IMPPAT Phytochemical information: 
Triprolidine

Triprolidine
Summary

SMILES: Cc1ccc(cc1)/C(=C\CN1CCCC1)/c1ccccn1
InChI: InChI=1S/C19H22N2/c1-16-7-9-17(10-8-16)18(19-6-2-3-12-20-19)11-15-21-13-4-5-14-21/h2-3,6-12H,4-5,13-15H2,1H3/b18-11+
InChIKey: CBEQULMOCCWAQT-WOJGMQOQSA-N
DeepSMILES: Ccccccc6))/C=C\CNCCCC5)))))))/cccccn6
Scaffold Graph/Node/Bond level: C(CN1CCCC1)=C(c1ccccc1)c1ccccn1
Scaffold Graph/Node level: C1CCC(C(CCN2CCCC2)C2CCCCN2)CC1
Scaffold Graph level: C1CCC(C(CCC2CCCC2)C2CCCCC2)CC1
Functional groups: c/C(c)=C\C; CN(C)C; cnc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Benzene and substituted derivatives
ClassyFire Subclass: Styrenes
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids
Synonymous chemical names:
3-(but-cis-1-enyl)-pyridine, 3-(but-trans-1-enyl)-pyridine
External chemical identifiers:
CID:CID_5282443; ChEMBL:CHEMBL855; ChEBI:CHEBI:84116; ZINC:ZINC000012503099; FDASRS:2L8T9S52QM; SureChEMBL:SCHEMBL4905; MolPort-003-182-178
Chemical structure download


Triprolidine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 278.4
Log P RDKit 3.92
Topological polar surface area (Å2) RDKit 16.13
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 2
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 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
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


Triprolidine
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 0.84


Triprolidine
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 -5.21
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No