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

SMILES: CO[C@H]1C[C@@]2(O)[C@H]3[C@H]([C@@H]1C[C@H]3[C@@]13C4[C@@H]2C[C@@H]1[C@H](CN4CC)CC[C@@H]3OC)O
InChI: InChI=1S/C22H35NO4/c1-4-23-10-11-5-6-17(27-3)22-13(11)8-15(20(22)23)21(25)9-16(26-2)12-7-14(22)18(21)19(12)24/h11-20,24-25H,4-10H2,1-3H3/t11-,12+,13+,14+,15-,16-,17-,18+,19-,20?,21-,22-/m0/s1
InChIKey: VCOQRRVEIUTMFC-XSRLUBOPSA-N
DeepSMILES: CO[C@H]C[C@@]O)[C@H][C@H][C@@H]6C[C@H]5[C@@]C[C@@H]9C[C@@H]5[C@H]CN7CC))))CC[C@@H]9OC))))))))))))))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; CO; CN(C)C
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:
aconosine
External chemical identifiers:
CID:CID_21572757; SureChEMBL:SCHEMBL9012319
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1R,2R,3R,4S,5S,6S,8S,9S,13R,16S,17R)-11-ethyl-6,16-dimethoxy-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecane-4,8-diol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 377.53
Log P RDKit 1.51
Topological polar surface area (Å2) RDKit 62.16
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 12
Stereochemical complexity RDKit 0.55
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 0
Number of sp3 hybridized carbon atoms RDKit 22
Shape complexity RDKit 1
Number of rotatable bonds RDKit 3
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
(1R,2R,3R,4S,5S,6S,8S,9S,13R,16S,17R)-11-ethyl-6,16-dimethoxy-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecane-4,8-diol
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 0.78
(1R,2R,3R,4S,5S,6S,8S,9S,13R,16S,17R)-11-ethyl-6,16-dimethoxy-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecane-4,8-diol
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