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

General Information of Drug (ID: DR2038)
Drug Name
Aminophenol
Synonyms
Benzofur GG; Fouramine OP; Nako Yellow 3GA; Nako Yellow ga; O-AMINOPHENOL; ORTHO AMINO PHENOL; Paradone Olive Green B; Pelagol 3GA; Pelagol Grey GG; 2-Aminophenol; BASF ursol 3GA; Phenol, 2-amino-; Phenol, o-amino-; Questiomycin B; Zoba 3GA; o-Hydroxyaniline; o-Hydroxyphenylamine; ortho-aminophenol; 1-Amino-2-hydroxybenzene; 1-Hydroxy-2-aminobenzene; 2-Amino-1-hydroxybenzene; 2-Aminobenzenol; 2-Hydroxyanaline; 2-Hydroxyaniline; 2-amino-phenol; 95-55-6; C.I. 76520; C.I. Oxidation Base 17; CI Oxidation Base 17; NSC 1534
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 109.13 Topological Polar Surface Area 46.2
Heavy Atom Count 8 Rotatable Bond Count 0
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
5801
ChEBI ID
CHEBI:18112
CAS Number
95-55-6
Formula
C6H7NO
Canonical SMILES
C1=CC=C(C(=C1)N)O
InChI
1S/C6H7NO/c7-5-3-1-2-4-6(5)8/h1-4,8H,7H2
InChIKey
CDAWCLOXVUBKRW-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-aminomuconic 6-semialdehyde DM003799
5280625
Unclear 1 [2]
O-quinoimine DM003805 N. A. Unclear 1 [4]
2-amino-phenoxazine-3-one DM003806 N. A. Unclear 2 [4]
2-Aminomuconic acid DM003800
5459864
Unclear 2 [2]
Picolinic acid DM003807
1018
Unclear 2 [2]
2-Amino-2,4-pentadienoic acid DM003801
74926715
Unclear 3 [2]
2-Oxopent-4-enoic acid DM003802
976
Unclear 4 [2]
4-Hydroxy-2-oxovaleric acid DM003803
124
Unclear 5 [2]
Acetaldehyde DM003092
177
Unclear 6 [2]
Pyruvic acid DM002137
1060
Unclear 6 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004155 Aminophenol 2-aminomuconic 6-semialdehyde Unclear amnB [2]
MR004162 Aminophenol O-quinoimine Unclear Unclear [4]
MR004156 2-aminomuconic 6-semialdehyde 2-Aminomuconic acid Unclear Unclear [2]
MR004164 2-aminomuconic 6-semialdehyde Picolinic acid Unclear Unclear [2]
MR004163 O-quinoimine 2-amino-phenoxazine-3-one Unclear Unclear [4]
MR004157 2-Aminomuconic acid 2-Amino-2,4-pentadienoic acid Unclear Unclear [2]
MR004158 2-Amino-2,4-pentadienoic acid 2-Oxopent-4-enoic acid Unclear Unclear [2]
MR004159 2-Oxopent-4-enoic acid 4-Hydroxy-2-oxovaleric acid Unclear Unclear [2]
MR004160 4-Hydroxy-2-oxovaleric acid Acetaldehyde Unclear Unclear [2]
MR004161 4-Hydroxy-2-oxovaleric acid Pyruvic acid Unclear Unclear [2]
⏷ Show the Full List of 10 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
2-aminophenol 1,6-dioxygenase beta subunit (amnB) DMEN149 Pseudomonas sp
AMNB_PSESP
1.13.11.74
[2]
Sulfotransferase 1B1 (SULT1B1) DME0380 Homo sapiens
ST1B1_HUMAN
2.8.2.1
[3]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Sulfotransferase 1B1 (SULT1B1) DME0380 Km = 0.009 microM
ST1B1_HUMAN
[3]
References
1 DrugBank 5.0: a major update to the DrugBank database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D1074-D1082. (id: DB01726)
2 Metabolism of 2-aminophenol by Pseudomonas sp. AP-3: modified meta-cleavage pathway
3 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.
4 Mechanism of o-aminophenol metabolism in human erythrocytes

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