Secondary metabolite: Phellifuropyranone A



Phellifuropyranone A
Summary
Molecular formula: C21H14O7
SMILES: Oc1ccc(cc1O)/C=C/c1oc(=O)c2c(c1)oc(c2)c1ccc(c(c1)O)O
InChI: InChI=1S/C21H14O7/c22-15-5-2-11(7-17(15)24)1-4-13-9-20-14(21(26)27-13)10-19(28-20)12-3-6-16(23)18(25)8-12/h1-10,22-25H/b4-1+
InChIKey: LYKVAAQTDREPSC-DAFODLJHSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Organoheterocyclic compounds
Class: Furopyrans
Synonymous chemical names:
phellifuropyranone a
Chemical structure download



Phellifuropyranone A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 378.34
Log P RDKit 4.05
Topological polar surface area (Å2) RDKit 124.27
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
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 21
Number of sp3 hybridized carbon atoms RDKit 0
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0
Shape complexity RDKit 0
Number of rotatable bonds SwissADME 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 4
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



Phellifuropyranone 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 Bad
GSK 4/400 filter RDKit Bad
Number of Leadlikeness violations SwissADME 2
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.4



Phellifuropyranone 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 -6.1
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
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