Secondary metabolite: Ganoleuconin B



Ganoleuconin B
Summary
Molecular formula: C30H44O7
SMILES: OC[C@]1(C)C(=O)CC[C@]2([C@H]1C[C@H](O)C1=C2C(=O)[C@@H]([C@]2([C@@]1(C)CC[C@@H]2[C@@H](CC/C=C(/C(=O)O)C)C)C)O)C
InChI: InChI=1S/C30H44O7/c1-16(8-7-9-17(2)26(36)37)18-10-13-29(5)22-19(32)14-20-27(3,12-11-21(33)28(20,4)15-31)23(22)24(34)25(35)30(18,29)6/h9,16,18-20,25,31-32,35H,7-8,10-15H2,1-6H3,(H,36,37)/b17-9+/t16-,18-,19+,20-,25+,27+,28+,29+,30+/m1/s1
InChIKey: KZSJJLYAVJDVEZ-BHEBFUJYSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Triterpenoids
Synonymous chemical names:
ganoleuconin b
Chemical structure download



Ganoleuconin B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 516.67
Log P RDKit 3.85
Topological polar surface area (Å2) RDKit 132.13
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 37
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.3
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 23
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.77
Shape complexity RDKit 0.77
Number of rotatable bonds SwissADME 6
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 2
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4



Ganoleuconin 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 3
Ghose filter RDKit Failed
Veber 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 0.39



Ganoleuconin B
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -6.72
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