IMPPAT Phytochemical information: 
Withanolide M
Withanolide M
Summary

SMILES: CC1=C(C)C(=O)O[C@H](C1)[C@@]([C@@]1(O)C[C@H]2[C@@]3([C@]1(C)CC[C@H]1[C@H]3CC=C3[C@]1(C)C(=O)C=CC3)O2)(O)C
InChI: InChI=1S/C28H36O6/c1-15-13-21(33-23(30)16(15)2)26(5,31)27(32)14-22-28(34-22)19-10-9-17-7-6-8-20(29)25(17,4)18(19)11-12-24(27,28)3/h6,8-9,18-19,21-22,31-32H,7,10-14H2,1-5H3/t18-,19+,21+,22-,24+,25-,26-,27+,28-/m0/s1
InChIKey: QVPVAUAXVYYQTQ-XDLKSZKHSA-N
DeepSMILES: CC=CC)C=O)O[C@H]C6)[C@@][C@@]O)C[C@H][C@@][C@]5C)CC[C@H][C@H]6CC=C[C@]6C)C=O)C=CC6)))))))))))))O3)))))O)C
Scaffold Graph/Node/Bond level: O=C1C=CCC(CC2CC3OC34C2CCC2C3C(=O)C=CCC3=CCC24)O1
Scaffold Graph/Node level: OC1CCCC(CC2CC3OC34C2CCC2C3C(O)CCCC3CCC24)O1
Scaffold Graph level: CC1CCCC(CC2CC3CC34C2CCC2C3C(C)CCCC3CCC24)C1
Functional groups: CO; CC1=C(C)C(=O)OCC1; C[C@@H]1O[C@@]1(C)C; CC=C(C)C; CC=CC(=O)C
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:
withanolide m, withanolides m, Withanolide M, 17α,20-dihydroxy-1-oxo-14α15α-epoxy-20s,22r-witha-2,5,24-trienolide (withanolide m)
External chemical identifiers:
CID:CID_25090669; ZINC:ZINC000137542724
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Withanolide M
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 468.59
Log P RDKit 3.56
Topological polar surface area (Å2) RDKit 96.36
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.32
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 20
Shape complexity RDKit 0.71
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Withanolide M
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.365501
Withanolide M
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 -7.43
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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