IMPPAT Phytochemical information: 
(1R,4S,5S,6S,8S,9S)-5,8-dihydroxy-6-methyl-13-azatetracyclo[7.7.0.01,13.04,9]hexadecan-2-one
(1R,4S,5S,6S,8S,9S)-5,8-dihydroxy-6-methyl-13-azatetracyclo[7.7.0.01,13.04,9]hexadecan-2-one
Summary

SMILES: C[C@H]1C[C@H](O)[C@]23[C@@H]([C@H]1O)CC(=O)[C@]13CCCN1CCC2
InChI: InChI=1S/C16H25NO3/c1-10-8-12(18)15-4-2-6-17-7-3-5-16(15,17)13(19)9-11(15)14(10)20/h10-12,14,18,20H,2-9H2,1H3/t10-,11+,12-,14-,15+,16-/m0/s1
InChIKey: XPIVPCYGYLMOCY-KZQACRCDSA-N
DeepSMILES: C[C@H]C[C@H]O)[C@@][C@@H][C@H]6O))CC=O)[C@@]5CCCN5CCC%12
Scaffold Graph/Node/Bond level: O=C1CC2CCCCC23CCCN2CCCC123
Scaffold Graph/Node level: OC1CC2CCCCC23CCCN2CCCC123
Scaffold Graph level: CC1CC2CCCCC23CCCC2CCCC123
Functional groups: CO; CC(=O)C; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Azaspirodecane derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids
NP Classifier Class: Quinolizidine alkaloids
Synonymous chemical names:
serratinine
External chemical identifiers:
CID:CID_11231303; ZINC:ZINC000137337467
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1R,4S,5S,6S,8S,9S)-5,8-dihydroxy-6-methyl-13-azatetracyclo[7.7.0.01,13.04,9]hexadecan-2-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 279.38
Log P RDKit 0.95
Topological polar surface area (Å2) RDKit 60.77
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.38
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.94
Number of rotatable bonds RDKit 0
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
(1R,4S,5S,6S,8S,9S)-5,8-dihydroxy-6-methyl-13-azatetracyclo[7.7.0.01,13.04,9]hexadecan-2-one
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 0.69
(1R,4S,5S,6S,8S,9S)-5,8-dihydroxy-6-methyl-13-azatetracyclo[7.7.0.01,13.04,9]hexadecan-2-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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.50
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 Yes