Secondary metabolite: 4-Hydroxy-3-methoxy-2-(3-methylbut-2-en-1-yl)phenyl 2,4-dihydroxy-6-methylbenzoate



4-Hydroxy-3-methoxy-2-(3-methylbut-2-en-1-yl)phenyl 2,4-dihydroxy-6-methylbenzoate
Summary
Molecular formula: C20H22O6
SMILES: COc1c(O)ccc(c1CC=C(C)C)OC(=O)c1c(C)cc(cc1O)O
InChI: InChI=1S/C20H22O6/c1-11(2)5-6-14-17(8-7-15(22)19(14)25-4)26-20(24)18-12(3)9-13(21)10-16(18)23/h5,7-10,21-23H,6H2,1-4H3
InChIKey: RGGLERSJYRMVRI-UHFFFAOYSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Phenylpropanoids and polyketides
Class: Depsides and depsidones
Synonymous chemical names:
4-hydroxy-3-methoxy-2-(3-methylbut-2-en-1-yl)phenyl 2,4-dihydroxy-6-methylbenzoate
Chemical structure download



4-Hydroxy-3-methoxy-2-(3-methylbut-2-en-1-yl)phenyl 2,4-dihydroxy-6-methylbenzoate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 358.39
Log P RDKit 3.85
Topological polar surface area (Å2) RDKit 96.22
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 6
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 15
Number of sp3 hybridized carbon atoms RDKit 5
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.25
Shape complexity RDKit 0.25
Number of rotatable bonds SwissADME 6
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 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
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 2



4-Hydroxy-3-methoxy-2-(3-methylbut-2-en-1-yl)phenyl 2,4-dihydroxy-6-methylbenzoate
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 Good
Number of Leadlikeness violations SwissADME 2
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.43



4-Hydroxy-3-methoxy-2-(3-methylbut-2-en-1-yl)phenyl 2,4-dihydroxy-6-methylbenzoate
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 -4.88
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 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