Secondary metabolite: Erinacerin D



Erinacerin D
Summary
Molecular formula: C20H25NO6
SMILES: OCCN1Cc2c(C1=O)cc(c(c2O)C/C=C(/CC/C=C(/C(=O)O)C)C)O
InChI: InChI=1S/C20H25NO6/c1-12(4-3-5-13(2)20(26)27)6-7-14-17(23)10-15-16(18(14)24)11-21(8-9-22)19(15)25/h5-6,10,22-24H,3-4,7-9,11H2,1-2H3,(H,26,27)/b12-6+,13-5+
InChIKey: WFUALHCWGPSZPU-YKNDAMCPSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Organoheterocyclic compounds
Class: Isoindoles and derivatives
Sub class: Isoindolines
Synonymous chemical names:
erinacerin d
Chemical structure download



Erinacerin D
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 375.42
Log P RDKit 2.35
Topological polar surface area (Å2) RDKit 118.3
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 8
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.4
Shape complexity RDKit 0.4
Number of rotatable bonds SwissADME 8
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 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2



Erinacerin D
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 2
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.41



Erinacerin D
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
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 -7.14
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
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