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Plumbagin
- Family: Plantae - Ebenaceae
- Kingdom: Plantae
-
Class: Quinone
- Subclass: Naphthoquinone
Canonical Smiles | CC1=CC(=O)c2c(C1=O)cccc2O |
---|---|
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 |
Formula | C11H8O3 |
HBA | 3 |
HBD | 1 |
MW | 188.18 |
Rotatable Bonds | 0 |
TPSA | 54.37 |
LogP | 1.72 |
Number Rings | 2 |
Number Aromatic Rings | 1 |
Heavy Atom Count | 14 |
Formal Charge | 0 |
Fraction CSP3 | 0.09 |
Exact Mass | 188.05 |
Number of Lipinski Rule Violations | 0 |
# | Species | Family | Kingdom | NCBI Taxonomy ID |
---|---|---|---|---|
1 | Diospyros bipindensis | Ebenaceae | Plantae | 413723 |
2 | Diospyros canaliculata | Ebenaceae | Plantae | 2945278 |
3 | Diospyros crassiflora | Ebenaceae | Plantae | 570480 |
Showing of synonyms
Plumbagin
481-42-5
5-hydroxy-2-methylnaphthalene-1,4-dione
5-Hydroxy-2-methyl-1,4-naphthoquinone
Plumbagine
2-Methyljuglone
Plumbaein
Plumbagone
5-Hydroxy-2-methyl-1,4-naphthalenedione
2-Methyl-5-hydroxy-1,4-naphthoquinone
CCRIS 6671
NSC 236613
NSC 688284
YAS4TBQ4OQ
5-hydroxy-2-methyl-1,4-dihydronaphthalene-1,4-dione
EINECS 207-569-6
NSC-236613
NSC-688284
BRN 1870475
CHEBI:8273
PCUR-101
AI3-38055
PLUMBAGIN [MI]
1,4-NAPHTHOQUINONE, 5-HYDROXY-2-METHYL-
4-08-00-02376 (Beilstein Handbook Reference)
PCUR101
PCUR 101
Synthetic Plumbagin PCUR-101
5-HYDROXY,2-METHYL-1,4-NAPHTOQUINONE
207-569-6
Inchi=1/c11h8o3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12h,1h
1,4-Naphthalenedione, 5-hydroxy-2-methyl-
5-Hydroxy-2-methyl-[1,4]naphthoquinone
MFCD00001682
CHEMBL295316
NSC236613
NSC688284
5-Hydroxy-2-methyl-naphthalene-1,4-dione
SR-05000002263
UNII-YAS4TBQ4OQ
Pumbagin
5-Hydroxy-2-methylnaphthoquinone
Plumbagin (Standard)
Plumbagin [WHO-DD]
ST069355
RTK1
1, 5-hydroxy-2-methyl-
SCHEMBL34186
BSPBio_002546
Plumbagin from Plumbago indica
SPECTRUM1505129
GTPL7003
DTXSID8075413
ACon1_001611
HY-N1497R
HMS3870L13
WLN: L66 BV EVJ C1 GQ
HY-N1497
BDBM50012070
MSK177647
S4777
STL564479
AKOS015969699
CCG-208032
CCG-208410
FP13778
NCGC00094567-01
NCGC00094567-02
NCGC00094567-03
NCGC00094567-04
NCGC00094567-05
NCGC00094567-06
BP-25404
NCI60_001904
PS-11338
DB-051524
CS-0017042
NS00031768
P1139
5- HYDROXY,2-METHYL-1,4-NAPHTOQUINONE
AP-782/41885488
A1-00788
Q2550553
SR-05000002263-2
SR-05000002263-3
BRD-K36137799-001-02-4
BRD-K36137799-001-03-2
Plumbagin2-Methyljuglone
- Lenta NB, Ngamgwe FR, et al. (2015). Compounds from Diospyros canaliculata (Ebenaceae) and their Antiparasitic Activities. Journal of Pure and Applied Chemistry, 2015, 6(2), 56–65. [View]
- Tangmouo J, Meli A, et al. (2006). Crassiflorone, a new naphthoquinone from Diospyros crassiflora (Hien). Tetrahedron Letters, 2006, 47(18), 3067-3070. [View]
- Cesari I, Queiroz EF, et al. (2013). Extensive phytochemical investigation of the polar constituents of Diospyros bipindensis Gürke traditionally used by Baka pygmies.. Phytochemistry,2013, 96, 279-287. [View] [PubMed]
Pubchem:
10205
Cas:
481-42-5
Gnps:
CCMSLIB00004689890
Zinc:
ZINC000000058187
Kegg Ligand:
C10387
Chebi:
8273
Nmrshiftdb2:
10116804
Metabolights:
MTBLC8273
Chembl:
CHEMBL295316
Comptox:
DTXSID8075413
Drugbank:
DB17048
Pdb Ligand:
90R
Bindingdb:
50012070
CPRiL:
54955
SMILES: c1cccc(c12)C(=O)C=CC2=O
Level: 0
Mol. Weight: 188.18 g/mol
Anti-plasmodial
Antibacterial
Absorption
- Caco-2 (logPapp)
- -4.54
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.31
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.77
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.54
- Plasma Protein Binding
- 27.91
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.72
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- 0.67
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.5
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.55
- Micronucleos
- Toxic
- NR-AhR
- Toxic
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 4.64
- Rat (Acute)
- 3.24
- Rat (Chronic Oral)
- 2.7
- Fathead Minnow
- 3.99
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 333.42
- Hydration Free Energy
- -9.3
- Log(D) at pH=7.4
- 1.65
- Log(P)
- 2.64
- Log S
- -3.21
- Log(Vapor Pressure)
- -4.97
- Melting Point
- 127.78
- pKa Acid
- 7.84
- pKa Basic
- 4.49
Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
---|---|---|---|---|---|
Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.9036 |
cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.8816 |
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8450 |
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8396 |
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8232 |
Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8172 |
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8061 |
Chloramphenicol acetyltransferase | P62577 | CAT_ECOLX | Escherichia coli | 2 | 0.7819 |
NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.7776 |
Peptidyl-prolyl cis-trans isomerase FKBP5 | Q13451 | FKBP5_HUMAN | Homo sapiens | 3 | 0.7734 |
Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 2 | 0.7704 |
Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.7612 |
Class 10 plant pathogenesis-related protein 2B | Q9LLQ2 | P102B_LUPLU | Lupinus luteus | 2 | 0.7516 |
Poly [ADP-ribose] polymerase 1 | P09874 | PARP1_HUMAN | Homo sapiens | 3 | 0.7463 |
Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 2 | 0.7412 |
Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7330 |
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7324 |
Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.7316 |
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B | Q13370 | PDE3B_HUMAN | Homo sapiens | 3 | 0.7239 |
17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 2 | 0.7233 |
Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7222 |
Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7186 |
Fatty acid-binding protein, adipocyte | P15090 | FABP4_HUMAN | Homo sapiens | 2 | 0.7171 |
4,4'-diapophytoene synthase | A9JQL9 | CRTM_STAAU | Staphylococcus aureus | 2 | 0.7147 |
Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.7145 |
3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7128 |
Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7111 |
Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7087 |
chitinase | B0Y2Y2 | B0Y2Y2_ASPFC | Aspergillus fumigatus | 3 | 0.7083 |
Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 2 | 0.7079 |
Serine/threonine-protein kinase PLK1 | P53350 | PLK1_HUMAN | Homo sapiens | 3 | 0.7078 |
Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 2 | 0.7045 |
D-alanyl-D-alanine carboxypeptidase | P15555 | DAC_STRSR | Streptomyces sp | 2 | 0.7023 |
Reductase homolog | Q9ZGC1 | Q9ZGC1_STRCY | Streptomyces cyanogenus | 3 | 0.7007 |