IMPPAT Phytochemical information: 
[(11R)-14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.01,6.02,13]hexadecan-11-yl] acetate
[(11R)-14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.01,6.02,13]hexadecan-11-yl] acetate
Summary

SMILES: CC(=O)O[C@@H]1CC2C(O)C(CC34C1CCCN4CCCC23)C
InChI: InChI=1S/C18H29NO3/c1-11-10-18-14-5-3-7-19(18)8-4-6-15(18)16(22-12(2)20)9-13(14)17(11)21/h11,13-17,21H,3-10H2,1-2H3/t11?,13?,14?,15?,16-,17?,18?/m1/s1
InChIKey: DQWOXVBLNUYKHM-SPYVFJBBSA-N
DeepSMILES: CC=O)O[C@@H]CCCO)CCCC8CCCN6CCCC%14%10)))))))))))C
Scaffold Graph/Node/Bond level: C1CC2CCC3CCCC24C3CCCN4C1
Scaffold Graph/Node level: C1CC2CCC3CCCC24C3CCCN4C1
Scaffold Graph level: C1CC2CCCC3C4CCCC23C(C1)CC4
Functional groups: CC(=O)OC; CO; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Sesquiterpenoids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids
NP Classifier Class: Quinolizidine alkaloids
Synonymous chemical names:
(-)-fawcettiine
External chemical identifiers:
CID:CID_5317325
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(11R)-14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.01,6.02,13]hexadecan-11-yl] acetate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 307.43
Log P RDKit 2.2
Topological polar surface area (Å2) RDKit 49.77
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.39
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 17
Shape complexity RDKit 0.94
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
[(11R)-14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.01,6.02,13]hexadecan-11-yl] acetate
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 0.754629
[(11R)-14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.01,6.02,13]hexadecan-11-yl] acetate
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 -6.55
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No