IMPPAT Phytochemical information: 
Ashwagandhanolide
Ashwagandhanolide
Summary

SMILES: OCC1=C(C)C[C@@H](OC1=O)[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C[C@@H]([C@]2([C@]1(C)C(=O)C=C[C@@H]2O)O)S[C@H]1C[C@H]2[C@@H]3CC[C@@H]([C@@]3(C)CC[C@@H]2[C@@]2([C@@]1(O)[C@@H](O)C=CC2=O)C)[C@@H]([C@H]1CC(=C(C(=O)O1)CO)C)C)C
InChI: InChI=1S/C56H78O12S/c1-27-21-41(67-49(63)33(27)25-57)29(3)35-9-11-37-31-23-47(55(65)45(61)15-13-43(59)53(55,7)39(31)17-19-51(35,37)5)69-48-24-32-38-12-10-36(30(4)42-22-28(2)34(26-58)50(64)68-42)52(38,6)20-18-40(32)54(8)44(60)14-16-46(62)56(48,54)66/h13-16,29-32,35-42,45-48,57-58,61-62,65-66H,9-12,17-26H2,1-8H3/t29-,30-,31-,32-,35+,36+,37-,38-,39-,40-,41+,42+,45-,46-,47-,48-,51+,52+,53-,54-,55+,56+/m0/s1
InChIKey: OCURLCGFNKYNMO-DHHZIUIOSA-N
DeepSMILES: OCC=CC)C[C@@H]OC6=O)))[C@H][C@H]CC[C@@H][C@]5C)CC[C@H][C@H]6C[C@@H][C@][C@]6C)C=O)C=C[C@@H]6O))))))O))S[C@H]C[C@H][C@@H]CC[C@@H][C@@]5C)CC[C@@H]9[C@@][C@@]%13O)[C@@H]O)C=CC6=O))))))C))))))[C@@H][C@H]CC=CC=O)O6))CO)))C))))C)))))))))))))))))))))C
Scaffold Graph/Node/Bond level: O=C1C=CCC(CC2CCC3C2CCC2C3CC(SC3CC4C5CCC(CC6CC=CC(=O)O6)C5CCC4C4C(=O)C=CCC34)C3CC=CC(=O)C32)O1
Scaffold Graph/Node level: OC1CCCC(CC2CCC3C2CCC2C3CC(SC3CC4C5CCC(CC6CCCC(O)O6)C5CCC4C4C(O)CCCC34)C3CCCC(O)C32)O1
Scaffold Graph level: CC1CCCC(CC2CCC3C2CCC2C3CC(CC3CC4C5CCC(CC6CCCC(C)C6)C5CCC4C4C(C)CCCC34)C3CCCC(C)C32)C1
Functional groups: CC1=C(C)C(=O)OCC1; CC=CC(C)=O; CO; CSC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Steroid lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Steroids
NP Classifier Class: Ergostane steroids
Synonymous chemical names:
ashwagandhanolide
External chemical identifiers:
CID:16099532; ChEMBL:CHEMBL507211; ZINC:ZINC000255251282
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Ashwagandhanolide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 975.3
Log P RDKit 6.38
Topological polar surface area (Å2) RDKit 208.12
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 56
Number of heavy atoms RDKit 69
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 1
Number of chiral carbon atoms RDKit 22
Stereochemical complexity RDKit 0.39
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 44
Shape complexity RDKit 0.79
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 8
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 10
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 10
Number of saturated carbocycles RDKit 6
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 10
Ashwagandhanolide
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 4
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.1464