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:
Lapachone, beta-, beta-lapachone, lapachone, beta-, β-lapachone
External chemical identifiers:
CID:CID_3885; ChEMBL:CHEMBL15192; ChEBI: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
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 0.656892
beta-Lapachone
ADME 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
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_000271ENSG00000165841CYP2C191557ChEMBL, NPASS
TAR_EXP_000833ENSG00000160789LMNA4000NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245BindingDB, ChEMBL, NPASS
TAR_EXP_000846ENSG00000100299ARSA410NPASS
TAR_EXP_000845ENSG00000166949SMAD34088ChEMBL, NPASS
TAR_EXP_000860ENSG00000152601MBNL14154ChEMBL, NPASS
TAR_EXP_000818ENSG00000187258NPSR1387129NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_000881ENSG00000087085ACHE43ChEMBL, NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780NPASS
TAR_EXP_000968ENSG00000109320NFKB14790ChEMBL, NPASS
TAR_EXP_000853ENSG00000276155MAPT4137ChEMBL, NPASS
TAR_EXP_000798ENSG00000055118KCNH23757NPASS
TAR_EXP_000766ENSG00000131203IDO13620BindingDB, ChEMBL, NPASS
TAR_EXP_000752ENSG00000142192APP351NPASS
TAR_EXP_000273ENSG00000138109CYP2C91559ChEMBL, NPASS
TAR_EXP_000276ENSG00000272532CYP2D61565ChEMBL, NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000119ENSG00000101751POLI11201ChEMBL, NPASS
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000095ENSG00000224143EHMT210919ChEMBL, NPASS
TAR_EXP_000093ENSG00000172175MALT110892ChEMBL, NPASS
TAR_EXP_000065ENSG00000198848CES11066ChEMBL, NPASS
TAR_EXP_000312ENSG00000181019NQO11728BindingDB, ChEMBL, NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000263ENSG00000140505CYP1A21544ChEMBL, NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_000433ENSG00000168496FEN12237NPASS
TAR_EXP_000503ENSG00000161905ALOX15246NPASS
TAR_EXP_000504ENSG00000179593ALOX15B247NPASS
TAR_EXP_000505ENSG00000198793MTOR2475NPASS
TAR_EXP_000545ENSG00000108479GALK12584ChEMBL, NPASS
TAR_EXP_000593ENSG00000102393GLA2717NPASS
TAR_EXP_000687ENSG00000100644HIF1A3091NPASS
TAR_EXP_000715ENSG00000044574HSPA53309NPASS
TAR_EXP_000724ENSG00000144381HSPD13329ChEMBL, NPASS
TAR_EXP_000725ENSG00000115541HSPE13336ChEMBL, NPASS
TAR_EXP_000413ENSG00000117480FAAH2166ChEMBL, NPASS
TAR_EXP_000324ENSG00000184845DRD11812NPASS
TAR_EXP_001153ENSG00000127948POR5447BindingDB, ChEMBL, NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_000969ENSG00000077150NFKB24791ChEMBL
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_001230ENSG00000100030MAPK15594NPASS
TAR_EXP_001360ENSG00000004700RECQL5965ChEMBL, NPASS
TAR_EXP_001362ENSG00000173039RELA5970ChEMBL, NPASS
TAR_EXP_001366ENSG00000117152RGS45999ChEMBL, NPASS
TAR_EXP_001468ENSG00000204842ATXN26311ChEMBL, NPASS
TAR_EXP_001485ENSG00000197299BLM641ChEMBL, NPASS
TAR_EXP_001547ENSG00000275349SMN16606NPASS
TAR_EXP_001605ENSG00000198959TGM27052BindingDB
TAR_EXP_001607ENSG00000090534THPO7066ChEMBL, NPASS
TAR_EXP_001609ENSG00000151090THRB7068NPASS
TAR_EXP_001621ENSG00000141510TP537157ChEMBL, NPASS
TAR_EXP_001633ENSG00000128311TST7263ChEMBL, NPASS
TAR_EXP_001551ENSG00000145335SNCA6622NPASS
TAR_EXP_001665ENSG00000111424VDR7421ChEMBL, NPASS
TAR_EXP_001076ENSG00000111802TDP251567BindingDB, ChEMBL, NPASS
TAR_EXP_001663ENSG00000162607USP17398ChEMBL, NPASS
TAR_EXP_001141ENSG00000109099PMP225376NPASS
TAR_EXP_001151ENSG00000170734POLH5429ChEMBL, NPASS
TAR_EXP_001900ENSG00000123595RAB9A9367NPASS
TAR_EXP_001125ENSG00000127445PIN15300NPASS
TAR_EXP_001173ENSG00000196199MPHOSPH854737NPASS
TAR_EXP_001810ENSG00000067955CBFB865NPASS
TAR_EXP_001753ENSG00000137752CASP1834BindingDB
TAR_EXP_001828ENSG00000172831CES28824BindingDB, ChEMBL, NPASS
TAR_EXP_001728ENSG00000176208ATAD579915NPASS