IMPPAT Phytochemical information: 
3-[(E)-(1,3-Benzodioxole-5-yl)methylene]-4-piperonyltetrahydrofuran-2-one
3-[(E)-(1,3-Benzodioxole-5-yl)methylene]-4-piperonyltetrahydrofuran-2-one
Summary

SMILES: O=C1OCC(/C/1=C\c1ccc2c(c1)OCO2)Cc1ccc2c(c1)OCO2
InChI: InChI=1S/C20H16O6/c21-20-15(6-13-2-4-17-19(8-13)26-11-24-17)14(9-22-20)5-12-1-3-16-18(7-12)25-10-23-16/h1-4,6-8,14H,5,9-11H2/b15-6+
InChIKey: CMJGAYUQSLJSCR-GIDUJCDVSA-N
DeepSMILES: O=COCC/C/5=C\cccccc6)OCO5))))))))))Ccccccc6)OCO5
Scaffold Graph/Node/Bond level: O=C1OCC(Cc2ccc3c(c2)OCO3)C1=Cc1ccc2c(c1)OCO2
Scaffold Graph/Node level: OC1OCC(CC2CCC3OCOC3C2)C1CC1CCC2OCOC2C1
Scaffold Graph level: CC1CCC(CC2CCC3CCCC3C2)C1CC1CCC2CCCC2C1
Functional groups: c/C=C1\CCOC1=O; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Furanoid lignans
ClassyFire Subclass: Tetrahydrofuran lignans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Dibenzylbutyrolactone lignans
Synonymous chemical names:
(-)savinin
External chemical identifiers:
CID:CID_5321147
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
3-[(E)-(1,3-Benzodioxole-5-yl)methylene]-4-piperonyltetrahydrofuran-2-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 352.34
Log P RDKit 2.94
Topological polar surface area (Å2) RDKit 63.22
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.25
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
3-[(E)-(1,3-Benzodioxole-5-yl)methylene]-4-piperonyltetrahydrofuran-2-one
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 0.625162
3-[(E)-(1,3-Benzodioxole-5-yl)methylene]-4-piperonyltetrahydrofuran-2-one
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 -5.88
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No