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

General Information of Drug (ID: DR0006)
Drug Name
Naphthoquinone beta
Synonyms
Beta-Naphthoquinone; Naphthalene-1,2-dione; 1,2-Naphthoquinone; o-Naphthoquinone; KETQAJRQOHHATG-UHFFFAOYSA-N; NAPHTHALENEDIONE; .beta.-Naphthoquinone; 1,2-Dihydro-1,2-diketo-naphthalene; 1,2-NAPHTHOQUINONE; 1,2-Naftochinon; 1,2-Naftochinon [Czech]; 1,2-Naphthalenedione; 1,2-Naphthaquinone; 1,2-Naphthoquinone, 95%, tech.; 1,2-dihydronaphthalene-1,2-dione; 524-42-5; 804K62F61Q; AI3-14930; BRN 0606546; C10H6O2; CCRIS 1558; CHEBI:34055; CHEMBL52347; EINECS 208-360-2; HSDB 2036; MFCD00001698; MLS000069467; NSC 9831; SMR000059112; UNII-804K62F61Q
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 158.15 Topological Polar Surface Area 34.1
Heavy Atom Count 12 Rotatable Bond Count 0
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
10667
ChEBI ID
CHEBI:34055
CAS Number
524-42-5
TTD Drug ID
D0W9VA
Formula
C10H6O2
Canonical SMILES
C1=CC=C2C(=C1)C=CC(=O)C2=O
InChI
1S/C10H6O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6H
InChIKey
KETQAJRQOHHATG-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
Naphthoquinone beta Metabolite A13 DM003939 N. A. Unclear 1 [5]
Naphthoquinone beta Metabolite A17 DM003943 N. A. Unclear 1 [5]
Naphthoquinone beta Metabolite A9 DM003936 N. A. Unclear 1 [5]
Naphthoquinone beta Metabolite A11 DM003937 N. A. Unclear 2 [5]
Naphthoquinone beta Metabolite A14 DM003940 N. A. Unclear 2 [5]
Naphthoquinone beta Metabolite A15 DM003941 N. A. Unclear 2 [5]
Naphthoquinone beta Metabolite A16 DM003942 N. A. Unclear 2 [5]
Naphthoquinone beta Metabolite A12 DM003938 N. A. Unclear 3 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004301 Naphthoquinone beta Naphthoquinone beta Metabolite A9 Unclear Unclear [5]
MR004304 Naphthoquinone beta Naphthoquinone beta Metabolite A13 Unclear Unclear [5]
MR004308 Naphthoquinone beta Naphthoquinone beta Metabolite A17 Unclear Unclear [5]
MR004305 Naphthoquinone beta Metabolite A13 Naphthoquinone beta Metabolite A14 Unclear Unclear [5]
MR004306 Naphthoquinone beta Metabolite A13 Naphthoquinone beta Metabolite A15 Unclear Unclear [5]
MR004307 Naphthoquinone beta Metabolite A13 Naphthoquinone beta Metabolite A16 Unclear Unclear [5]
MR004302 Naphthoquinone beta Metabolite A9 Naphthoquinone beta Metabolite A11 Unclear Unclear [5]
MR004303 Naphthoquinone beta Metabolite A11 Naphthoquinone beta Metabolite A12 Unclear Unclear [5]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Dicarbonyl/L-xylulose reductase (DCXR) DME0412 Homo sapiens
DCXR_HUMAN
1.1.1.10
[2]
NADPH:quinone reductase (CRYZ) DME0468 Homo sapiens
QOR_HUMAN
1.6.5.5
[3]
Sepiapterin reductase (SPR) DME0570 Homo sapiens
SPRE_HUMAN
1.1.1.153
[4]
References
1 Planarity and constraint of the carbonyl groups in 1,2-diones are determinants for selective inhibition of human carboxylesterase 1. J Med Chem. 2007 Nov 15;50(23):5727-34.
2 Diacetyl/l-xylulose reductase mediates chemical redox cycling in lung epithelial cells. Chem Res Toxicol. 2017 Jul 17;30(7):1406-1418.
3 Effect of superoxide dismutase on the autoxidation of various hydroquinones--a possible role of superoxide dismutase as a superoxide:semiquinone oxidoreductase. Free Radic Biol Med. 1988;5(2):71-9.
4 Sepiapterin reductase mediates chemical redox cycling in lung epithelial cells. J Biol Chem. 2013 Jun 28;288(26):19221-37.
5 Formation of Bulky DNA Adducts by Non-Enzymatic Production of 1,2-Naphthoquinone-Epoxide from 1,2-Naphthoquinone under Physiological Conditions

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