General Information of Drug (ID: DR1969)
Drug Name
Mononitrophenol
Synonyms
Paranitrofenol; Paranitrofenol [Dutch]; Paranitrofenolo; Paranitrofenolo [Italian]; Paranitrophenol; Paranitrophenol [French,German]; Phenol, 4-nitro-; 4-Nitrophenol; Niphen; Phenol, p-nitro-; RCRA waste no. U170; RCRA waste number U170; UN1663; p-Hydroxynitrobenzene; p-Nitrofenol; p-Nitrofenol [Czech]; p-nitrophenol; para-nitrophenol; 1-Hydroxy-4-nitrobenzene; 100-02-7; 4-Hydroxynitrobenzene; 4-Nitrofenol; 4-Nitrofenol [Dutch]; 4-nitro-phenol; Caswell No. 603; NCI-C55992; NSC 1317; PNP; UNII-Y92ZL45L4R
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 139.11 Topological Polar Surface Area 66
Heavy Atom Count 10 Rotatable Bond Count 0
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
980
ChEBI ID
CHEBI:16836
CAS Number
100-02-7
Formula
C6H5NO3
Canonical SMILES
C1=CC(=CC=C1[N+](=O)[O-])O
InChI
1S/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H
InChIKey
BTJIUGUIPKRLHP-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Mononitrophenol Metabolite A5 DM003922 N. A. Oxidation - Oxidationn 1 [5]
Mononitrophenol Metabolite A6 DM003923 N. A. Oxidation - Oxidationn 1 [11]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR012909 Mononitrophenol Mononitrophenol Metabolite A5 Oxidation - Oxidationn dyp1 ... [5]
MR012910 Mononitrophenol Mononitrophenol Metabolite A6 Oxidation - Oxidationn AAO ... [11]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aryl alcohol oxidase (AAO) DMEN184 . Not Available Not Available [2]
Cytochrome P450 102A1 (cyp102) DME1075 Bacillus megaterium
CPXB_BACMB
1.14.14.1
[3] , [4]
Dye-decolorizing peroxidase AauDyP1 (dyp1) DMEN182 Auricularia auricula-judae
DYP_AURAJ
1.11.1.19
[5]
Nitroreductase (NTR) DME1968 Salmonella typhimurium
A0A5K1UB29_SALTM
1.5.1.39
[6] , [7]
Sulfotransferase 1A2 (SULT1A2) DME0062 Homo sapiens
ST1A2_HUMAN
2.8.2.1
[8]
Sulfotransferase 1B1 (SULT1B1) DME0380 Homo sapiens
ST1B1_HUMAN
2.8.2.1
[9]
Versatile peroxidase VPL1 (vpl1) DMEN183 Pleurotus eryngii
VPL1_PLEER
1.11.1.16
[5]
⏷ Show the Full List of 7  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Sulfotransferase 1A2 (SULT1A2) DME0062 Km = 0.00775 microM
ST1A2_HUMAN
[8]
Sulfotransferase 1B1 (SULT1B1) DME0380 Km = 0.00036 microM
ST1B1_HUMAN
[10]
References
1 Catalytic reduction of 4-nitrophenol with gold nanoparticles synthesized by caffeic acid. Nanoscale Res Lett. 2017 Dec;12(1):7.
2 Mineralization of mono-nitrophenols by Bjerkandera adusta and Lentinus squarrosulus and their extracellular ligninolytic enzymes
3 Wild-type CYP102A1 as a biocatalyst: turnover of drugs usually metabolised by human liver enzymes. J Biol Inorg Chem. 2007 Mar;12(3):313-23.
4 The bacterial P450 BM3: a prototype for a biocatalyst with human P450 activities. Trends Biotechnol. 2007 Jul;25(7):289-98.
5 Different fungal peroxidases oxidize nitrophenols at a surface catalytic tryptophan
6 Purification and characterization of wild-type and mutant "classical" nitroreductases of Salmonella typhimurium. L33R mutation greatly diminishes binding of FMN to the nitroreductase of S. typhimurium. J Biol Chem. 1998 Sep 11;273(37):23922-8.
7 Prenatal diagnosis of junctional epidermolysis bullosa Herlitz type. Lancet. 1989 Oct 28;2(8670):1035-6. Letter
8 cDNA cloning and expression of a new form of human aryl sulfotransferase. Int J Biochem Cell Biol. 1996 May;28(5):565-71.
9 Comparison of 2-aminophenol and 4-nitrophenol as in vitro probe substrates for the major human hepatic sulfotransferase, SULT1A1, demonstrates improved selectivity with 2-aminophenol. Biochem Pharmacol. 2007 Jul 15;74(2):352-8.
10 Polychlorobiphenylols are selective inhibitors of human phenol sulfotransferase 1A1 with 4-nitrophenol as a substrate. Chem Biol Interact. 2006 Feb 25;159(3):235-46.
11 U. S. FDA Label -Mononitrophenol

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.