Details of the Drug

General Information of Drug (ID: DMTCMH7)

Drug Name
1,4-Naphthoquinone
Synonyms
1,4-NAPHTHOQUINONE; 130-15-4; naphthalene-1,4-dione; p-Naphthoquinone; NAPHTHOQUINONE; alpha-Naphthoquinone; 1,4-Naphthylquinone; USAF CY-10; 1,4-dihydronaphthalene-1,4-dione; 1,4-Dihydro-1,4-diketonaphthalene; 1,4-Naftochinon; RCRA waste number U166; UNII-RBF5ZU7R7K; NSC 9583; 1,4-Naftochinon [Czech]; 1,4-Naphthaquinone; CCRIS 5424; HSDB 2037; EINECS 204-977-6; RBF5ZU7R7K; RCRA waste no U166; CHEMBL55934; AI3-24292; NQ-1; CHEBI:27418; NSC9583; FRASJONUBLZVQX-UHFFFAOYSA-N; MFCD00001676; 1,4-naphtho-quinone
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) 1.7
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C10H6O2
IUPAC Name
naphthalene-1,4-dione
Canonical SMILES
C1=CC=C2C(=O)C=CC(=O)C2=C1
InChI
InChI=1S/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H
InChIKey
FRASJONUBLZVQX-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
8530
ChEBI ID
CHEBI:27418
CAS Number
130-15-4
TTD ID
D0DQ6Z
INTEDE ID
DR2714

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Indoleamine 2,3-dioxygenase 1 (IDO1) TTZJYKH I23O1_HUMAN Inhibitor [2]
Plasmodium Dihydroorotate dehydrogenase (Malaria DHOdehase) TT3PQ2Y PYRD_PLAF7 Inhibitor [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Sulfide-quinone reductase (SQR)
Main DME 		DEGLTNR SQRD_ACIF2 Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [4]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [4]
Aryl hydrocarbon receptor (AHR) OTFE4EYE AHR_HUMAN Protein Interaction/Cellular Processes [5]
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [6]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Protein Interaction/Cellular Processes [4]
Caspase-8 (CASP8) OTA8TVI8 CASP8_HUMAN Gene/Protein Processing [7]
Cytochrome P450 1A1 (CYP1A1) OTE4EFH8 CP1A1_HUMAN Gene/Protein Processing [5]
Cytochrome P450 1A2 (CYP1A2) OTLLBX48 CP1A2_HUMAN Gene/Protein Processing [8]
Cytochrome P450 1B1 (CYP1B1) OTYXFLSD CP1B1_HUMAN Regulation of Drug Effects [9]
Cytochrome P450 2B6 (CYP2B6) OTOYO4S7 CP2B6_HUMAN Regulation of Drug Effects [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Kinetics of inhibition of human and rat dihydroorotate dehydrogenase by atovaquone, lawsone derivatives, brequinar sodium and polyporic acid. Chem Biol Interact. 2000 Jan 3;124(1):61-76.
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 The quinone-binding site of Acidithiobacillus ferrooxidans sulfide: quinone oxidoreductase controls both sulfide oxidation and quinone reduction. Biochem Cell Biol. 2016 Apr;94(2):159-66.
4 New naphthalene derivatives induce human lung cancer A549?cell apoptosis via ROS-mediated MAPKs, Akt, and STAT3 signaling pathways. Chem Biol Interact. 2019 May 1;304:148-157. doi: 10.1016/j.cbi.2019.03.004. Epub 2019 Mar 11.
5 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.
6 Genotoxic and inflammatory effects of organic extracts from traffic-related particulate matter in human lung epithelial A549 cells: the role of quinones. Toxicol In Vitro. 2013 Mar;27(2):922-31. doi: 10.1016/j.tiv.2013.01.008. Epub 2013 Jan 16.
7 Cytotoxic activity of naphthoquinones with special emphasis on juglone and its 5-O-methyl derivative. Chem Biol Interact. 2010 Mar 30;184(3):439-48. doi: 10.1016/j.cbi.2010.01.041. Epub 2010 Feb 4.
8 In vitro toxicity of naphthalene, 1-naphthol, 2-naphthol and 1,4-naphthoquinone on human CFU-GM from female and male cord blood donors. Toxicol In Vitro. 2008 Sep;22(6):1555-61.
9 In vitro metabolism of naphthalene by human liver microsomal cytochrome P450 enzymes. Drug Metab Dispos. 2006 Jan;34(1):176-83. doi: 10.1124/dmd.105.005785. Epub 2005 Oct 21.