Secondary metabolite: Ganoleucoin AA



Ganoleucoin AA
Summary
Molecular formula: C32H42O9
SMILES: OC[C@@]1(C)C(=O)CC2[C@]3(C1CC(=O)C1=C3[C@@]2(O)[C@@H](OC(=O)C)[C@]2([C@@]1(C)C(=O)C[C@@H]2[C@@H](CCC=C(C(=O)O)C)C)C)C
InChI: InChI=1S/C32H42O9/c1-15(9-8-10-16(2)26(38)39)18-11-23(37)31(7)24-19(35)12-20-28(4,14-33)22(36)13-21-29(20,5)25(24)32(21,40)27(30(18,31)6)41-17(3)34/h10,15,18,20-21,27,33,40H,8-9,11-14H2,1-7H3,(H,38,39)/t15-,18-,20?,21?,27+,28-,29-,30+,31+,32-/m1/s1
InChIKey: ALIBLFYUASRDET-TVSZDTPLSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Triterpenoids
Synonymous chemical names:
ganoleucoin aa
Chemical structure download



Ganoleucoin AA
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 570.68
Log P RDKit 3.2
Topological polar surface area (Å2) RDKit 155.27
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 32
Number of heavy atoms RDKit 41
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.31
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 23
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.72
Shape complexity RDKit 0.72
Number of rotatable bonds SwissADME 8
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 0
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 3
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5



Ganoleucoin AA
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
Egan filter RDKit Bad
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 0.31



Ganoleucoin AA
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
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 -8.47
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 No
P-glycoprotein substrate SwissADME No




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