IMPPAT Phytochemical information: 
Pleiocarpamine

Pleiocarpamine
Summary

SMILES: COC(=O)[C@@H]1[C@H]2C[C@H]3c4n1c1ccccc1c4CCN3C/C/2=C/C
InChI: InChI=1S/C20H22N2O2/c1-3-12-11-21-9-8-14-13-6-4-5-7-16(13)22-18(14)17(21)10-15(12)19(22)20(23)24-2/h3-7,15,17,19H,8-11H2,1-2H3/b12-3-/t15-,17-,19-/m0/s1
InChIKey: NTMOAQDHNZYZMZ-QWCNWJGKSA-N
DeepSMILES: COC=O)[C@@H][C@H]C[C@H]cn6cccccc6c9CCN%13C/C/%17=C/C
Scaffold Graph/Node/Bond level: C=C1CN2CCc3c4n(c5ccccc35)CC1CC42
Scaffold Graph/Node level: CC1CN2CCC3C4CCCCC4N4CC1CC2C34
Scaffold Graph level: CC1CC2CCC3C4CCCCC4C4CC1CC2C34
Functional groups: COC(C)=O; cn(c)C; CN(C)C; C/C=C(/C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Pleiocarpaman alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
pleiocarpamine, Pleiocarpamine
External chemical identifiers:
CID:CID_5385014; ChEMBL:CHEMBL3338254; ChEBI:CHEBI:141939
Chemical structure download


Pleiocarpamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 322.41
Log P RDKit 3.23
Topological polar surface area (Å2) RDKit 34.47
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.45
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
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


Pleiocarpamine
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 0.6


Pleiocarpamine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.53
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No