Secondary metabolite: Isohericerin



Isohericerin
Summary
Molecular formula: C27H33NO3
SMILES: COc1cc2C(=O)N(Cc2c(c1CC=C(CCC=C(C)C)C)O)CCc1ccccc1
InChI: InChI=1S/C27H33NO3/c1-19(2)9-8-10-20(3)13-14-22-25(31-4)17-23-24(26(22)29)18-28(27(23)30)16-15-21-11-6-5-7-12-21/h5-7,9,11-13,17,29H,8,10,14-16,18H2,1-4H3
InChIKey: AYUFSIRZXDWSDR-UHFFFAOYSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Organoheterocyclic compounds
Class: Isoindoles and derivatives
Sub class: Isoindolines
Synonymous chemical names:
isohericerin
Chemical structure download



Isohericerin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 419.56
Log P RDKit 5.83
Topological polar surface area (Å2) RDKit 49.77
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 4
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 17
Number of sp3 hybridized carbon atoms RDKit 10
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.37
Shape complexity RDKit 0.37
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 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3



Isohericerin
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 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Egan filter RDKit Good
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 0.52



Isohericerin
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -4.38
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 Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes




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