IMPPAT Phytochemical information: 
(2E,4E,6E)-7-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)hepta-2,4,6-trien-1-one

(2E,4E,6E)-7-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)hepta-2,4,6-trien-1-one
Summary

SMILES: O=C(N1CCCCC1)/C=C/C=C/C=C/c1ccc2c(c1)OCO2
InChI: InChI=1S/C19H21NO3/c21-19(20-12-6-3-7-13-20)9-5-2-1-4-8-16-10-11-17-18(14-16)23-15-22-17/h1-2,4-5,8-11,14H,3,6-7,12-13,15H2/b2-1+,8-4+,9-5+
InChIKey: DLKOUKNODPCIHZ-UMYWTXKFSA-N
DeepSMILES: O=CNCCCCC6))))))/C=C/C=C/C=C/cccccc6)OCO5
Scaffold Graph/Node/Bond level: O=C(C=CC=CC=Cc1ccc2c(c1)OCO2)N1CCCCC1
Scaffold Graph/Node level: OC(CCCCCCC1CCC2OCOC2C1)N1CCCCC1
Scaffold Graph level: CC(CCCCCCC1CCC2CCCC2C1)C1CCCCC1
Functional groups: c/C=C/C=C/C=C/C(=O)N(C)C; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzodioxoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids
NP Classifier Class: Piperidine alkaloids
Synonymous chemical names:
piperettine, Piperettine
External chemical identifiers:
CID:CID_10244953; ChEMBL:CHEMBL324315; ZINC:ZINC000014657880; SureChEMBL:SCHEMBL14200750
Chemical structure download


(2E,4E,6E)-7-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)hepta-2,4,6-trien-1-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 311.38
Log P RDKit 3.55
Topological polar surface area (Å2) RDKit 38.77
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 1
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 13
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.32
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
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 3


(2E,4E,6E)-7-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)hepta-2,4,6-trien-1-one
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 0.63


(2E,4E,6E)-7-(2H-1,3-benzodioxol-5-yl)-1-(piperidin-1-yl)hepta-2,4,6-trien-1-one
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.28
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No