IMPPAT Phytochemical information: 
Virolane

Virolane
Summary

SMILES: COc1ccc(c(c1)O)CCCc1ccc2c(c1)OCO2
InChI: InChI=1S/C17H18O4/c1-19-14-7-6-13(15(18)10-14)4-2-3-12-5-8-16-17(9-12)21-11-20-16/h5-10,18H,2-4,11H2,1H3
InChIKey: NJMMBJPOBWRSGZ-UHFFFAOYSA-N
DeepSMILES: COcccccc6)O))CCCcccccc6)OCO5
Scaffold Graph/Node/Bond level: c1ccc(CCCc2ccc3c(c2)OCO3)cc1
Scaffold Graph/Node level: C1CCC(CCCC2CCC3OCOC3C2)CC1
Scaffold Graph level: C1CCC(CCCC2CCC3CCCC3C2)CC1
Functional groups: cOC; cO; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenols
ClassyFire Subclass: Methoxyphenols
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
Synonymous chemical names:
virolane
External chemical identifiers:
CID:CID_21722171; ChEMBL:CHEMBL4086047; ZINC:ZINC000013340322
Chemical structure download


Virolane
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 286.33
Log P RDKit 3.3
Topological polar surface area (Å2) RDKit 47.92
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 4
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 12
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.29
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3


Virolane
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 0.92


Virolane
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -5.13
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 Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No