Details of the Drug

General Information of Drug (ID: DMYXELH)

Drug Name
1,2-NAPHTHOQUINONE
Synonyms
1,2-NAPHTHOQUINONE; 524-42-5; 1,2-Naphthalenedione; naphthalene-1,2-dione; o-Naphthoquinone; beta-Naphthoquinone; 1,2-Naphthaquinone; 1,2-Naftochinon; .beta.-Naphthoquinone; 1,2-Naftochinon [Czech]; CCRIS 1558; UNII-804K62F61Q; HSDB 2036; 1,2-dihydronaphthalene-1,2-dione; NSC 9831; EINECS 208-360-2; 1,2-Dihydro-1,2-diketo-naphthalene; BRN 0606546; CHEMBL52347; MLS000069467; AI3-14930; CHEBI:34055; C10H6O2; KETQAJRQOHHATG-UHFFFAOYSA-N; 804K62F61Q; SMR000059112; 1,2-Naphthoquinone, 95%, tech.; NAPHTHALENEDIONE; b-naphthoquinone
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 158.15
Logarithm of the Partition Coefficient (xlogp) 1.5
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C10H6O2
IUPAC Name
naphthalene-1,2-dione
Canonical SMILES
C1=CC=C2C(=C1)C=CC(=O)C2=O
InChI
InChI=1S/C10H6O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6H
InChIKey
KETQAJRQOHHATG-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
10667
ChEBI ID
CHEBI:34055
CAS Number
524-42-5
TTD ID
D0W9VA
INTEDE ID
DR0006

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Acetylcholinesterase (AChE) TT1RS9F ACES_HUMAN Inhibitor [1]
Cholinesterase (BCHE) TTEB0GD CHLE_HUMAN Inhibitor [1]
Indoleamine 2,3-dioxygenase 1 (IDO1) TTZJYKH I23O1_HUMAN Inhibitor [2]
Liver carboxylesterase (CES1) TTMF541 EST1_HUMAN Inhibitor [1]
PTPN1 messenger RNA (PTPN1 mRNA) TTELIN2 PTN1_HUMAN Inhibitor [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
NADPH:quinone reductase (CRYZ) DE8RYV5 QOR_HUMAN Substrate [4]
Dicarbonyl/L-xylulose reductase (DCXR) DE3FEV8 DCXR_HUMAN Substrate [5]
Sepiapterin reductase (SPR) DEJVDAT SPRE_HUMAN Substrate [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Aflatoxin B1 aldehyde reductase member 2 (AKR7A2) OTGEDDM2 ARK72_HUMAN Biotransformations [7]
Aldo-keto reductase family 1 member A1 (AKR1A1) OTZT9NOW AK1A1_HUMAN Biotransformations [7]
Aldo-keto reductase family 1 member B1 (AKR1B1) OTRX72TH ALDR_HUMAN Biotransformations [7]
Cytochrome P450 1A1 (CYP1A1) OTE4EFH8 CP1A1_HUMAN Gene/Protein Processing [8]
Dehydrogenase/reductase SDR family member 7 (DHRS7) OTV729DT DHRS7_HUMAN Biotransformations [9]
DNA topoisomerase 2-alpha (TOP2A) OT6LPS08 TOP2A_HUMAN Gene/Protein Processing [10]
DNA topoisomerase 2-beta (TOP2B) OTDHKQZ8 TOP2B_HUMAN Gene/Protein Processing [10]
Epidermal growth factor receptor (EGFR) OTAPLO1S EGFR_HUMAN Post-Translational Modifications [11]
Glyceraldehyde-3-phosphate dehydrogenase (GAPDH) OTBPMIMW G3P_HUMAN Gene/Protein Processing [12]
Heme oxygenase 1 (HMOX1) OTC1W6UX HMOX1_HUMAN Gene/Protein Processing [13]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Acetylcholinesterase (AChE) DTT ACHE 6.39E-02 -1.07 -1.15
Sepiapterin reductase (SPR) DME SPR 2.59E-02 3.51E-01 9.51E-01
NADPH:quinone reductase (CRYZ) DME CRYZ 4.18E-01 2.63E-02 4.31E-02
Dicarbonyl/L-xylulose reductase (DCXR) DME DCXR 1.58E-01 7.19E-02 2.50E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

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 Indoleamine 2,3-dioxygenase is the anticancer target for a novel series of potent naphthoquinone-based inhibitors. J Med Chem. 2008 Mar 27;51(6):1706-18.
3 Synthesis and PTP1B inhibition of 1,2-naphthoquinone derivatives as potent anti-diabetic agents. Bioorg Med Chem Lett. 2002 Aug 5;12(15):1941-6.
4 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.
5 Diacetyl/l-xylulose reductase mediates chemical redox cycling in lung epithelial cells. Chem Res Toxicol. 2017 Jul 17;30(7):1406-1418.
6 Sepiapterin reductase mediates chemical redox cycling in lung epithelial cells. J Biol Chem. 2013 Jun 28;288(26):19221-37.
7 Major differences exist in the function and tissue-specific expression of human aflatoxin B1 aldehyde reductase and the principal human aldo-keto reductase AKR1 family members. Biochem J. 1999 Oct 15;343 Pt 2(Pt 2):487-504.
8 Quinone-mediated induction of cytochrome P450 1A1 in HepG2 cells through increased interaction of aryl hydrocarbon receptor with aryl hydrocarbon receptor nuclear translocator. J Toxicol Sci. 2016;41(6):775-781.
9 Biochemical properties of human dehydrogenase/reductase (SDR family) member 7. Chem Biol Interact. 2014 Jan 25;207:52-7. doi: 10.1016/j.cbi.2013.11.003. Epub 2013 Nov 16.
10 1,2-Naphthoquinone as a Poison of Human Type II Topoisomerases. Chem Res Toxicol. 2021 Apr 19;34(4):1082-1090. doi: 10.1021/acs.chemrestox.0c00492. Epub 2021 Mar 24.
11 Activation of PTP1B/EGFR signaling and cytotoxicity during combined exposure to ambient electrophiles in A431 cells. J Toxicol Sci. 2021;46(4):177-185. doi: 10.2131/jts.46.177.
12 GSH-mediated S-transarylation of a quinone glyceraldehyde-3-phosphate dehydrogenase conjugate. Chem Res Toxicol. 2011 Nov 21;24(11):1836-44. doi: 10.1021/tx200025y. Epub 2011 Sep 1.
13 Linking oxidative events to inflammatory and adaptive gene expression induced by exposure to an organic particulate matter component. Environ Health Perspect. 2012 Feb;120(2):267-74.