Secondary metabolite: Cis-3-(4-hydroxyphenyl)-4-isobutyldihydrofuran-2,5-dione



Cis-3-(4-hydroxyphenyl)-4-isobutyldihydrofuran-2,5-dione
Summary
Molecular formula: C14H16O4
SMILES: CC(C[C@@H]1C(=O)OC(=O)[C@@H]1c1ccc(cc1)O)C
InChI: InChI=1S/C14H16O4/c1-8(2)7-11-12(14(17)18-13(11)16)9-3-5-10(15)6-4-9/h3-6,8,11-12,15H,7H2,1-2H3/t11-,12+/m0/s1
InChIKey: KZLFRVFXQHOHPP-NWDGAFQWSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Benzenoids
Class: Phenols
Sub class: 1-hydroxy-2-unsubstituted benzenoids
Synonymous chemical names:
cis-3-(4-hydroxyphenyl)-4-isobutyldihydrofuran-2,5-dione
Chemical structure download



Cis-3-(4-hydroxyphenyl)-4-isobutyldihydrofuran-2,5-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 248.28
Log P RDKit 2.22
Topological polar surface area (Å2) RDKit 63.6
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 14
Number of heavy atoms RDKit 18
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.14
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 6
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.43
Shape complexity RDKit 0.43
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 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 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2



Cis-3-(4-hydroxyphenyl)-4-isobutyldihydrofuran-2,5-dione
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 1
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.66



Cis-3-(4-hydroxyphenyl)-4-isobutyldihydrofuran-2,5-dione
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.97
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
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