IMPPAT Phytochemical information: 
[(1S,3S,5R,6S)-8-methyl-6-[(E)-2-methylbut-2-enoyl]oxy-8-azabicyclo[3.2.1]octan-3-yl] (E)-2-methylbut-2-enoate
[(1S,3S,5R,6S)-8-methyl-6-[(E)-2-methylbut-2-enoyl]oxy-8-azabicyclo[3.2.1]octan-3-yl] (E)-2-methylbut-2-enoate
Summary

SMILES: C/C=C(/C(=O)O[C@H]1C[C@H]2C[C@@H]([C@@H](C1)N2C)OC(=O)/C(=C/C)/C)\C
InChI: InChI=1S/C18H27NO4/c1-6-11(3)17(20)22-14-8-13-9-16(15(10-14)19(13)5)23-18(21)12(4)7-2/h6-7,13-16H,8-10H2,1-5H3/b11-6+,12-7+/t13-,14-,15+,16-/m0/s1
InChIKey: MJJVORBCNQQRMU-AVNBRKTCSA-N
DeepSMILES: C/C=C/C=O)O[C@H]C[C@H]C[C@@H][C@@H]C7)N5C)))OC=O)/C=C/C))/C)))))))))))\C
Scaffold Graph/Node/Bond level: C1CC2CCC(C1)N2
Scaffold Graph/Node level: C1CC2CCC(C1)N2
Scaffold Graph level: C1CC2CCC(C1)C2
Functional groups: C/C=C(\C)C(=O)OC; CN(C)C
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:
(-)-3alpha,6beta-ditigloyloxytropane, 3alpha-6beta-ditigloyloxytropane, 3alpha,6beta-ditigloyloxytropane, 3α,6β-ditigloyloxytropane
External chemical identifiers:
CID:CID_21159049; ZINC:ZINC000033830854; SureChEMBL:SCHEMBL19409971
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(1S,3S,5R,6S)-8-methyl-6-[(E)-2-methylbut-2-enoyl]oxy-8-azabicyclo[3.2.1]octan-3-yl] (E)-2-methylbut-2-enoate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 321.42
Log P RDKit 2.61
Topological polar surface area (Å2) RDKit 55.84
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.22
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.67
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
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 2
[(1S,3S,5R,6S)-8-methyl-6-[(E)-2-methylbut-2-enoyl]oxy-8-azabicyclo[3.2.1]octan-3-yl] (E)-2-methylbut-2-enoate
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.588333
[(1S,3S,5R,6S)-8-methyl-6-[(E)-2-methylbut-2-enoyl]oxy-8-azabicyclo[3.2.1]octan-3-yl] (E)-2-methylbut-2-enoate
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 -5.90
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No