Secondary metabolite: Leiwansterol B



Leiwansterol B
Summary
Molecular formula: C29H46O4
SMILES: CC[C@@H](C(C)C)/C=C/[C@H]([C@H]1C[C@@H](C2=C3[C@@](CC[C@]12C)(O)[C@@]1(C)CC[C@@H](C[C@@H]1CC3=O)O)O)C
InChI: InChI=1S/C29H46O4/c1-7-19(17(2)3)9-8-18(4)22-16-24(32)25-26-23(31)15-20-14-21(30)10-11-28(20,6)29(26,33)13-12-27(22,25)5/h8-9,17-22,24,30,32-33H,7,10-16H2,1-6H3/b9-8+/t18-,19-,20-,21+,22-,24+,27-,28+,29-/m1/s1
InChIKey: BIDNVTVZCOKKAF-FAGXQHCLSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Steroids and steroid derivatives
Sub class: Stigmastanes and derivatives
Synonymous chemical names:
leiwansterol b
Chemical structure download



Leiwansterol B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 458.68
Log P RDKit 5.21
Topological polar surface area (Å2) RDKit 77.76
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 29
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.31
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 24
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.83
Shape complexity RDKit 0.83
Number of rotatable bonds SwissADME 5
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4



Leiwansterol B
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 2
Ghose filter RDKit Failed
Veber filter RDKit Good
Egan filter RDKit Good
Pfizer’s 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Number of Leadlikeness violations SwissADME 2
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.49



Leiwansterol B
ADMET 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 -6.02
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 No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes




Designed by R.P. Vivek-Ananth, M Karthikeyan and Ajaya Kumar Sahoo