Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2760)
Drug Name
Nitrobenzoate
Synonyms P-nitrobenzoate; 4-Nitrobenzoate; OTLNPYWUJOZPPA-UHFFFAOYSA-M; SCHEMBL187708; p-nitrophenylformate; 4-nitrobenzoate; 4NBZate; 7227-54-5; BDBM50340073; CHEBI:142863; CHEMBL1762655; DTXSID20403094
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 166.11 Topological Polar Surface Area 86
Heavy Atom Count 12 Rotatable Bond Count 0
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
4419940
ChEBI ID
CHEBI:142863
CAS Number
7227-54-5
Formula
C7H4NO4-
Canonical SMILES
C1=CC(=CC=C1C(=O)[O-])[N+](=O)[O-]
InChI
1S/C7H5NO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4H,(H,9,10)/p-1
InChIKey
OTLNPYWUJOZPPA-UHFFFAOYSA-M
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
4-hydroxylaminobenzoate DM003984
11137507
Reduction - Reduction 1 [6]
Protocatechuate DM002607
72
Unclear 2 [7]
Alpha-hydroxy-gamma-carboxymuconic semialdehyde DM003997 N. A. Other reaction - Ring cleavage reaction 3 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR012892 Nitrobenzoate 4-hydroxylaminobenzoate Reduction - Reduction Unclear [6]
MR012893 4-hydroxylaminobenzoate Protocatechuate Unclear Unclear [7]
MR012894 Protocatechuate Alpha-hydroxy-gamma-carboxymuconic semialdehyde Other reaction - Ring cleavage reaction Unclear [7]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Nitroreductase (NTR) DME1968 Salmonella typhimurium
A0A5K1UB29_SALTM
1.5.1.39
[2] , [3]
Oxygen-insensitive NADPH nitroreductase A (nfsA) DME1586 Pseudomonas putida
Q7B4Y3_PSEPU
1.5.1.38
[4] , [5]
References
1 4-Nitrobenzoate inhibits coenzyme Q biosynthesis in mammalian cell cultures. Nat Chem Biol. 2010 Jul;6(7):515-7.
2 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.
3 Prenatal diagnosis of junctional epidermolysis bullosa Herlitz type. Lancet. 1989 Oct 28;2(8670):1035-6. Letter
4 PnrA, a new nitroreductase-family enzyme in the TNT-degrading strain Pseudomonas putida JLR11. Environ Microbiol. 2005 Aug;7(8):1211-9.
5 A Lethal Case of Pseudomonas putida Bacteremia Due to Soft Tissue Infection. Infect Dis Clin Pract (Baltim Md). 2013 May;21(3):147-213.
6 Longevity determines sizes of an adult intertidal barnacle
7 Biodegradation of 4-nitrotoluene by Pseudomonas sp. strain 4NT

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