IMPPAT Phytochemical information: 
Piperundecalidine

Piperundecalidine
Summary

SMILES: O=C(N1CCCCC1)/C=C/C=C/CCCC/C=C/c1ccc2c(c1)OCO2
InChI: InChI=1S/C23H29NO3/c25-23(24-16-10-7-11-17-24)13-9-6-4-2-1-3-5-8-12-20-14-15-21-22(18-20)27-19-26-21/h4,6,8-9,12-15,18H,1-3,5,7,10-11,16-17,19H2/b6-4+,12-8+,13-9+
InChIKey: BADLEYLQAILHPV-AZMZBSBOSA-N
DeepSMILES: O=CNCCCCC6))))))/C=C/C=C/CCCC/C=C/cccccc6)OCO5
Scaffold Graph/Node/Bond level: O=C(C=CC=CCCCCC=Cc1ccc2c(c1)OCO2)N1CCCCC1
Scaffold Graph/Node level: OC(CCCCCCCCCCC1CCC2OCOC2C1)N1CCCCC1
Scaffold Graph level: CC(CCCCCCCCCCC1CCC2CCCC2C1)C1CCCCC1
Functional groups: C/C=C/C=C/C(=O)N(C)C; c/C=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:
Piperundecalidine, piperundecalidine
External chemical identifiers:
CID:CID_44453654; ChEMBL:CHEMBL255762; ChEBI:CHEBI:174896; ZINC:ZINC000014658375; MolPort-028-610-080
Chemical structure download


Piperundecalidine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 367.49
Log P RDKit 5.11
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 23
Number of heavy atoms RDKit 27
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 10
Shape complexity RDKit 0.43
Number of rotatable bonds RDKit 8
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


Piperundecalidine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.36


Piperundecalidine
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 -4.44
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No