IMPPAT Phytochemical information: 
[(1S,2R,3R,4R,5R,6S,7S,8R,10R,13R,14R,16S,17S,18R)-11-ethyl-5,7,8,14-tetrahydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate
[(1S,2R,3R,4R,5R,6S,7S,8R,10R,13R,14R,16S,17S,18R)-11-ethyl-5,7,8,14-tetrahydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate
Summary

SMILES: COC[C@@]12CN(CC)[C@H]3[C@]4([C@@H]2C(OC)C3[C@@]2([C@@H]3[C@H]4C[C@@]([C@@H]3OC(=O)c3ccccc3)([C@H]([C@@H]2O)OC)O)O)[C@H](C[C@H]1O)OC
InChI: InChI=1S/C32H45NO10/c1-6-33-14-29(15-39-2)18(34)12-19(40-3)31-17-13-30(37)26(43-28(36)16-10-8-7-9-11-16)20(17)32(38,25(35)27(30)42-5)21(24(31)33)22(41-4)23(29)31/h7-11,17-27,34-35,37-38H,6,12-15H2,1-5H3/t17-,18-,19+,20-,21?,22?,23-,24-,25+,26-,27+,29+,30-,31+,32-/m1/s1
InChIKey: DHJXZSFKLJCHLH-AGZZDVASSA-N
DeepSMILES: COC[C@]CNCC))[C@H][C@][C@@H]6COC))C5[C@@][C@@H][C@H]7C[C@@][C@@H]5OC=O)cccccc6)))))))))[C@H][C@@H]7O))OC)))O)))))O)))))[C@H]C[C@H]8O)))OC
Scaffold Graph/Node/Bond level: O=C(OC1C2CCC3C4CC5C6CCCC5(C(C2)C31)C4NC6)c1ccccc1
Scaffold Graph/Node level: OC(OC1C2CCC3C4CC5C6CCCC5(C(C2)C31)C4NC6)C1CCCCC1
Scaffold Graph level: CC(CC1C2CCC3C4CC5C6CCCC5(C4CC6)C(C2)C13)C1CCCCC1
Functional groups: CO; COC; CN(C)C; cC(=O)OC
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:
benzaconine, benzoylaconine
External chemical identifiers:
CID:CID_102004487; MolPort-039-052-348
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(1S,2R,3R,4R,5R,6S,7S,8R,10R,13R,14R,16S,17S,18R)-11-ethyl-5,7,8,14-tetrahydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 603.71
Log P RDKit 0.08
Topological polar surface area (Å2) RDKit 147.38
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 32
Number of heavy atoms RDKit 43
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 15
Stereochemical complexity RDKit 0.47
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 25
Shape complexity RDKit 0.78
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 7
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 7
[(1S,2R,3R,4R,5R,6S,7S,8R,10R,13R,14R,16S,17S,18R)-11-ethyl-5,7,8,14-tetrahydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.299643
[(1S,2R,3R,4R,5R,6S,7S,8R,10R,13R,14R,16S,17S,18R)-11-ethyl-5,7,8,14-tetrahydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.20
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