Secondary metabolite: Cordycecin A



Cordycecin A
Summary
Molecular formula: C33H57N3O9
SMILES: CC(C[C@@H]1NC(=O)[C@H](OC(=O)[C@H](CC(C)C)NC(=O)[C@H](OC(=O)[C@@H](NC(=O)[C@H](OC1=O)C(C)C)CC(C)C)C(C)C)C(C)C)C
InChI: InChI=1S/C33H57N3O9/c1-16(2)13-22-31(40)43-26(20(9)10)29(38)35-24(15-18(5)6)33(42)45-27(21(11)12)30(39)36-23(14-17(3)4)32(41)44-25(19(7)8)28(37)34-22/h16-27H,13-15H2,1-12H3,(H,34,37)(H,35,38)(H,36,39)/t22-,23-,24-,25+,26+,27+/m0/s1
InChIKey: WBSKRKWHUWMBFP-VYLWARHZSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Organic acids and derivatives
Class: Peptidomimetics
Sub class: Depsipeptides
Synonymous chemical names:
cordycecin a
Chemical structure download



Cordycecin A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 639.83
Log P RDKit 3.3
Topological polar surface area (Å2) RDKit 166.2
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 33
Number of heavy atoms RDKit 45
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 3
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 27
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.82
Shape complexity RDKit 0.82
Number of rotatable bonds SwissADME 9
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 1
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 1



Cordycecin A
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 3
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 3
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.25



Cordycecin A
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -5.19
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