Secondary metabolite: Lepistamide C



Lepistamide C
Summary
Molecular formula: C17H24N2O4
SMILES: CO[C@@]1(NC(=O)[C@@](NC1=O)(OC)CC(C)C)Cc1ccccc1
InChI: InChI=1S/C17H24N2O4/c1-12(2)10-16(22-3)14(20)19-17(23-4,15(21)18-16)11-13-8-6-5-7-9-13/h5-9,12H,10-11H2,1-4H3,(H,18,21)(H,19,20)/t16-,17-/m0/s1
InChIKey: BMACKMSINBGRRE-IRXDYDNUSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Organic acids and derivatives
Class: Carboxylic acids and derivatives
Sub class: Amino acids, peptides, and analogues
Synonymous chemical names:
lepistamide c
Chemical structure download



Lepistamide C
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 320.39
Log P RDKit 1.21
Topological polar surface area (Å2) RDKit 76.66
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.12
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 9
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.53
Shape complexity RDKit 0.53
Number of rotatable bonds SwissADME 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2



Lepistamide 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 Good
Pfizer’s 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Number of Leadlikeness violations SwissADME 0
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.83



Lepistamide C
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.87
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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