IMPPAT Phytochemical information: 
beta-Lapachone
beta-Lapachone
Summary

SMILES: O=C1C2=C(OC(CC2)(C)C)c2c(C1=O)cccc2
InChI: InChI=1S/C15H14O3/c1-15(2)8-7-11-13(17)12(16)9-5-3-4-6-10(9)14(11)18-15/h3-6H,7-8H2,1-2H3
InChIKey: QZPQTZZNNJUOLS-UHFFFAOYSA-N
DeepSMILES: O=CC=COCCC6))C)C)))ccC6=O))cccc6
Scaffold Graph/Node/Bond level: O=C1C(=O)c2ccccc2C2=C1CCCO2
Scaffold Graph/Node level: OC1C(O)C2CCCOC2C2CCCCC12
Scaffold Graph level: CC1C(C)C2CCCCC2C2CCCCC12
Functional groups: COC1=C(C)C(=O)C(=O)cc1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Naphthopyrans
ClassyFire Subclass: Naphthopyranones
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Naphthalenes
NP Classifier Class: Naphthoquinones
Synonymous chemical names:
beta-lapachone, lapachone, beta-, β-lapachone
Covalent inhibitor with Warhead::
CovalentInDB:CI000006 {covintdbwh_formatted};
External chemical identifiers:
CID:3885; ChEMBL:CHEMBL15192; ChEBI:10429; ZINC:ZINC000001531790; FDASRS:6N4FA2QQ6A; SureChEMBL:SCHEMBL107042; MolPort-003-946-081
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
beta-Lapachone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 242.27
Log P RDKit 2.75
Topological polar surface area (Å2) RDKit 43.37
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 0
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 10
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.33
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
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 3
beta-Lapachone
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 0.6569
beta-Lapachone
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.22
Number of PAINS structural alerts SwissADME 2.0
Number of Brenk structural alerts SwissADME 1.0
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
beta-Lapachone
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000293288BAX800
ENSP00000297494NOS3800
ENSP00000319788NQO1861
ENSP00000354522TOP1866
ENSP00000355759PARP1829
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.