IMPPAT Phytochemical information: 
[(2R,3R,5R,8R,10R,17R)-8-acetyloxy-5,7-dihydroxy-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
[(2R,3R,5R,8R,10R,17R)-8-acetyloxy-5,7-dihydroxy-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: COCC12CCC(C34[C@@H]2C(OC)C([C@H]3N(C1)C)[C@@]1([C@@H]2[C@H]4C[C@@](C2OC(=O)c2ccccc2)(C(C1O)OC)O)OC(=O)C)OC
InChI: InChI=1S/C33H45NO10/c1-17(35)44-33-21-19(14-31(38,28(42-6)26(33)36)27(21)43-29(37)18-10-8-7-9-11-18)32-20(40-4)12-13-30(16-39-3)15-34(2)25(32)22(33)23(41-5)24(30)32/h7-11,19-28,36,38H,12-16H2,1-6H3/t19-,20?,21-,22?,23?,24-,25-,26?,27?,28?,30?,31-,32?,33-/m1/s1
InChIKey: FIDOCHXHMJHKRW-PYHVONRRSA-N
DeepSMILES: COCCCCCC[C@@H]6COC))C[C@H]5NC%11)C)))[C@@][C@@H][C@H]7C[C@@]C5OC=O)cccccc6)))))))))CC7O))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: CC(=O)OC; CN(C)C; CO; COC; 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:
hypaconitine
External chemical identifiers:
CID:23337
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(2R,3R,5R,8R,10R,17R)-8-acetyloxy-5,7-dihydroxy-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 615.72
Log P RDKit 1.29
Topological polar surface area (Å2) RDKit 133.22
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 33
Number of heavy atoms RDKit 44
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 14
Stereochemical complexity RDKit 0.42
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
[(2R,3R,5R,8R,10R,17R)-8-acetyloxy-5,7-dihydroxy-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 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.4101
[(2R,3R,5R,8R,10R,17R)-8-acetyloxy-5,7-dihydroxy-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
ADMET 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 High
Log Kp (Skin permeation, cm/s) SwissADME -9.43
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes
[(2R,3R,5R,8R,10R,17R)-8-acetyloxy-5,7-dihydroxy-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
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000222982CYP3A5700
ENSP00000237612ABCG2700
ENSP00000252945CYP2E1700
ENSP00000262186KCNH2800
ENSP00000265724ABCB1700
ENSP00000337915CYP3A4700
ENSP00000342007CYP1A2700
ENSP00000353820CYP2D6700
ENSP00000360317CYP2C8700
ENSP00000360372CYP2C19700
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.