IMPPAT Phytochemical information: 
Cadabicilone

Cadabicilone
Summary

SMILES: CC1C(=O)OC2C1CCC1(C2C(C)C(=O)CC1)C
InChI: InChI=1S/C15H22O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h8-10,12-13H,4-7H2,1-3H3
InChIKey: BXRGGUXPWTWACZ-UHFFFAOYSA-N
DeepSMILES: CCC=O)OCC5CCCC6CC)C=O)CC6)))))C
Scaffold Graph/Node/Bond level: O=C1CCC2CCC3CC(=O)OC3C2C1
Scaffold Graph/Node level: OC1CCC2CCC3CC(O)OC3C2C1
Scaffold Graph level: CC1CCC2CCC3CC(C)CC3C2C1
Functional groups: COC(=O)C; CC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Eudesmane sesquiterpenoids
Synonymous chemical names:
cadabicilone
External chemical identifiers:
CID:CID_325292; ChEMBL:CHEMBL1556978; ChEBI:CHEBI:174307; MolPort-003-724-685
Chemical structure download


Cadabicilone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 250.34
Log P RDKit 2.58
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 6
Stereochemical complexity RDKit 0.4
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 2
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.87
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Cadabicilone
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 0.620571


Cadabicilone
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 -5.92
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No