Secondary metabolite: Lepiotaprocerin A



Lepiotaprocerin A
Summary
Molecular formula: C32H44O6
SMILES: CC(=O)O[C@H]1C[C@@]2([C@]([C@H]1[C@@H](CCC=C(C(=O)O)C)C)(C)C[C@@H]1C3=C2CC[C@@H]2[C@]3(C)C(=CC(=O)C2(C)C)O1)C
InChI: InChI=1S/C32H44O6/c1-17(10-9-11-18(2)28(35)36)26-21(37-19(3)33)15-30(6)20-12-13-23-29(4,5)24(34)14-25-32(23,8)27(20)22(38-25)16-31(26,30)7/h11,14,17,21-23,26H,9-10,12-13,15-16H2,1-8H3,(H,35,36)/t17-,21+,22-,23+,26+,30+,31-,32-/m1/s1
InChIKey: RQMCCRUYISGPCT-GOTRNUGLSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Triterpenoids
Synonymous chemical names:
lepiotaprocerin a
Chemical structure download



Lepiotaprocerin A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 524.7
Log P RDKit 6.41
Topological polar surface area (Å2) RDKit 89.9
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 32
Number of heavy atoms RDKit 38
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
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 23
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.72
Shape complexity RDKit 0.72
Number of rotatable bonds SwissADME 7
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 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5



Lepiotaprocerin A
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 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 0.25



Lepiotaprocerin A
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
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 -5.54
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
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