IMPPAT Phytochemical information: 
8-ethenyl-5-methylidene-4,4a,6,7,8,8a-hexahydro-3H-naphthalene-2-carboxylic acid

8-ethenyl-5-methylidene-4,4a,6,7,8,8a-hexahydro-3H-naphthalene-2-carboxylic acid
Summary

SMILES: C=CC1CCC(=C)C2C1C=C(CC2)C(=O)O
InChI: InChI=1S/C14H18O2/c1-3-10-5-4-9(2)12-7-6-11(14(15)16)8-13(10)12/h3,8,10,12-13H,1-2,4-7H2,(H,15,16)
InChIKey: OBKSUSLJGNFZDQ-UHFFFAOYSA-N
DeepSMILES: C=CCCCC=C)CC6C=CCC6))C=O)O
Scaffold Graph/Node/Bond level: C=C1CCCC2C=CCCC12
Scaffold Graph/Node level: CC1CCCC2CCCCC12
Scaffold Graph level: CC1CCCC2CCCCC12
Functional groups: C=CC; C=C(C)C; CC=C(C(=O)O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Carboxylic acids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Bicyclogermacrane sesquiterpenoids
Synonymous chemical names:
khusilic acid
External chemical identifiers:
CID:CID_562404
Chemical structure download


8-ethenyl-5-methylidene-4,4a,6,7,8,8a-hexahydro-3H-naphthalene-2-carboxylic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 218.3
Log P RDKit 3.18
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 14
Number of heavy atoms RDKit 16
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 0.21
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.5
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 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
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 2


8-ethenyl-5-methylidene-4,4a,6,7,8,8a-hexahydro-3H-naphthalene-2-carboxylic 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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.722683


8-ethenyl-5-methylidene-4,4a,6,7,8,8a-hexahydro-3H-naphthalene-2-carboxylic 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 -5.54
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