IMPPAT Phytochemical information: 
(1S,3S,8S,9R,12S,14R,16S)-16-hydroxy-5,14-dimethyl-5-azatetracyclo[7.7.0.01,12.03,8]hexadecan-10-one
(1S,3S,8S,9R,12S,14R,16S)-16-hydroxy-5,14-dimethyl-5-azatetracyclo[7.7.0.01,12.03,8]hexadecan-10-one
Summary

SMILES: C[C@H]1C[C@H](O)[C@]23[C@@H](C1)CC(=O)[C@@H]3[C@@H]1[C@H](C2)CN(CC1)C
InChI: InChI=1S/C17H27NO2/c1-10-5-12-7-14(19)16-13-3-4-18(2)9-11(13)8-17(12,16)15(20)6-10/h10-13,15-16,20H,3-9H2,1-2H3/t10-,11-,12+,13+,15+,16+,17-/m1/s1
InChIKey: FXQAQYFSGHGITP-QPLXWKHQSA-N
DeepSMILES: C[C@H]C[C@H]O)[C@@][C@@H]C6)CC=O)[C@@H]5[C@@H][C@H]C8)CNCC6))C
Scaffold Graph/Node/Bond level: O=C1CC2CCCCC23CC2CNCCC2C13
Scaffold Graph/Node level: OC1CC2CCCCC23CC2CNCCC2C13
Scaffold Graph level: CC1CC2CCCCC23CC2CCCCC2C13
Functional groups: CN(C)C; CC(=O)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Piperidines
NP Classifier Biosynthetic pathway: Alkaloids|Terpenoids
NP Classifier Superclass: Lysine alkaloids|Pseudoalkaloids
Synonymous chemical names:
paniculatine
External chemical identifiers:
CID:CID_11087072; ZINC:ZINC000038227211
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1S,3S,8S,9R,12S,14R,16S)-16-hydroxy-5,14-dimethyl-5-azatetracyclo[7.7.0.01,12.03,8]hexadecan-10-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 277.41
Log P RDKit 1.94
Topological polar surface area (Å2) RDKit 40.54
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
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 7
Stereochemical complexity RDKit 0.41
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 16
Shape complexity RDKit 0.94
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 1
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 3
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
(1S,3S,8S,9R,12S,14R,16S)-16-hydroxy-5,14-dimethyl-5-azatetracyclo[7.7.0.01,12.03,8]hexadecan-10-one
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 0.735447
(1S,3S,8S,9R,12S,14R,16S)-16-hydroxy-5,14-dimethyl-5-azatetracyclo[7.7.0.01,12.03,8]hexadecan-10-one
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 -6.75
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