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
CHEMBL34055
CAS Number
524-42-5
TTD ID
D0W9VA
INTEDE ID
DR0006
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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]
Dehydrogenase/reductase SDR family member 7 (DHRS7) OTV729DT DHRS7_HUMAN Biotransformations [8]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [9]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [10]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [10]
Protein c-Fos (FOS) OTJBUVWS FOS_HUMAN Protein Interaction/Cellular Processes [10]
Transient receptor potential cation channel subfamily A member 1 (TRPA1) OTRDIR5M TRPA1_HUMAN Gene/Protein Processing [11]
Transient receptor potential cation channel subfamily V member 3 (TRPV3) OTC57YC6 TRPV3_HUMAN Gene/Protein Processing [12]
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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 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.
9 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.
10 Activation of EGFR/MEK/ERK/AP-1 signaling mediated by 1,2-naphthoquinone, an atmospheric electrophile, in human pulmonary A549 cells. J Toxicol Sci. 2013;38(5):793-7. doi: 10.2131/jts.38.793.
11 Electrophilic components of diesel exhaust particles (DEP) activate transient receptor potential ankyrin-1 (TRPA1): a probable mechanism of acute pulmonary toxicity for DEP. Chem Res Toxicol. 2011 Jun 20;24(6):950-9. doi: 10.1021/tx200123z. Epub 2011 May 25.
12 Activation of TRPV3 by Wood Smoke Particles and Roles in Pneumotoxicity. Chem Res Toxicol. 2018 May 21;31(5):291-301. doi: 10.1021/acs.chemrestox.7b00336. Epub 2018 Apr 30.