IMPPAT Phytochemical information: 
Pisiferic acid

Pisiferic acid
Summary

SMILES: OC(=O)[C@@]12CCCC([C@@H]2CCc2c1cc(O)c(c2)C(C)C)(C)C
InChI: InChI=1S/C20H28O3/c1-12(2)14-10-13-6-7-17-19(3,4)8-5-9-20(17,18(22)23)15(13)11-16(14)21/h10-12,17,21H,5-9H2,1-4H3,(H,22,23)/t17-,20-/m0/s1
InChIKey: ATHWSPHADLLZSS-PXNSSMCTSA-N
DeepSMILES: OC=O)[C@]CCCC[C@@H]6CCcc%10ccO)cc6)CC)C))))))))))C)C
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CCC1CCCCC21
Scaffold Graph/Node level: C1CCC2C(C1)CCC1CCCCC12
Scaffold Graph level: C1CCC2C(C1)CCC1CCCCC12
Functional groups: CC(=O)O; cO
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: Abietane diterpenoids
Synonymous chemical names:
pisiferic acid
External chemical identifiers:
CID:CID_162209; ChEBI:CHEBI:70576; ZINC:ZINC000004097932; SureChEMBL:SCHEMBL1439596
Chemical structure download


Pisiferic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 316.44
Log P RDKit 4.61
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 2
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.65
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 0
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 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Pisiferic acid
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.837356


Pisiferic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Moderately 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 -4.50
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 No