IMPPAT Phytochemical information: 
Apoatropin

Apoatropin
Summary

SMILES: CN1[C@@H]2CC[C@H]1CC(C2)OC(=O)C(=C)c1ccccc1
InChI: InChI=1S/C17H21NO2/c1-12(13-6-4-3-5-7-13)17(19)20-16-10-14-8-9-15(11-16)18(14)2/h3-7,14-16H,1,8-11H2,2H3/t14-,15+,16?
InChIKey: WPUIZWXOSDVQJU-XYPWUTKMSA-N
DeepSMILES: CN[C@@H]CC[C@H]5CCC7)OC=O)C=C)cccccc6
Scaffold Graph/Node/Bond level: C=C(C(=O)OC1CC2CCC(C1)N2)c1ccccc1
Scaffold Graph/Node level: CC(C1CCCCC1)C(O)OC1CC2CCC(C1)N2
Scaffold Graph level: CC(CC1CC2CCC(C2)C1)C(C)C1CCCCC1
Functional groups: CN(C)C; cC(=C)C(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Tropane alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Tropane alkaloids
Synonymous chemical names:
atropamine, apoatropine, apoatropin, apotropine
External chemical identifiers:
CID:CID_12306866; ZINC:ZINC000000000961; SureChEMBL:SCHEMBL24070
Chemical structure download


Apoatropin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 271.36
Log P RDKit 2.87
Topological polar surface area (Å2) RDKit 29.54
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.12
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.47
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 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Apoatropin
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


Apoatropin
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 -5.43
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