IMPPAT Phytochemical information: 
Withanolide B
Withanolide B
Summary

SMILES: CC1=C(C)C(=O)O[C@H](C1)[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2[C@@H]2O[C@@H]2[C@@]2([C@]1(C)C(=O)C=CC2)O)C
InChI: InChI=1S/C28H38O5/c1-14-13-20(32-25(30)15(14)2)16(3)17-8-9-18-22-19(10-12-26(17,18)4)27(5)21(29)7-6-11-28(27,31)24-23(22)33-24/h6-7,16-20,22-24,31H,8-13H2,1-5H3/t16-,17+,18-,19-,20+,22-,23-,24-,26+,27-,28-/m0/s1
InChIKey: ZTEVDTFJUUJBLP-MBMSZCMESA-N
DeepSMILES: CC=CC)C=O)O[C@H]C6)[C@H][C@H]CC[C@@H][C@]5C)CC[C@H][C@H]6[C@@H]O[C@@H]3[C@@][C@]7C)C=O)C=CC6)))))O))))))))))))))C
Scaffold Graph/Node/Bond level: O=C1C=CCC(CC2CCC3C2CCC2C4C(=O)C=CCC4C4OC4C32)O1
Scaffold Graph/Node level: OC1CCCC(CC2CCC3C2CCC2C4C(O)CCCC4C4OC4C32)O1
Scaffold Graph level: CC1CCCC(CC2CCC3C2CCC2C4C(C)CCCC4C4CC4C32)C1
Functional groups: CC1=C(C)C(=O)OCC1; C[C@@H]1O[C@@H]1C; CC=CC(=O)C; CO
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:
withanolides b, Lycium substance B, withanolide b, lycium substance b
External chemical identifiers:
CID:CID_14236711; ChEBI:CHEBI:175627; ZINC:ZINC000095913389; FDASRS:9YU877VU8K; MolPort-046-683-997
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Withanolide B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 454.61
Log P RDKit 4.38
Topological polar surface area (Å2) RDKit 76.13
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
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 11
Stereochemical complexity RDKit 0.39
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 22
Shape complexity RDKit 0.79
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 3
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Withanolide B
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 1
Ghose filter RDKit Failed
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 0.494981
Withanolide B
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 -5.76
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 No
P-glycoprotein substrate SwissADME Yes