IMPPAT Phytochemical information: 
Isokhusenic acid

Isokhusenic acid
Summary

SMILES: OC(=O)[C@H]1CCC2=C(C([C@H]3C[C@@]12CC3)(C)C)C
InChI: InChI=1S/C15H22O2/c1-9-11-4-5-12(13(16)17)15(11)7-6-10(8-15)14(9,2)3/h10,12H,4-8H2,1-3H3,(H,16,17)/t10-,12-,15-/m1/s1
InChIKey: DHPMFKAJSXGYDJ-IXPVHAAZSA-N
DeepSMILES: OC=O)[C@H]CCC=CC[C@H]C[C@@]96CC5)))))C)C))C
Scaffold Graph/Node/Bond level: C1=C2CCCC23CCC(C1)C3
Scaffold Graph/Node level: C1CC2CCC3CCC2(C1)C3
Scaffold Graph level: C1CC2CCC3CCC2(C1)C3
Functional groups: CC(=O)O; CC(C)=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Sesquiterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Zizaane sesquiterpenoids
Synonymous chemical names:
isokhusenic acid, Isokhusenic acid
External chemical identifiers:
CID:CID_12304515
Chemical structure download


Isokhusenic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 234.34
Log P RDKit 3.62
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 15
Number of heavy atoms RDKit 17
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.2
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.8
Number of rotatable bonds RDKit 1
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


Isokhusenic 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 0.7


Isokhusenic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
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 -5.53
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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