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) 0
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
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
CHEMBL8273
CAS Number
481-42-5
UNII
YAS4TBQ4OQ
DrugBank ID
DB17048
TTD ID
D0P0IE
VARIDT ID
DR01476
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

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
Chymotrypsin-like protease CTRL-1 (CTRL) OTB6NA5O CTRL_HUMAN Gene/Protein Processing [3]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [4]
DNA damage-inducible transcript 3 protein (DDIT3) OTI8YKKE DDIT3_HUMAN Gene/Protein Processing [3]
E3 ubiquitin-protein ligase UHRF1 OTBNJUF2 UHRF1_HUMAN Gene/Protein Processing [4]
Metalloproteinase inhibitor 2 (TIMP2) OT8S1RRP TIMP2_HUMAN Gene/Protein Processing [4]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [5]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [5]
Poly polymerase 1 (PARP1) OT310QSG PARP1_HUMAN Gene/Protein Processing [4]
Thioredoxin reductase 1, cytoplasmic OTPY3OKU TRXR1_HUMAN Gene/Protein Processing [5]
Transcription factor E2F1 (E2F1) OTLKYBBC E2F1_HUMAN Gene/Protein Processing [4]
Molecular Interaction Atlas (MIA) 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 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.
4 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.
5 Plumbagin, a novel Nrf2/ARE activator, protects against cerebral ischemia. J Neurochem. 2010 Mar;112(5):1316-26.