Details of the Drug

General Information of Drug (ID: DMA86FL)

Drug Name

Avastin+/-Tarceva

Synonyms

Juglone; juglone; 481-39-0; 5-Hydroxy-1,4-naphthoquinone; 5-Hydroxy-1,4-naphthalenedione; Regianin; Juglon; Nucin; 5-Hydroxynaphthalene-1,4-dione; Walnut extract; 5-Hydroxynaphthoquinone; Akhnot; Yuglon; 8-Hydroxy-1,4-naphthoquinone; CI Natural Brown 7; 1,4-NAPHTHALENEDIONE, 5-HYDROXY-; 5-Hydroxy-p-naphthoquinone; 1,4-Naphthoquinone, 5-hydroxy-; CI 75500; Juglane; Jugnlon; Iuglon; Caswell No 515AA; 1,4-Naphthoquinone, 8-hydroxy-; 5-Hydroxy-1,4-naphthosemiquinone; 5-Hydroxy-1,4-naftochinon; UNII-W6Q80SK9L6; NSC 622948; NSC 153189; CCRIS; JUGLONE

Indication

Disease Entry	ICD 11	Status	REF
Non-small-cell lung cancer	2C25.Y	Phase 3	[1]
Nasopharyngeal carcinoma	2B6B	Investigative	[2]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

174.15

Logarithm of the Partition Coefficient (xlogp)

1.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C10H6O3
IUPAC Name: 5-hydroxynaphthalene-1,4-dione
Canonical SMILES: C1=CC2=C(C(=O)C=CC2=O)C(=C1)O
InChI: InChI=1S/C10H6O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,12H
InChIKey: KQPYUDDGWXQXHS-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 3806
ChEBI ID: CHEBI:15794
CAS Number: 481-39-0
TTD ID: D0C0NH

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Arachidonate 5-lipoxygenase (5-LOX)	TT2J34L	LOX5_HUMAN	Inhibitor	[3]
Dual specificity protein phosphatase 1 (DUSP1)	TTG8HIM	DUS1_HUMAN	Inhibitor	[4]
Indoleamine 2,3-dioxygenase 1 (IDO1)	TTZJYKH	I23O1_HUMAN	Inhibitor	[5]
M-phase inducer phosphatase 2 (MPIP2)	TTR0SWN	MPIP2_HUMAN	Inhibitor	[4]
Plasmodium Dihydroorotate dehydrogenase (Malaria DHOdehase)	TT3PQ2Y	PYRD_PLAF7	Inhibitor	[6]
Rotamase Pin1 (PIN1)	TTJNTSI	PIN1_HUMAN	Inhibitor	[2]
Vascular endothelial growth factor A (VEGFA)	TTOHSBA	VEGFA_HUMAN	Inhibitor	[7]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Apoptosis regulator BAX (BAX)	OTAW0V4V	BAX_HUMAN	Gene/Protein Processing	[8]
Apoptosis regulator Bcl-2 (BCL2)	OT9DVHC0	BCL2_HUMAN	Gene/Protein Processing	[8]
Bcl-2-binding component 3, isoforms 3/4 (BBC3)	OTUAXDAY	BBC3B_HUMAN	Gene/Protein Processing	[8]
Bcl2-associated agonist of cell death (BAD)	OT63ERYM	BAD_HUMAN	Gene/Protein Processing	[8]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Gene/Protein Processing	[8]
Caspase-8 (CASP8)	OTA8TVI8	CASP8_HUMAN	Gene/Protein Processing	[9]
Catenin beta-1 (CTNNB1)	OTZ932A3	CTNB1_HUMAN	Gene/Protein Processing	[8]
Dihydroorotate dehydrogenase (DHODH)	OTAKFN78	PYRD_HUMAN	Gene/Protein Processing	[6]
Disabled homolog 2 (DAB2)	OTRMQTMZ	DAB2_HUMAN	Post-Translational Modifications	[10]
G1/S-specific cyclin-D1 (CCND1)	OT8HPTKJ	CCND1_HUMAN	Gene/Protein Processing	[8]

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Molecular Interaction Atlas (MIA)

MIA Detail

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References

1	Clinical pipeline report, company report or official report of Roche.
2	Overexpression of PIN1 Enhances Cancer Growth and Aggressiveness with Cyclin D1 Induction in EBV-Associated Nasopharyngeal Carcinoma.PLoS One. 2016 Jun 3;11(6):e0156833.
3	Simple analogues of anthralin: unusual specificity of structure and antiproliferative activity. J Med Chem. 1997 Nov 7;40(23):3773-80.
4	Bioactivities of simplified adociaquinone B and naphthoquinone derivatives against Cdc25B, MKP-1, and MKP-3 phosphatases. Bioorg Med Chem. 2009 Mar 15;17(6):2276-81.
5	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.
6	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.
7	Clinical pipeline report, company report or official report of Genentech (2009).
8	Indomethacin and juglone inhibit inflammatory molecules to induce apoptosis in colon cancer cells. J Biochem Mol Toxicol. 2020 Feb;34(2):e22433. doi: 10.1002/jbt.22433. Epub 2020 Jan 9.
9	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.
10	Cell cycle-dependent phosphorylation of Disabled-2 by cdc2. Oncogene. 2003 Jul 17;22(29):4524-30. doi: 10.1038/sj.onc.1206767.