Secondary metabolite: Eryngiolide A



Eryngiolide A
Summary
Molecular formula: C20H30O8
SMILES: O=C1O[C@H]2[C@@H]([C@H]1C)CC[C@](C)(O)[C@H](O)[C@@H]1[C@H](CC[C@]([C@@H]2O)(C)O)C(=C)C(=O)O1
InChI: InChI=1S/C20H30O8/c1-9-11-5-7-19(3,25)16(22)14-12(10(2)18(24)28-14)6-8-20(4,26)15(21)13(11)27-17(9)23/h10-16,21-22,25-26H,1,5-8H2,2-4H3/t10-,11-,12-,13+,14+,15-,16-,19+,20+/m1/s1
InChIKey: GHZVTIKGATYJRL-WZRMTEHQSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Phenylpropanoids and polyketides
Class: Macrolides and analogues
Synonymous chemical names:
eryngiolide a
Chemical structure download



Eryngiolide A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 398.45
Log P RDKit 0.06
Topological polar surface area (Å2) RDKit 133.52
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.45
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 16
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.8
Shape complexity RDKit 0.8
Number of rotatable bonds SwissADME 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3



Eryngiolide A
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 Good
Number of Leadlikeness violations SwissADME 1
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.33



Eryngiolide A
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 -8.59
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 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