Plumbagin - Compound Card

Plumbagin

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Plumbagin

Structure
Zoomed Structure
  • 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

  • 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
Kegg Ligand: C10387
Chebi: 8273
Nmrshiftdb2: 10116804
Metabolights: MTBLC8273
Drugbank: DB17048
Pdb Ligand: 90R
Bindingdb: 50012070
CPRiL: 54955
Structure

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

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