IMPPAT Phytochemical information: 
[(1S,2R,3R,4R,5S,6S,8R,9R,10R,13S,16S,17R,18R)-8-acetyloxy-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate
[(1S,2R,3R,4R,5S,6S,8R,9R,10R,13S,16S,17R,18R)-8-acetyloxy-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] benzoate
Summary

SMILES: COC[C@]12CC[C@@H]([C@@]34[C@@H]2[C@@H](OC)[C@@H]([C@H]3N(C1)C)[C@@]1([C@@H]2[C@H]4C[C@@]([C@@H]2OC(=O)c2ccccc2)([C@H](C1)OC)O)OC(=O)C)OC
InChI: InChI=1S/C33H45NO9/c1-18(35)43-32-15-22(40-5)31(37)14-20(23(32)28(31)42-29(36)19-10-8-7-9-11-19)33-21(39-4)12-13-30(17-38-3)16-34(2)27(33)24(32)25(41-6)26(30)33/h7-11,20-28,37H,12-17H2,1-6H3/t20-,21+,22+,23-,24+,25+,26-,27-,28-,30+,31+,32-,33+/m1/s1
InChIKey: REVYTWNGZDPRKE-PFOCBDCYSA-N
DeepSMILES: COC[C@@]CC[C@@H][C@@][C@@H]6[C@@H]OC))[C@@H][C@H]5NC%11)C)))[C@@][C@@H][C@H]7C[C@@][C@@H]5OC=O)cccccc6)))))))))[C@H]C7)OC)))O)))))OC=O)C))))))))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: COC; CO; CC(=O)OC; 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:
delphinine
External chemical identifiers:
CID:CID_102239725
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(1S,2R,3R,4R,5S,6S,8R,9R,10R,13S,16S,17R,18R)-8-acetyloxy-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-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 599.72
Log P RDKit 2.32
Topological polar surface area (Å2) RDKit 112.99
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 33
Number of heavy atoms RDKit 43
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 13
Stereochemical complexity RDKit 0.39
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 25
Shape complexity RDKit 0.76
Number of rotatable bonds RDKit 10
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,5S,6S,8R,9R,10R,13S,16S,17R,18R)-8-acetyloxy-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-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 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.45
[(1S,2R,3R,4R,5S,6S,8R,9R,10R,13S,16S,17R,18R)-8-acetyloxy-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-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 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.64
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes