M.A., Lipscomb, J.D. Biochemistry (2004) [Pubmed]
  9. Structure of Acinetobacter strain ADP1 protocatechuate 3, 4-dioxygenase at 2.2 A resolution: implications for the mechanism of an intradiol dioxygenase. Vetting, M.W., D'Argenio, D.A., Ornston, L.N., Ohlendorf, D.H. Biochemistry (2000) [Pubmed]
  10. Comparative activity of arylsulphatases A and B on two synthetic substrates. Delvin, E.E., Pottier, A., Glorieux, F. Biochem. J. (1976) [Pubmed]
  11. Whole cell-enzyme hybrid amperometric biosensor for direct determination of organophosphorous nerve agents with p-nitrophenyl substituent. Lei, Y., Mulchandani, P., Chen, W., Wang, J., Mulchandani, A. Biotechnol. Bioeng. (2004) [Pubmed]
  12. Protein engineering of toluene-o-xylene monooxygenase from Pseudomonas stutzeri OX1 for oxidizing nitrobenzene to 3-nitrocatechol, 4-nitrocatechol, and nitrohydroquinone. Vardar, G., Ryu, K., Wood, T.K. J. Biotechnol. (2005) [Pubmed]
  13. Biodegradation of methyl parathion and p-nitrophenol: evidence for the presence of a p-nitrophenol 2-hydroxylase in a Gram-negative Serratia sp. strain DS001. Pakala, S.B., Gorla, P., Pinjari, A.B., Krovidi, R.K., Baru, R., Yanamandra, M., Merrick, M., Siddavattam, D. Appl. Microbiol. Biotechnol. (2007) [Pubmed]
  14. Acetaminophen-induced hepatotoxicity of gel entrapped rat hepatocytes in hollow fibers. Shen, C., Zhang, G., Qiu, H., Meng, Q. Chem. Biol. Interact. (2006) [Pubmed]
  15. A two-component monooxygenase catalyzes both the hydroxylation of p-nitrophenol and the oxidative release of nitrite from 4-nitrocatechol in Bacillus sphaericus JS905. Kadiyala, V., Spain, J.C. Appl. Environ. Microbiol. (1998) [Pubmed]
  16. Protein engineering of toluene 4-monooxygenase of Pseudomonas mendocina KR1 for synthesizing 4-nitrocatechol from nitrobenzene. Fishman, A., Tao, Y., Bentley, W.E., Wood, T.K. Biotechnol. Bioeng. (2004) [Pubmed]
  17. Both cytochromes P450 2E1 and 3A are involved in the O-hydroxylation of p-nitrophenol, a catalytic activity known to be specific for P450 2E1. Zerilli, A., Ratanasavanh, D., Lucas, D., Goasduff, T., Dréano, Y., Menard, C., Picart, D., Berthou, F. Chem. Res. Toxicol. (1997) [Pubmed]
  18. 4-Nitrocatechol production from rho-nitrophenol by rat liver. Chrastil, J., Wilson, J.T. J. Pharmacol. Exp. Ther. (1975) [Pubmed]
  19. Arylsulfatase B deficiency in Maroteaux-Lamy syndrome: Cellular studies and carrier identification. Beratis, N.G., Turner, B.M., Weiss, R., Hirschhorn, K. Pediatr. Res. (1975) [Pubmed]
  20. Assessment of catechol induction and glucuronidation in rat liver microsomes. Elovaara, E., Mikkola, J., Luukkanen, L., Antonio, L., Fournel-Gigleux, S., Burchell, B., Magdalou, J., Taskinen, J. Drug Metab. Dispos. (2004) [Pubmed]
  21. Simultaneous determination of 4-nitroanisole, 4-nitrophenol, and 4-nitrocatechol by phase-sensitive ac polarography. Burgschat, H., Netter, K.J. Journal of pharmaceutical sciences. (1977) [Pubmed]
  22. Characterization of catechol glucuronidation in rat liver. Antonio, L., Grillasca, J.P., Taskinen, J., Elovaara, E., Burchell, B., Piet, M.H., Ethell, B., Ouzzine, M., Fournel-Gigleux, S., Magdalou, J. Drug Metab. Dispos. (2002) [Pubmed]
  23. The role of the Sphingomonas species UG30 pentachlorophenol-4-monooxygenase in p-nitrophenol degradation. Leung, K.T., Campbell, S., Gan, Y., White, D.C., Lee, H., Trevors, J.T. FEMS Microbiol. Lett. (1999) [Pubmed]
  24. Isolation and characterization of a bacterial strain of the genus Ochrobactrum with methyl parathion mineralizing activity. Qiu, X.H., Bai, W.Q., Zhong, Q.Z., Li, M., He, F.Q., Li, B.T. J. Appl. Microbiol. (2006) [Pubmed]
  25. Validation of a HPLC method for the determination of p-nitrophenol hydroxylase activity in rat hepatic microsomes. Elbarbry, F., Wilby, K., Alcorn, J. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. (2006) [Pubmed]
  26. Isoniazid-induced hepatotoxicity in rat hepatocytes of gel entrapment culture. Shen, C., Zhang, H., Zhang, G., Meng, Q. Toxicol. Lett. (2006) [Pubmed]
  27. Arylsulfatase A in urine of patients with urothelial tumors. Arenas, J., Mayor, J., Gella, F.J., Fraile, B., Bornstein, B., Jarillo, M.D., Martinez, A., Santos, I. Clin. Biochem. (1988) [Pubmed]
  28. Structural and thermochemical characterization of lipoxygenase-catechol complexes. Pham, C., Jankun, J., Skrzypczak-Jankun, E., Flowers, R.A., Funk, M.O. Biochemistry (1998) [Pubmed]
  29. Properties of a complex of Fe(III)-soybean lipoxygenase-1 and 4-nitrocatechol. Spaapen, L.J., Verhagen, J., Veldink, G.A., Vliegenthart, J.F. Biochim. Biophys. Acta (1980) [Pubmed]
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