IMPPAT Phytochemical information: 
Lapachol
Lapachol
Summary

SMILES: CC(=CCC1=C(O)c2c(C(=O)C1=O)cccc2)C
InChI: InChI=1S/C15H14O3/c1-9(2)7-8-12-13(16)10-5-3-4-6-11(10)14(17)15(12)18/h3-7,16H,8H2,1-2H3
InChIKey: CWPGNVFCJOPXFB-UHFFFAOYSA-N
DeepSMILES: CC=CCC=CO)ccC=O)C6=O)))cccc6))))))))))C
Scaffold Graph/Node/Bond level: O=C1C=Cc2ccccc2C1=O
Scaffold Graph/Node level: OC1CCC2CCCCC2C1O
Scaffold Graph level: CC1CCC2CCCCC2C1C
Functional groups: CC=C(C)C; CC1=C(O)ccC(=O)C1=O
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: Naphthoquinones
Synonymous chemical names:
Tecomin, Lapachol, 2-hydroxy-3(3-methyl-2-butenyl)-1,4-naphthaquinone (lapachol), tecomin, lapachol
External chemical identifiers:
CID:CID_3884; ZINC:ZINC000078934733; SureChEMBL:SCHEMBL157256
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Lapachol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 242.27
Log P RDKit 3.08
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 15
Number of heavy atoms RDKit 18
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 12
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.2
Number of rotatable bonds RDKit 2
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
Lapachol
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 0.640133
Lapachol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
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 -5.80
Number of PAINS structural alerts SwissADME 2
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Lapachol
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_001665ENSG00000111424VDR7421ChEMBL
TAR_EXP_001937ENSG00000101224CDC25B994ChEMBL
TAR_EXP_000626ENSG00000178623GPR352859ChEMBL
TAR_EXP_001663ENSG00000162607USP17398ChEMBL
TAR_EXP_001935ENSG00000164045CDC25A993ChEMBL
TAR_EXP_001547ENSG00000275349SMN16606ChEMBL
TAR_EXP_001431ENSG00000177189RPS6KA36197ChEMBL
TAR_EXP_001128ENSG00000067225PKM5315ChEMBL
TAR_EXP_000853ENSG00000276155MAPT4137ChEMBL
TAR_EXP_001737ENSG00000145391SETD780854ChEMBL
TAR_EXP_000603ENSG00000124767GLO12739ChEMBL
TAR_EXP_000311ENSG00000102967DHODH1723ChEMBL
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL