Details of the Drug

General Information of Drug (ID: DM9BS50)

Drug Name

Plumbagin

Synonyms

Plumbagin; 481-42-5; Plumbagine; 5-Hydroxy-2-methyl-1,4-naphthoquinone; Plumbaein; Plumbagone; 2-Methyljuglone; 5-hydroxy-2-methylnaphthalene-1,4-dione; 5-Hydroxy-2-methyl-1,4-naphthalenedione; 5-Hydroxy-2-methyl-[1,4]naphthoquinone; 1,4-Naphthalenedione, 5-hydroxy-2-methyl-; 2-Methyl-5-hydroxy-1,4-naphthoquinone; UNII-YAS4TBQ4OQ; NSC 688284; NSC 236613; CCRIS 6671; YAS4TBQ4OQ; EINECS 207-569-6; BRN 1870475; AI3-38055; CHEBI:8273; CHEMBL295316; VCMMXZQDRFWYSE-UHFFFAOYSA-N; 1,4-NAPHTHOQUINONE, 5-HYDROXY-2-METHYL-; NSC688284

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)

188.18

Logarithm of the Partition Coefficient (xlogp)

2.3

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C11H8O3
IUPAC Name: 5-hydroxy-2-methylnaphthalene-1,4-dione
Canonical SMILES: CC1=CC(=O)C2=C(C1=O)C=CC=C2O
InChI: InChI=1S/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3
InChIKey: VCMMXZQDRFWYSE-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 10205
ChEBI ID: CHEBI:8273
CAS Number: 481-42-5
UNII: YAS4TBQ4OQ
DrugBank ID: DB17048
TTD ID: D0P0IE
VARIDT ID: DR01476

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Plasmodium Dihydroorotate dehydrogenase (Malaria DHOdehase)	TT3PQ2Y	PYRD_PLAF7	Inhibitor	[2]

------------------------------------------------------------------------------------

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
72 kDa type IV collagenase (MMP2)	OT5NIWA2	MMP2_HUMAN	Gene/Protein Processing	[3]
Caspase-9 (CASP9)	OTD4RFFG	CASP9_HUMAN	Gene/Protein Processing	[3]
Chymotrypsin-like protease CTRL-1 (CTRL)	OTB6NA5O	CTRL_HUMAN	Gene/Protein Processing	[4]
Cyclin-dependent kinase inhibitor 1 (CDKN1A)	OTQWHCZE	CDN1A_HUMAN	Gene/Protein Processing	[3]
Dihydroorotate dehydrogenase (DHODH)	OTAKFN78	PYRD_HUMAN	Gene/Protein Processing	[2]
DNA damage-inducible transcript 3 protein (DDIT3)	OTI8YKKE	DDIT3_HUMAN	Gene/Protein Processing	[4]
E3 ubiquitin-protein ligase UHRF1	OTBNJUF2	UHRF1_HUMAN	Gene/Protein Processing	[3]
Endoplasmic reticulum chaperone BiP (HSPA5)	OTFUIRAO	BIP_HUMAN	Gene/Protein Processing	[4]
Glutamate--cysteine ligase regulatory subunit (GCLM)	OT6CP234	GSH0_HUMAN	Gene/Protein Processing	[5]
Glutathione S-transferase P (GSTP1)	OTLP0A0Y	GSTP1_HUMAN	Gene/Protein Processing	[5]

------------------------------------------------------------------------------------

Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7003).
2	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.
3	Plumbagin downregulates UHRF1, p-Akt, MMP-2 and suppresses survival, growth and migration of cervical cancer CaSki cells. Toxicol In Vitro. 2023 Feb;86:105512. doi: 10.1016/j.tiv.2022.105512. Epub 2022 Nov 4.
4	Plumbagin induces paraptosis in cancer cells by disrupting the sulfhydryl homeostasis and proteasomal function. Chem Biol Interact. 2019 Sep 1;310:108733. doi: 10.1016/j.cbi.2019.108733. Epub 2019 Jul 2.
5	Plumbagin, a novel Nrf2/ARE activator, protects against cerebral ischemia. J Neurochem. 2010 Mar;112(5):1316-26.