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
UNII
TRY8UD4E2H
DrugBank ID
DB16249
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.