Natural Product (NP) Details

General Information of the NP (ID: NP9331)
Name
Plumbagin
Synonyms
Plumbagin; 481-42-5; Plumbagine; 5-Hydroxy-2-methyl-1,4-naphthoquinone; Plumbaein; 5-hydroxy-2-methylnaphthalene-1,4-dione; Plumbagone; 2-Methyljuglone; 1,4-Naphthalenedione, 5-hydroxy-2-methyl-; 5-Hydroxy-2-methyl-[1,4]naphthoquinone; 5-Hydroxy-2-methyl-1,4-naphthalenedione; 2-Methyl-5-hydroxy-1,4-naphthoquinone; UNII-YAS4TBQ4OQ; NSC 236613; NSC 688284; YAS4TBQ4OQ; CHEBI:8273; CHEMBL295316; 1,4-NAPHTHOQUINONE, 5-HYDROXY-2-METHYL-; MFCD00001682; NSC236613; NSC688284; ST069355; 5-Hydroxy-2-methyl-naphthalene-1,4-dione; 5-hydroxy-2-methyl-1,4-dihydronaphthalene-1,4-dione; plumbapin; CCRIS 6671; SR-05000002263; EINECS 207-569-6; BRN 1870475; Ophioxylin; Pumbagin; AI3-38055; Plumbagin, 99+%; RTK1; 1, 5-hydroxy-2-methyl-; SCHEMBL34186; BSPBio_002546; 4-08-00-02376 (Beilstein Handbook Reference); Plumbagin from Plumbago indica; SPECTRUM1505129; GTPL7003; DTXSID8075413; ACon1_001611; ZINC58187; HMS3870L13; WLN: L66 BV EVJ C1 GQ; HY-N1497; ANW-41868; BDBM50012070; s4777; SBB012388; STL564479; AKOS015969699; CCG-208032; CCG-208410; MCULE-9327502882; NSC-236613; NSC-688284; NCGC00094567-01; NCGC00094567-02; NCGC00094567-03; NCGC00094567-04; NCGC00094567-05; NCGC00094567-06; AK-35295; BP-25404; NCI60_001904; PS-11338; 2-methyl-5-oxidanyl-naphthalene-1,4-dione; DB-051524; CS-0017042; FT-0602795; P1139; 5- HYDROXY,2-METHYL-1,4-NAPHTOQUINONE; C10387; K-9170; A827479; 1,4-Naphthalenedione, 5-hydroxy-2-methyl- (9CI); A1-00788; Q2550553; SR-05000002263-2; SR-05000002263-3; W-202844; BRD-K36137799-001-02-4; BRD-K36137799-001-03-2
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Species Origin Plumbago europaea ...     Click to Show/Hide
Plumbago europaea
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Caryophyllales
Family: Plumbaginaceae
Genus: Plumbago
Species: Plumbago europaea
Disease Lung cancer [ICD-11: 2C25] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -4.993
 
MDCK Permeability
 -4.77
 
PAMPA
 ++
 
HIA
 - -
 
Distribution
VDss
 0.044
 
PPB
 97.1%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 +++
CYP1A2 substrate
 +++
CYP2C19 inhibitor
 +++
CYP2C19 substrate
 - - -
CYP2C9 inhibitor
 ++
CYP2C9 substrate
 - - -
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 - - -
CYP3A4 inhibitor
 +++
CYP3A4 substrate
 - - -
CYP2B6 inhibitor
 ++
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 +++
HLM Stability
 ++
 
Excretion
CLplasma
 1.534
 
T1/2
 1.216
Toxicity
DILI
 +++
 
Rat Oral Acute Toxicity
 +
 
FDAMDD
 +++
 
Respiratory
 ++
 
Human Hepatotoxicity
 +
 
Ototoxicity
 - -
 
Drug-induced Nephrotoxicity
 - - -
 
Drug-induced Neurotoxicity
 - - -
 
Hematotoxicity
 - -
 
Genotoxicity
 +++
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C11H8O3
PubChem CID
10205
Canonical SMILES
CC1=CC(=O)C2=C(C1=O)C=CC=C2O
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
CAS Number
CAS 481-42-5
ChEBI ID
CHEBI:8273
Herb ID
HBIN040266
TTD Drug ID
D0P0IE
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Zoledronic      Mineral excesses     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Up-regulation Expression NOTCH1  Molecule Info 
Pathway MAP
                    In-vitro Model MDA-MB-231 CVCL_0062 Breast adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 Combination of Zoledronic acid and Plumbagin synergistically suppresses human breast cancer MDA-MB-231SArfp cells in vitro. Plumbagin can inhibit Zoledronic acid-induced activation of the Notch-1 signaling pathway and subsequently reduce the expression of Bcl-2, thus potentiating cancer cell apoptosis.
          Celecoxib      Rheumatoid arthritis     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression COX-2  Molecule Info 
Pathway MAP
Down-regulation Expression STAT3  Molecule Info 
Pathway MAP
                    In-vitro Model UACC-903 CVCL_4052 Cutaneous melanoma Homo sapiens
Mel JuSo CVCL_1403 Cutaneous melanoma Homo sapiens
A375-M CVCL_B222 Amelanotic melanoma Homo sapiens
1205Lu CVCL_5239 Melanoma Homo sapiens
FF2441 Healthy Homo sapiens
                    In-vivo Model Subcutaneous injection of 1.0 * 106 UACC 903 or 1205 Lu melanoma cells were injected above both the left and right rib cages of 4-5 week-old female Athymic-Foxn1nu nude mice.
                    Experimental
                    Result(s)		 Combination of Celecoxib and Plumbagin decreased melanoma cell proliferation and retarded vascular development of tumors mediated by inhibition of COX-2 and STAT3 leading to decreased levels of key cyclins key on which melanoma cell were dependent for survival.
          Gentamicin      Bacterial infection     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Klebsiella pneumoniae Microorganism model Klebsiella pneumoniae
                    Experimental
                    Result(s)		 Herbal compound plumbagin was identified to stimulate gentamicin uptake by CRKp via enhancing TCA efflux and PMF to achieve a synergistic antibacterial effect. Plumbagin may be used in combination with aminoglycosides for severe CRKp infection by potentiating their therapeutic efficacy and lowering dosage.
Target and Pathway
Target(s) Plasmodium dihydroorotate dehydrogenase (Malaria DHOdehase)  Molecule Info  [5]
KEGG Pathway Pyrimidine metabolism Click to Show/Hide
2 Metabolic pathways
Pathwhiz Pathway Pyrimidine Metabolism Click to Show/Hide
Reactome Pyrimidine biosynthesis Click to Show/Hide
WikiPathways Metabolism of nucleotides Click to Show/Hide
References
Reference 1 Plumbagin engenders apoptosis in lung cancer cells via caspase-9 activation and targeting mitochondrial-mediated ROS induction. Arch Pharm Res. 2020 Feb;43(2):242-256.
Reference 2 Synergistic suppression of human breast cancer cells by combination of plumbagin and zoledronic acid In vitro. Acta Pharmacol Sin. 2015 Sep;36(9):1085-98.
Reference 3 Synergistic inhibitory effects of Celecoxib and Plumbagin on melanoma tumor growth. Cancer Lett. 2017 Jan 28;385:243-250.
Reference 4 Synergistic Effect and Mechanism of Plumbagin with Gentamicin Against Carbapenem-Resistant Klebsiella pneumoniae. Infect Drug Resist. 2020 Aug 7;13:2751-2759.
Reference 5 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.
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