Secondary metabolite: Melleolide M



Melleolide M
Summary
Molecular formula: C23H29ClO7
SMILES: OCC1=C[C@@H]2CC([C@@H]([C@@H]2[C@@]2([C@@]1(O)[C@H](OC(=O)c1c(O)cc(c(c1C)Cl)O)C2)C)O)(C)C
InChI: InChI=1S/C23H29ClO7/c1-10-16(13(26)6-14(27)18(10)24)20(29)31-15-8-22(4)17-11(7-21(2,3)19(17)28)5-12(9-25)23(15,22)30/h5-6,11,15,17,19,25-28,30H,7-9H2,1-4H3/t11-,15-,17-,19-,22-,23+/m1/s1
InChIKey: PBSFHHQIJGTBQH-NDVLAHOZSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Sesquiterpenoids
Synonymous chemical names:
melleolide m
Chemical structure download



Melleolide M
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 452.93
Log P RDKit 2.68
Topological polar surface area (Å2) RDKit 127.45
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 31
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 0.26
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 14
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.61
Shape complexity RDKit 0.61
Number of rotatable bonds SwissADME 4
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 M
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
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 0.35



Melleolide M
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.73
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