IMPPAT Phytochemical information: 
Candicopimaric acid

Candicopimaric acid
Summary

SMILES: C=C[C@@]1(C)CC[C@H]2C(=C1)CC[C@@H]1[C@]2(C)C[C@@H](C1(C)C)C(=O)O
InChI: InChI=1S/C20H30O2/c1-6-19(4)10-9-14-13(11-19)7-8-16-18(2,3)15(17(21)22)12-20(14,16)5/h6,11,14-16H,1,7-10,12H2,2-5H3,(H,21,22)/t14-,15+,16-,19-,20+/m0/s1
InChIKey: JATONPRVKINGTP-STNJDDFNSA-N
DeepSMILES: C=C[C@@]C)CC[C@H]C=C6)CC[C@@H][C@]6C)C[C@@H]C5C)C))C=O)O
Scaffold Graph/Node/Bond level: C1=C2CCC3CCCC3C2CCC1
Scaffold Graph/Node level: C1CCC2C(C1)CCC1CCCC12
Scaffold Graph level: C1CCC2C(C1)CCC1CCCC12
Functional groups: C=CC; CC(=CC)C; 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: Pimarane and Isopimarane diterpenoids
Synonymous chemical names:
candicopimaric acid
External chemical identifiers:
CID:CID_102090473; ZINC:ZINC000238751357
Chemical structure download


Candicopimaric acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 302.46
Log P RDKit 5.06
Topological polar surface area (Å2) RDKit 37.3
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.75
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 0
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 0
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Candicopimaric acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.72368


Candicopimaric 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 -4.39
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No