Secondary metabolite: Melleolide C



Melleolide C
Summary
Molecular formula: C24H32O8
SMILES: COc1cc(C)c(c(c1)O)C(=O)O[C@@H]1C[C@]2([C@]1(O)C(=C[C@]1([C@@H]2[C@@H](O)C(C1)(C)C)O)CO)C
InChI: InChI=1S/C24H32O8/c1-12-6-14(31-5)7-15(26)17(12)20(28)32-16-9-22(4)18-19(27)21(2,3)11-23(18,29)8-13(10-25)24(16,22)30/h6-8,16,18-19,25-27,29-30H,9-11H2,1-5H3/t16-,18-,19-,22-,23+,24+/m1/s1
InChIKey: XXMVVKDVYBWXPQ-QSNWBFGMSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Sesquiterpenoids
Synonymous chemical names:
melleolide c
Chemical structure download



Melleolide C
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 448.51
Log P RDKit 1.45
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 24
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 15
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.62
Shape complexity RDKit 0.62
Number of rotatable bonds SwissADME 5
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
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



Melleolide C
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Egan filter RDKit Bad
Pfizer’s 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Number of Leadlikeness violations SwissADME 1
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.34



Melleolide C
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.68
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 Yes




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