Secondary metabolite: Phelliribsin A



Phelliribsin A
Summary
Molecular formula: C22H16O7
SMILES: Oc1cc(/C=C/C2=CC(=O)C3(O2)C(=Cc2c3cc(O)c(c2)O)C(=O)C)ccc1O
InChI: InChI=1S/C22H16O7/c1-11(23)15-7-13-8-19(26)20(27)10-16(13)22(15)21(28)9-14(29-22)4-2-12-3-5-17(24)18(25)6-12/h2-10,24-27H,1H3/b4-2+
InChIKey: HCUSHIWVGLUDLU-DUXPYHPUSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Benzenoids
Class: Indenes and isoindenes
Synonymous chemical names:
phelliribsin a
Chemical structure download



Phelliribsin A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 392.36
Log P RDKit 2.89
Topological polar surface area (Å2) RDKit 124.29
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 7
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 20
Number of sp3 hybridized carbon atoms RDKit 2
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.09
Shape complexity RDKit 0.09
Number of rotatable bonds SwissADME 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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



Phelliribsin 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 0.59



Phelliribsin A
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 -7.02
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No




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