IMPPAT Phytochemical information: 
Ciliaric acid
Ciliaric acid
Summary

SMILES: O[C@@H]1C[C@H]2[C@@]([C@H]3[C@@]41C[C@@H]1[C@](C4)([C@@H]1C3)C)(C)CCC[C@@]2(C)C(=O)O
InChI: InChI=1S/C20H30O3/c1-17-5-4-6-18(2,16(22)23)13(17)8-15(21)20-9-12-11(7-14(17)20)19(12,3)10-20/h11-15,21H,4-10H2,1-3H3,(H,22,23)/t11-,12+,13+,14+,15-,17-,18-,19-,20-/m1/s1
InChIKey: REFPIPGRFRVTDA-UXFRUBCJSA-N
DeepSMILES: O[C@@H]C[C@H][C@@][C@H][C@]6C[C@@H][C@]C5)[C@@H]3C7))C))))))C)CCC[C@@]6C)C=O)O
Scaffold Graph/Node/Bond level: C1CCC2C(C1)CCC13CC4C(CC21)C4C3
Scaffold Graph/Node level: C1CCC2C(C1)CCC13CC4C(CC21)C4C3
Scaffold Graph level: C1CCC2C(C1)CCC13CC4C(CC21)C4C3
Functional groups: CO; CC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Diterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Trachylobane diterpenoids
Synonymous chemical names:
ciliaric, ciliaric acid
External chemical identifiers:
CID:CID_101316716; ZINC:ZINC000238772690
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Ciliaric acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 318.46
Log P RDKit 3.7
Topological polar surface area (Å2) RDKit 57.53
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.45
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 19
Shape complexity RDKit 0.95
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 6
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 6
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Ciliaric acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.77
Ciliaric acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.49
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes