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), Plumbagin, plumbagin, plumbagin(2-methyl-5-hydroxynaphthoquinone), plumbagin(5-hydroxy-2-methyl-1,4-naphthoquinone), 2-methyl-5-hydroxy-1,4-naphthoquinone(plumbagin)
External chemical identifiers:
CID:CID_10205; ChEMBL:CHEMBL295316; ChEBI: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
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 0.673931
Plumbagin
ADME 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
Number of Brenk structural alerts SwissADME 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
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_001621ENSG00000141510TP537157ChEMBL, NPASS
TAR_EXP_001937ENSG00000101224CDC25B994BindingDB, ChEMBL, NPASS
TAR_EXP_001679ENSG00000082898XPO17514ChEMBL
TAR_EXP_001633ENSG00000128311TST7263ChEMBL, NPASS
TAR_EXP_001663ENSG00000162607USP17398ChEMBL, NPASS
TAR_EXP_001665ENSG00000111424VDR7421ChEMBL, NPASS
TAR_EXP_001860ENSG00000006062MAP3K149020ChEMBL, NPASS
TAR_EXP_001857ENSG00000104321TRPA18989ChEMBL, NPASS
TAR_EXP_001833ENSG00000114166KAT2B8850BindingDB, ChEMBL, NPASS
TAR_EXP_001764ENSG00000165806CASP7840NPASS
TAR_EXP_001753ENSG00000137752CASP1834NPASS
TAR_EXP_001935ENSG00000164045CDC25A993BindingDB, ChEMBL, NPASS
TAR_EXP_001618ENSG00000198900TOP17150ChEMBL, NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_001547ENSG00000275349SMN16606NPASS
TAR_EXP_000263ENSG00000140505CYP1A21544ChEMBL, NPASS
TAR_EXP_000264ENSG00000138061CYP1B11545ChEMBL, NPASS
TAR_EXP_000271ENSG00000165841CYP2C191557ChEMBL, NPASS
TAR_EXP_000273ENSG00000138109CYP2C91559ChEMBL, NPASS
TAR_EXP_000276ENSG00000272532CYP2D61565ChEMBL, NPASS
TAR_EXP_000348ENSG00000146648EGFR1956ChEMBL
TAR_EXP_000369ENSG00000100393EP3002033BindingDB, ChEMBL, NPASS
TAR_EXP_000387ENSG00000141736ERBB22064ChEMBL, NPASS
TAR_EXP_000390ENSG00000142208AKT1207ChEMBL
TAR_EXP_000411ENSG00000165092ALDH1A1216ChEMBL, NPASS
TAR_EXP_000503ENSG00000161905ALOX15246NPASS
TAR_EXP_000572ENSG00000108773KAT2A2648NPASS
TAR_EXP_000676ENSG00000072506HSD17B103028ChEMBL, NPASS
TAR_EXP_000701ENSG00000164120HPGD3248ChEMBL, NPASS
TAR_EXP_000706ENSG00000291796APEX1328NPASS
TAR_EXP_000715ENSG00000044574HSPA53309NPASS
TAR_EXP_000724ENSG00000144381HSPD13329ChEMBL, NPASS
TAR_EXP_001485ENSG00000197299BLM641NPASS
TAR_EXP_001362ENSG00000173039RELA5970ChEMBL
TAR_EXP_001360ENSG00000004700RECQL5965NPASS
TAR_EXP_001342ENSG00000132155RAF15894NPASS
TAR_EXP_001301ENSG00000169398PTK25747ChEMBL
TAR_EXP_001245ENSG00000076984MAP2K75609ChEMBL, NPASS
TAR_EXP_001568ENSG00000168610STAT36774ChEMBL, NPASS
TAR_EXP_001240ENSG00000169032MAP2K15604NPASS
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_001059ENSG00000122008POLK51426ChEMBL, NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_000853ENSG00000276155MAPT4137ChEMBL, NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245ChEMBL, NPASS
TAR_EXP_000725ENSG00000115541HSPE13336ChEMBL, NPASS
TAR_EXP_001231ENSG00000102882MAPK35595ChEMBL
TAR_EXP_000262ENSG00000140465CYP1A11543ChEMBL, NPASS
TAR_EXP_001230ENSG00000100030MAPK15594ChEMBL, NPASS