Secondary metabolite: 5-(3',3'-Dimethylallyloxy)-7-hydroxy-6-methylphthalide



5-(3',3'-Dimethylallyloxy)-7-hydroxy-6-methylphthalide
Summary
Molecular formula: C14H16O4
SMILES: CC(=CCOc1cc2COC(=O)c2c(c1C)O)C
InChI: InChI=1S/C14H16O4/c1-8(2)4-5-17-11-6-10-7-18-14(16)12(10)13(15)9(11)3/h4,6,15H,5,7H2,1-3H3
InChIKey: OBLRTUOESOIUPD-UHFFFAOYSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Organoheterocyclic compounds
Class: Isocoumarans
Sub class: Isobenzofuranones
Synonymous chemical names:
5-(3',3'-dimethylallyloxy)-7-hydroxy-6-methylphthalide
Chemical structure download



5-(3',3'-Dimethylallyloxy)-7-hydroxy-6-methylphthalide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 248.28
Log P RDKit 2.72
Topological polar surface area (Å2) RDKit 55.76
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 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 5
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.36
Shape complexity RDKit 0.36
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 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2



5-(3',3'-Dimethylallyloxy)-7-hydroxy-6-methylphthalide
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



5-(3',3'-Dimethylallyloxy)-7-hydroxy-6-methylphthalide
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 -5.41
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
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