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

General Information of Drug (ID: DR2317)
Drug Name
Aniline
Synonyms
ANILINE; Aminobenzene; Aminophen; Anilin; Anilin [Czech]; Anilina; Anilina [Italian, Polish]; Aniline (and salts); Aniline and homologs; Aniline and homologues; Aniline oil; Aniline reagent; Anyvim; Arylamine; Benzenamine; Benzene, amino; Benzeneamine; Benzidam; Blue Oil; Cyanol; Krystallin; Kyanol; Phenylamine; RCRA waste no. U012; Rcra waste number U012; UN 1547; 62-53-3; C.I. 76000; C.I. Oxidation Base 1; CCRIS 44; CI Oxidation Base 1; Caswell No. 051C; HSDB 43; Huile D'aniline; Huile d'aniline [French]; NCI-C03736; UNII-SIR7XX2F1K
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 93.13 Topological Polar Surface Area 26
Heavy Atom Count 7 Rotatable Bond Count 0
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
6115
ChEBI ID
CHEBI:17296
CAS Number
62-53-3
Formula
C6H7N
Canonical SMILES
C1=CC=C(C=C1)N
InChI
1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2
InChIKey
PAYRUJLWNCNPSJ-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
2-aminophenol DM004788
5801
Unclear 1 [5]
4-aminophenol DM003816
403
Oxidation - Aromatic hydroxylation 1 [5]
Acetanilide-d5 DM003813
129849362
Unclear 1 [6]
N-Hydroxyaniline DM003817
7518
Oxidation - N-oxidation 1 [7]
N-acetyl-4-aminophenol-d4 DM003814
12205925
Unclear 2 [6]
N-acetyl-4-aminophenol mercapturic acid-d3 DM003815 N. A. Unclear 3 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR012853 Aniline Acetanilide-d5 Unclear Unclear [6]
MR012856 Aniline 4-aminophenol Oxidation - Aromatic hydroxylation CYP2E1 [5]
MR012857 Aniline N-Hydroxyaniline Oxidation - N-oxidation CYP2E1 [7]
MR012858 Aniline 2-aminophenol Unclear Unclear [5]
MR012854 Acetanilide-d5 N-acetyl-4-aminophenol-d4 Unclear Unclear [6]
MR012855 N-acetyl-4-aminophenol-d4 N-acetyl-4-aminophenol mercapturic acid-d3 Unclear Unclear [6]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 102A1 (cyp102) DME1075 Bacillus megaterium
CPXB_BACMB
1.14.14.1
[2] , [3]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[4]
References
1 Aniline-based inhibitors of influenza H1N1 virus acting on hemagglutinin-mediated fusion. J Med Chem. 2018 Jan 11;61(1):98-118.
2 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.
3 The bacterial P450 BM3: a prototype for a biocatalyst with human P450 activities. Trends Biotechnol. 2007 Jul;25(7):289-98.
4 Cytochromes P450: a structure-based summary of biotransformations using representative substrates Drug Metab Rev. 2008;40(1):1-100. doi: 10.1080/03602530802309742.
5 Aniline and its metabolites generate free radicals in yeast
6 Human metabolism and excretion kinetics of aniline after a single oral dose
7 Aniline derivative-induced methemoglobin in rats

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