Secondary metabolite: Fomitoside I



Fomitoside I
Summary
Molecular formula: C36H58O8
SMILES: OC[C@H]1O[C@@H](O)[C@@H]([C@H]([C@@H]1O)O)OC(=O)[C@@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CC[C@H](C2(C)C)O)C)CCC=C(C)C
InChI: InChI=1S/C36H58O8/c1-20(2)9-8-10-21(31(41)44-30-29(40)28(39)25(19-37)43-32(30)42)22-13-17-36(7)24-11-12-26-33(3,4)27(38)15-16-34(26,5)23(24)14-18-35(22,36)6/h9,21-22,25-30,32,37-40,42H,8,10-19H2,1-7H3/t21-,22-,25-,26+,27-,28-,29+,30-,32-,34-,35-,36+/m1/s1
InChIKey: JIESWXRJWVOIGO-NLXUJKFSSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Triterpenoids
Synonymous chemical names:
fomitoside i
Chemical structure download



Fomitoside I
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 618.85
Log P RDKit 4.8
Topological polar surface area (Å2) RDKit 136.68
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 36
Number of heavy atoms RDKit 44
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 12
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 31
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.86
Shape complexity RDKit 0.86
Number of rotatable bonds SwissADME 8
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 2
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5



Fomitoside I
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 3
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.2



Fomitoside I
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly 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 -6.06
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