IMPPAT Phytochemical information: 
Encecalin

Encecalin
Summary

SMILES: COc1cc2OC(C)(C)C=Cc2cc1C(=O)C
InChI: InChI=1S/C14H16O3/c1-9(15)11-7-10-5-6-14(2,3)17-12(10)8-13(11)16-4/h5-8H,1-4H3
InChIKey: WXVLCNREBFDEKS-UHFFFAOYSA-N
DeepSMILES: COcccOCC)C)C=Cc6cc%10C=O)C
Scaffold Graph/Node/Bond level: C1=Cc2ccccc2OC1
Scaffold Graph/Node level: C1CCC2OCCCC2C1
Scaffold Graph level: C1CCC2CCCCC2C1
Functional groups: cOC; cC=CC; cC(C)=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 1-benzopyrans
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Meroterpenoids
NP Classifier Class: Merohemiterpenoids
Synonymous chemical names:
Encecaline, encecalin (methyleupatoriochromene), encecaline, encecalin
External chemical identifiers:
CID:CID_114703; ChEMBL:CHEMBL451983; ChEBI:CHEBI:4789; ZINC:ZINC000000897924; SureChEMBL:SCHEMBL4310132; MolPort-001-742-371
Chemical structure download


Encecalin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 232.28
Log P RDKit 3.08
Topological polar surface area (Å2) RDKit 35.53
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 14
Number of heavy atoms RDKit 17
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.36
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


Encecalin
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 0.73


Encecalin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -5.94
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No