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MolPort-001-757-275
Also known as: 554-84-7, M-nitrophenol, 3-hydroxynitrobenzene, Phenol, 3-nitro-, M-hydroxynitrobenzene, Phenol, m-nitro-
Molecular Formula
C6H5NO3
Molecular Weight
139.11  g/mol
InChI Key
RTZZCYNQPHTPPL-UHFFFAOYSA-N
FDA UNII
T6P4T52V9W

1 2D Structure

MolPort-001-757-275

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-nitrophenol
2.1.2 InChI
InChI=1S/C6H5NO3/c8-6-3-1-2-5(4-6)7(9)10/h1-4,8H
2.1.3 InChI Key
RTZZCYNQPHTPPL-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=CC(=C1)O)[N+](=O)[O-]
2.2 Other Identifiers
2.2.1 UNII
T6P4T52V9W
2.3 Synonyms
2.3.1 MeSH Synonyms

1. M-nitrophenol

2.3.2 Depositor-Supplied Synonyms

1. 554-84-7

2. M-nitrophenol

3. 3-hydroxynitrobenzene

4. Phenol, 3-nitro-

5. M-hydroxynitrobenzene

6. Phenol, M-nitro-

7. M-nitrofenol

8. Meta-nitrophenol

9. 3-nitro-phenol

10. 1-hydroxy-3-nitrobenzene

11. Nsc 1551

12. T6p4t52v9w

13. Chebi:34346

14. Nsc-1551

15. M-nitrofenol [czech]

16. Crump Leather-lasting Dressing

17. Ccris 2315

18. Hsdb 1337

19. Einecs 209-073-5

20. Unii-t6p4t52v9w

21. Ai3-08825

22. 5-nitrophenol

23. 3-nitro Phenol

24. Mfcd00007240

25. Nitrophenol, 3-

26. Wln: Wnr Cq

27. Dsstox_cid_5765

28. M-nitrophenol [mi]

29. Dsstox_rid_77916

30. Dsstox_gsid_25765

31. Schembl50135

32. Mls002415747

33. 3-nitrophenol [hsdb]

34. Bidd:er0534

35. Chembl13888

36. Sr-1c3

37. 3-nitrophenol, Puriss., 99%

38. Dtxsid2025765

39. Schembl13815837

40. Nsc1551

41. Hms3039h09

42. Str00679

43. Zinc1576887

44. Tox21_200022

45. Stk290830

46. Akos000119831

47. Akos015831340

48. Akos024268500

49. M-nitrophenol [un1663] [poison]

50. 3-nitrophenol, Reagentplus(r), 99%

51. Ac-3123

52. Ncgc00090900-01

53. Ncgc00090900-02

54. Ncgc00257576-01

55. Cas-554-84-7

56. Smr001370910

57. Db-024131

58. 3-nitrophenol 100 Microg/ml In Cyclohexane

59. 3-nitrophenol, Purum, >=98.0% (hplc)

60. Ft-0616257

61. N0217

62. N-3595

63. A830666

64. Ae-562/40296193

65. Q3598793

66. Z57160187

67. F0001-1455

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 139.11 g/mol
Molecular Formula C6H5NO3
XLogP32
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Exact Mass139.026943022 g/mol
Monoisotopic Mass139.026943022 g/mol
Topological Polar Surface Area66 Ų
Heavy Atom Count10
Formal Charge0
Complexity131
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Absorption, Distribution and Excretion

The retention of radiolabeled 3-nitrophenol by various tissues of frog and crayfish following admin of 5 mg/kg via the lymph sac in frog and 3 mg/kg via pericardial injection in crayfish gradually decr in each organ except the gall bladder of the frog and the gut contents. In frogs, biliary excretion was minor compared with renal elimination, whereas in crayfish the gills represented the major route of excretion.

PMID:6974576 Nagel R, Urich K; Bull Environ Contam Toxicol 26 (3): 289-94 (1981)


The permeation of nitrophenols through epidermal cells from newborn rat skin cultured on type IV collagen-coated Millipore filters was studied under various conditions. The order of permeation through the cultured skin cells was found to be p-> m- > o-nitrophenol at both 10 and approx 37 C. This order was the same as that of their affinities to isolated skin cells. The permeation of nitrophenols was not inhibited by the inhibitors of energy transduction 2-deoxyglucose and NaN3. These results suggest that the permeation of nitrophenols across a cultured cell layer occurs by simple diffusion. The order of permeation of nitrophenols across newborn abdominal epidermis was exactly the opposite of that of their permeation across a cultured cell layer.

PMID:2076563 Ohkura K et al; Chem Pharm Bull (TOKYO) 38 (10):2788-91 (1990)


4.2 Metabolism/Metabolites

Yields m-aminophenol, 4-nitrocatechol, m-nitrophenyl-beta-d-glucuronide, m-nitrophenyl sulfate, & nitroquinol in rabbit.

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. N-17


M-nitrophenyl-beta-d-glucoside in fly. Yields m-nitroanisole in guinea pig. /From table/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. N-17


The metabolism of nitrobenzene in male Fischer-344 rats, CD rats, and B6C3F1 mice was examined. m-Nitrophenol was one of the metabolites which was excreted as the sulfate ester by Fischer-344 rats and sulfate ester and glucuronide by CD rats. B6C3F1 mice excreted the same metabolites (except the glucuronide of m-nitrophenol) in the urine as did CD rats and also excreted p-aminophenol sulfate. In all 3 animal strains, urinary excretion of nitrobenzene metabolites peaked 12-24 hr after oral admin of nitrobenzene.

PMID:6836574 Rickert DE et al; Toxicol Appl Pharmacol 67 (2): 206-14 (1983)


In vivo studies with nitrophenols ... meta-& para-nitrophenol are reduced more readily than the ortho isomer ...

Testa, B. and P. Jenner. Drug Metabolism: Chemical & Biochemical Aspects. New York: Marcel Dekker, Inc., 1976., p. 125


For more Metabolism/Metabolites (Complete) data for 3-NITROPHENOL (10 total), please visit the HSDB record page.


4.3 Mechanism of Action

Nitrophenols interfere with normal metabolism by uncoupling oxidative phosphorylation. For the mononitrophenols, the order of severity of effects is 4->3-> 2-nitrophenol.

USEPA; Nitrophenols: Hazard Profile (Draft) p.18 (1980)


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