Secondary metabolite: Fomitoside D



Fomitoside D
Summary
Molecular formula: C36H56O7
SMILES: O=C([C@@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)CCC(=C)C(C)C)O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O
InChI: InChI=1S/C36H56O7/c1-20(2)21(3)9-10-22(31(41)43-32-30(40)29(39)26(37)19-42-32)23-13-17-36(8)25-11-12-27-33(4,5)28(38)15-16-34(27,6)24(25)14-18-35(23,36)7/h20,22-23,26-27,29-30,32,37,39-40H,3,9-19H2,1-2,4-8H3/t22-,23-,26-,27+,29+,30-,32+,34-,35-,36+/m1/s1
InChIKey: CLWQVULZKKQARP-CSAJRJIWSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Triterpenoids
Synonymous chemical names:
fomitoside d
Chemical structure download



Fomitoside D
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 600.84
Log P RDKit 5.9
Topological polar surface area (Å2) RDKit 113.29
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 36
Number of heavy atoms RDKit 43
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.28
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 30
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.83
Shape complexity RDKit 0.83
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 D
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
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 3
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.25



Fomitoside D
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 -5.75
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