IMPPAT Phytochemical information: 
(1S,2R,3R,4S,5S,6S,8S,9S,10R,13S,16S,17R)-8-ethoxy-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-ol
(1S,2R,3R,4S,5S,6S,8S,9S,10R,13S,16S,17R)-8-ethoxy-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-ol
Summary

SMILES: CCO[C@@]12C[C@H](OC)[C@@H]3[C@@H]([C@H]2[C@H]([C@@]24[C@H]5[C@@H]1C[C@@H]2[C@@](CN5CC)(COC)CC[C@@H]4OC)C3)O
InChI: InChI=1S/C26H43NO5/c1-6-27-13-24(14-29-3)9-8-20(31-5)26-16-10-15-18(30-4)12-25(32-7-2,21(16)22(15)28)17(23(26)27)11-19(24)26/h15-23,28H,6-14H2,1-5H3/t15-,16-,17+,18+,19-,20+,21-,22+,23-,24+,25+,26-/m1/s1
InChIKey: HVTHYGUXWWSVGZ-LTPKDCRKSA-N
DeepSMILES: CCO[C@]C[C@H]OC))[C@@H][C@@H][C@H]6[C@H][C@@][C@H][C@@H]%10C[C@@H]5[C@@]CN7CC))))COC)))CC[C@@H]9OC)))))))))))C5)))O
Scaffold Graph/Node/Bond level: C1CC2CNC3C4CC2C3(C1)C1CC2CCC4C1C2
Scaffold Graph/Node level: C1CC2CNC3C4CC2C3(C1)C1CC2CCC4C1C2
Scaffold Graph level: C1CC2CCC3C4CC2C3(C1)C1CC2CCC4C1C2
Functional groups: COC; CN(C)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Diterpenoids
NP Classifier Biosynthetic pathway: Alkaloids|Terpenoids
NP Classifier Superclass: Pseudoalkaloids
NP Classifier Class: Terpenoid alkaloids
Synonymous chemical names:
columbidine
External chemical identifiers:
CID:CID_101995817; ZINC:ZINC000255218845
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1S,2R,3R,4S,5S,6S,8S,9S,10R,13S,16S,17R)-8-ethoxy-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-ol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 449.63
Log P RDKit 2.58
Topological polar surface area (Å2) RDKit 60.39
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 12
Stereochemical complexity RDKit 0.46
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 0
Number of sp3 hybridized carbon atoms RDKit 26
Shape complexity RDKit 1
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 5
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
(1S,2R,3R,4S,5S,6S,8S,9S,10R,13S,16S,17R)-8-ethoxy-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-ol
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 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.644753
(1S,2R,3R,4S,5S,6S,8S,9S,10R,13S,16S,17R)-8-ethoxy-11-ethyl-6,16-dimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-ol
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 -7.75
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 Yes