Secondary metabolite: Epi-phelligrin A



Epi-phelligrin A
Summary
Molecular formula: C22H18O6
SMILES: Oc1ccc(cc1)[C@@H]1CC(=O)c2c(O1)cc(c(c2O)Cc1ccccc1O)O
InChI: InChI=1S/C22H18O6/c23-14-7-5-12(6-8-14)19-11-18(26)21-20(28-19)10-17(25)15(22(21)27)9-13-3-1-2-4-16(13)24/h1-8,10,19,23-25,27H,9,11H2/t19-/m0/s1
InChIKey: OEPZGPZSYKMOSV-IBGZPJMESA-N
Chemical classification
Kingdom: Organic compounds
Super class: Phenylpropanoids and polyketides
Class: Diarylheptanoids
Sub class: Linear diarylheptanoids
Synonymous chemical names:
epi-phelligrin a
Chemical structure download



Epi-phelligrin A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 378.38
Log P RDKit 3.81
Topological polar surface area (Å2) RDKit 107.22
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 19
Number of sp3 hybridized carbon atoms RDKit 3
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.14
Shape complexity RDKit 0.14
Number of rotatable bonds SwissADME 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
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 4



Epi-phelligrin 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
Egan filter RDKit Good
Pfizer’s 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Number of Leadlikeness violations SwissADME 2
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.55



Epi-phelligrin A
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.7
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No




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