IMPPAT Phytochemical information: 
Plumbagin
Plumbagin
Summary

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
DeepSMILES: CC=CC=O)ccC6=O))cccc6O
Scaffold Graph/Node/Bond level: O=C1C=CC(=O)c2ccccc21
Scaffold Graph/Node level: OC1CCC(O)C2CCCCC12
Scaffold Graph level: CC1CCC(C)C2CCCCC12
Functional groups: CC1=CC(=O)ccC1=O; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Naphthalenes
ClassyFire Subclass: Naphthoquinones
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Naphthalenes
NP Classifier Class: Naphthalenes and derivatives|Naphthoquinones
Synonymous chemical names:
2-methyl-5-hydroxy-1,4-naphthoquinone (plumbagin), 2-methyl-5-hydroxy-1,4-naphthoquinone(plumbagin), plumbagin, plumbagin(2-methyl-5-hydroxynaphthoquinone), plumbagin(5-hydroxy-2-methyl-1,4-naphthoquinone)
External chemical identifiers:
CID:10205; ChEMBL:CHEMBL295316; ChEBI:8273; ZINC:ZINC000000058187; FDASRS:YAS4TBQ4OQ; SureChEMBL:SCHEMBL34186; MolPort-000-165-362
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Plumbagin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 188.18
Log P RDKit 1.72
Topological polar surface area (Å2) RDKit 54.37
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 11
Number of heavy atoms RDKit 14
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 1
Shape complexity RDKit 0.09
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
Plumbagin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.6739
Plumbagin
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.82
Number of PAINS structural alerts SwissADME 2.0
Number of Brenk structural alerts SwissADME 0.0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Plumbagin
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000215832MAPK1700
ENSP00000219240DHODH800
ENSP00000244741CDKN1A786
ENSP00000254227NR0B2800
ENSP00000263025MAPK3700
ENSP00000270142SOD1826
ENSP00000270202AKT1942
ENSP00000304845UGT1A1700
ENSP00000312436NFE2800
ENSP00000320935SLC2A4800
ENSP00000343838UGT1A10700
ENSP00000346768UGT1A9700
ENSP00000350941SRC800
ENSP00000353483MAPK8850
ENSP00000362525UGT1A7700
ENSP00000362549UGT1A8700
ENSP00000386884CXCR4828
ENSP00000396704TOP2B712
ENSP00000411532TOP2A712
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.