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

General Information of Drug (ID: DR0010)
Drug Name
Nitrobenzanthrone
Synonyms
3-Nitrobenzanthrone; LS-27953; O4OJW7BC7W; QAJOWHGESRCVLY-UHFFFAOYSA-N; SCHEMBL7168071; ZINC4370589; 17117-34-9; 3-Nitro-7H-benz(de)anthracen-7-one; 3-Nitro-7H-benzo[d,e]anthracen-7-one; 3-Nitrobenzantrone; 3-nitro-7H-benzo[de]anthracen-7-one; 3-nitrobenzo[b]phenalen-7-one; 7H-Benz(de)anthracen-7-one, 3-nitro-; AC1MCTJK; ACM17117349; CCRIS 9003; DTXSID60881271; FT-0710181; UNII-O4OJW7BC7W
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 275.26 Topological Polar Surface Area 62.9
Heavy Atom Count 21 Rotatable Bond Count 0
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
2825690
CAS Number
17117-34-9
Formula
C17H9NO3
Canonical SMILES
C1=CC=C2C(=C1)C3=C4C(=C(C=C3)[N+](=O)[O-])C=CC=C4C2=O
InChI
1S/C17H9NO3/c19-17-12-5-2-1-4-10(12)11-8-9-15(18(20)21)13-6-3-7-14(17)16(11)13/h1-9H
InChIKey
QAJOWHGESRCVLY-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-(2'-deoxyguanosin-N2-yl)-3-aminobenzanthrone DM003995
135921036
Unclear 1 [5]
3-OH-ABA DM003988 N. A. Reduction - Reduction 1 [5]
N-(2'-deoxyguanosin-8-yl)-3-aminobenzanthrone DM003996
135440443
Unclear 1 [5]
2-(2'-deoxyguanosin-N2-yl)-3-aminobenzanthrone DM003995
135921036
Unclear 2 [5]
3-Aco-ABA DM003991 N. A. Unclear 2 [5]
3-aminobenzanthrone DM003989
13143216
Reduction - Reduction 2 [5]
3-OS-ABA DM003993 N. A. Unclear 2 [5]
N-(2'-deoxyguanosin-8-yl)-3-aminobenzanthrone DM003996
135440443
Unclear 2 [5]
3-AcABA DM003990 N. A. Unclear 3 [5]
Nitrobenzanthrone Metabolite M3 DM003992 N. A. Unclear 3 [5]
Nitrobenzanthrone Metabolite M4 DM003994 N. A. Unclear 3 [5]
⏷ Show the Full List of 11  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004363 Nitrobenzanthrone 3-OH-ABA Reduction - Reduction CYP1A1 ... [5]
MR004372 Nitrobenzanthrone 2-(2'-deoxyguanosin-N2-yl)-3-aminobenzanthrone Unclear Unclear [5]
MR004373 Nitrobenzanthrone N-(2'-deoxyguanosin-8-yl)-3-aminobenzanthrone Unclear Unclear [5]
MR004364 3-OH-ABA 3-aminobenzanthrone Reduction - Reduction Unclear [5]
MR004366 3-OH-ABA 3-Aco-ABA Unclear nat [5]
MR004368 3-OH-ABA 3-OS-ABA Unclear SULT1A1 [5]
MR004370 3-OH-ABA 2-(2'-deoxyguanosin-N2-yl)-3-aminobenzanthrone Unclear NAT1 ... [5]
MR004371 3-OH-ABA N-(2'-deoxyguanosin-8-yl)-3-aminobenzanthrone Unclear NAT1 ... [5]
MR004367 3-Aco-ABA Nitrobenzanthrone Metabolite M3 Unclear Unclear [5]
MR004365 3-aminobenzanthrone 3-AcABA Unclear nat [5]
MR004369 3-OS-ABA Nitrobenzanthrone Metabolite M4 Unclear Unclear [5]
⏷ Show the Full List of 11 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Arylamine N-acetyltransferase (NAT) DME1099 Vibrio cholerae
A0A3P8LE58_TSUPA
2.3.1.5
[2]
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
N-acetyltransferase 1 (NAT1) DME0050 Homo sapiens
ARY1_HUMAN
2.3.1.5
[3]
N-acetyltransferase 2 (NAT2) DME0051 Homo sapiens
ARY2_HUMAN
2.3.1.5
[3]
Quinone reductase 1 (NQO1) DME0097 Homo sapiens
NQO1_HUMAN
1.6.5.2
[4]
Sulfotransferase 1A1 (SULT1A1) DME0008 Homo sapiens
ST1A1_HUMAN
2.8.2.1
[2]
Sulfotransferase 1A1 (SULT1A1) DME0008 Homo sapiens
ST1A1_HUMAN
2.8.2.1
[3]
Sulfotransferase 1A2 (SULT1A2) DME0062 Homo sapiens
ST1A2_HUMAN
2.8.2.1
[3]
⏷ Show the Full List of 9  DME(s)
References
1 The impact of p53 function on the metabolic activation of the carcinogenic air pollutant 3-nitrobenzanthrone and its metabolites 3-aminobenzanthrone and N-hydroxy-3-aminobenzanthrone in human cells. Mutagenesis. 2018 Oct 11;33(4):311-321.
2 Carcinogenic 3-nitrobenzanthrone but not 2-nitrobenzanthrone is metabolised to an unusual mercapturic acid in rats
3 Rat cytochromes P450 oxidize 3-aminobenzanthrone, a human metabolite of the carcinogenic environmental pollutant 3-nitrobenzanthrone
4 Dose-dependent response to 3-nitrobenzanthrone exposure in human urothelial cancer cells. Chem Res Toxicol. 2017 Oct 16;30(10):1855-1864.
5 Activation of 3-nitrobenzanthrone and its metabolites by human acetyltransferases, sulfotransferases and cytochrome P450 expressed in Chinese hamster V79 cells

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