IMPPAT Phytochemical information: 
Withanolide N
Withanolide N
Summary

SMILES: OCC1=C(C)C[C@@H](OC1=O)[C@H]([C@@]1(O)CC=C2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)C(=O)C=CC2)C
InChI: InChI=1S/C28H36O5/c1-16-14-23(33-25(31)20(16)15-29)17(2)28(32)13-11-21-19-9-8-18-6-5-7-24(30)27(18,4)22(19)10-12-26(21,28)3/h5,7-8,11,17,19,22-23,29,32H,6,9-10,12-15H2,1-4H3/t17-,19+,22+,23-,26+,27+,28+/m1/s1
InChIKey: FIQAJJNJIBXRNB-ALUBXIJSSA-N
DeepSMILES: OCC=CC)C[C@@H]OC6=O)))[C@H][C@@]O)CC=C[C@]5C)CC[C@H][C@H]6CC=C[C@]6C)C=O)C=CC6)))))))))))))))))C
Scaffold Graph/Node/Bond level: O=C1C=CCC(CC2CC=C3C2CCC2C3CC=C3CC=CC(=O)C32)O1
Scaffold Graph/Node level: OC1CCCC(CC2CCC3C2CCC2C3CCC3CCCC(O)C32)O1
Scaffold Graph level: CC1CCCC(CC2CCC3C2CCC2C3CCC3CCCC(C)C32)C1
Functional groups: CO; CC1=C(C)C(=O)OCC1; 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 n, 17α,27-dihydroxy-1-oxo-20R,22R-witha-2,5,14,24-tetraenolide (withanolide N)
External chemical identifiers:
CID:CID_23266147; SureChEMBL:SCHEMBL2231874
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Withanolide N
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 452.59
Log P RDKit 4.21
Topological polar surface area (Å2) RDKit 83.83
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 18
Shape complexity RDKit 0.64
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Withanolide N
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.5
Withanolide N
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 -6.62
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes