IMPPAT Phytochemical information: 
(2S,3R,5R,6S)-2-[(2R,3R,4S,5S,6R)-4-hydroxy-2-(hydroxymethyl)-6-[[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-y
(2S,3R,5R,6S)-2-[(2R,3R,4S,5S,6R)-4-hydroxy-2-(hydroxymethyl)-6-[[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-y
Summary

SMILES: OC[C@H]1O[C@@H](O[C@H]2CC[C@]3(C(=CC[C@@H]4[C@@H]3CC[C@]3([C@H]4C[C@H]4[C@@H]3[C@H](C)[C@@H]3N4C[C@H](CC3)C)C)C2)C)[C@H]([C@H]([C@H]1O[C@@H]1O[C@@H](C)[C@@H](C([C@H]1O)O)O)O)O[C@@H]1O[C@@H](C)[C@H]([C@H]([C@H]1O)O)O
InChI: InChI=1S/C45H73NO14/c1-19-7-10-28-20(2)31-29(46(28)17-19)16-27-25-9-8-23-15-24(11-13-44(23,5)26(25)12-14-45(27,31)6)57-43-40(60-42-37(53)35(51)33(49)22(4)56-42)38(54)39(30(18-47)58-43)59-41-36(52)34(50)32(48)21(3)55-41/h8,19-22,24-43,47-54H,7,9-18H2,1-6H3/t19-,20+,21-,22-,24-,25+,26-,27-,28+,29-,30+,31-,32-,33+,34?,35+,36+,37+,38-,39-,40-,41-,42-,43+,44-,45-/m0/s1
InChIKey: TYNQWWGVEGFKRU-MSHZQAJZSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@H]CC[C@]C=CC[C@@H][C@@H]6CC[C@][C@H]6C[C@H][C@@H]5[C@H]C)[C@@H]N5C[C@H]CC6))C))))))))))C))))))))C6))C))))))[C@H][C@H][C@H]6O[C@@H]O[C@@H]C)[C@@H]C[C@H]6O))O))O)))))))O))O[C@@H]O[C@@H]C)[C@H][C@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: C1=C2CC(OC3OCC(OC4CCCCO4)CC3OC3CCCCO3)CCC2C2CCC3C(CC4C3CC3CCCCN34)C2C1
Scaffold Graph/Node level: C1CCC(OC2COC(OC3CCC4C(CCC5C4CCC4C5CC5C4CC4CCCCN45)C3)C(OC3CCCCO3)C2)OC1
Scaffold Graph level: C1CCC(CC2CCC(CC3CCC4C(CCC5C4CCC4C6CC7CCCCC7C6CC54)C3)C(CC3CCCCC3)C2)CC1
Functional groups: CC=C(C)C; CN(C)C; CO; CO[C@@H](C)OC; CO[C@H](C)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Steroidal glycosides
NP Classifier Biosynthetic pathway: Alkaloids|Terpenoids
NP Classifier Superclass: Pseudoalkaloids
NP Classifier Class: Steroidal alkaloids
Synonymous chemical names:
alpha-chaconine, α-chaconine
External chemical identifiers:
CID:129627776
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(2S,3R,5R,6S)-2-[(2R,3R,4S,5S,6R)-4-hydroxy-2-(hydroxymethyl)-6-[[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-y
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 852.07
Log P RDKit 1.18
Topological polar surface area (Å2) RDKit 220.46
Number of hydrogen bond acceptors RDKit 15
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 45
Number of heavy atoms RDKit 60
Number of heteroatoms RDKit 15
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 26
Stereochemical complexity RDKit 0.58
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 2
Number of sp3 hybridized carbon atoms RDKit 43
Shape complexity RDKit 0.96
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 5
Number of aliphatic rings RDKit 9
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 9
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 5
Number of saturated rings RDKit 8
Number of Smallest Set of Smallest Rings (SSSR) RDKit 9
(2S,3R,5R,6S)-2-[(2R,3R,4S,5S,6R)-4-hydroxy-2-(hydroxymethyl)-6-[[(1S,2S,7S,10R,11S,14S,15R,16S,17R,20S,23S)-10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.02,11.05,10.015,23.017,22]tetracos-4-en-7-y
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
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 0.1688