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], [2]

• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 158.15
  Topological Polar Surface Area (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]

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] The fight against drug-resistant malaria: novel plasmodial targets and antimalarial drugs. Curr Med Chem. 2008;15(2):161-71.
• [5] Identification and characterization of potential new therapeutic targets in inflammatory and autoimmune diseases. Eur J Biochem. 1999 Dec;266(3):1184-91.
• [6] Expression and characterization of E. coli-produced soluble, functional human dihydroorotate dehydrogenase: a potential target for immunosuppression. J Mol Microbiol Biotechnol. 1999 Aug;1(1):183-8.
• [7] Inhibitor binding in a class 2 dihydroorotate dehydrogenase causes variations in the membrane-associated N-terminal domain. Protein Sci. 2004 Apr;13(4):1031-42.
• [8] How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
• [9] Antimalarial activity of orotate analogs that inhibit dihydroorotase and dihydroorotate dehydrogenase. Biochem Pharmacol. 1992 Mar 17;43(6):1295-301.
• [10] Structure-activity relationships of pyrimidines as dihydroorotate dehydrogenase inhibitors. Biochem Pharmacol. 1988 Oct 15;37(20):3807-16.
• [11] Interactions between nitric oxide and indoleamine 2,3-dioxygenase. Biochemistry. 2006 Jul 18;45(28):8527-38.
• [12] Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
• [13] Incyte. Product Development Pipeline.
• [14] ClinicalTrials.gov (NCT03641794) Indoleamine 2,3-Dioxygenase (IDO) Inhibitor in Healthy Volunteers. U.S. National Institutes of Health.
• [15] Discovery of cyanopyridine scaffold as novel indoleamine-2,3-dioxygenase 1 (IDO1) inhibitors through virtual screening and preliminary hit optimisation. J Enzyme Inhib Med Chem. 2019 Dec;34(1):250-263.
• [16] Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)