IMPPAT Phytochemical information: 
Osthole
Osthole
Summary

SMILES: COc1ccc2c(c1CC=C(C)C)oc(=O)cc2
InChI: InChI=1S/C15H16O3/c1-10(2)4-7-12-13(17-3)8-5-11-6-9-14(16)18-15(11)12/h4-6,8-9H,7H2,1-3H3
InChIKey: MBRLOUHOWLUMFF-UHFFFAOYSA-N
DeepSMILES: COcccccc6CC=CC)C)))))oc=O)cc6
Scaffold Graph/Node/Bond level: O=c1ccc2ccccc2o1
Scaffold Graph/Node level: OC1CCC2CCCCC2O1
Scaffold Graph level: CC1CCC2CCCCC2C1
Functional groups: cOC; CC=C(C)C; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Coumarins and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Simple coumarins
Synonymous chemical names:
osthol, Osthole, Osthol, osthole, ostol
External chemical identifiers:
CID:CID_10228; ChEMBL:CHEMBL52229; ChEBI:CHEBI:69832; ZINC:ZINC000000000566; FDASRS:XH1TI1759C; SureChEMBL:SCHEMBL50436; MolPort-000-881-851
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Osthole
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 244.29
Log P RDKit 3.31
Topological polar surface area (Å2) RDKit 39.44
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 11
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.27
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
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
Osthole
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 0.613912
Osthole
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -5.09
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Osthole
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_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780ChEMBL
TAR_EXP_001106ENSG00000085563ABCB15243ChEMBL, NPASS
TAR_EXP_000556ENSG00000111640GAPDH2597BindingDB, NPASS
TAR_EXP_001299ENSG00000073756PTGS25743BindingDB, ChEMBL, NPASS
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_001679ENSG00000082898XPO17514BindingDB, ChEMBL, NPASS
TAR_EXP_000567ENSG00000177628GBA12629NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000604ENSG00000112164GLP1R2740NPASS
TAR_EXP_001298ENSG00000095303PTGS15742NPASS
TAR_EXP_000491ENSG00000186318BACE123621BindingDB, ChEMBL, NPASS
TAR_EXP_000521ENSG00000022355GABRA12554BindingDB, ChEMBL
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000061ENSG00000134538SLCO1B110599NPASS
TAR_EXP_000102ENSG00000091428RAPGEF411069NPASS
TAR_EXP_000262ENSG00000140465CYP1A11543ChEMBL, NPASS
TAR_EXP_000271ENSG00000165841CYP2C191557ChEMBL, NPASS
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000276ENSG00000272532CYP2D61565ChEMBL, NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_000533ENSG00000113327GABRG22566ChEMBL, NPASS
TAR_EXP_000500ENSG00000275565ALOX5240BindingDB, ChEMBL, NPASS
TAR_EXP_000273ENSG00000138109CYP2C91559ChEMBL, NPASS
TAR_EXP_000528ENSG00000145864GABRB22561ChEMBL