Secondary metabolite: Erinacerin I



Erinacerin I
Summary
Molecular formula: C18H23NO6
SMILES: OCCN1Cc2c(C1=O)cc(c(c2O)C/C=C(/CCC(=O)OC)C)O
InChI: InChI=1S/C18H23NO6/c1-11(4-6-16(22)25-2)3-5-12-15(21)9-13-14(17(12)23)10-19(7-8-20)18(13)24/h3,9,20-21,23H,4-8,10H2,1-2H3/b11-3+
InChIKey: DSGSGFVHXMECPA-QDEBKDIKSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Organoheterocyclic compounds
Class: Isoindoles and derivatives
Sub class: Isoindolines
Synonymous chemical names:
erinacerin i
Chemical structure download



Erinacerin I
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 349.38
Log P RDKit 1.49
Topological polar surface area (Å2) RDKit 107.3
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 25
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 10
Number of sp3 hybridized carbon atoms RDKit 8
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.44
Shape complexity RDKit 0.44
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 I
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 0.51



Erinacerin I
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 -7.57
Number of PAINS structural alerts SwissADME 1
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 No
P-glycoprotein substrate SwissADME Yes




Designed by R.P. Vivek-Ananth, M Karthikeyan and Ajaya Kumar Sahoo