Secondary metabolite: (2')-(Z)-5-(3'-hydroxymethyl-3'-methylallyloxy)-7-methoxy-6-methylphthalide



(2')-(Z)-5-(3'-hydroxymethyl-3'-methylallyloxy)-7-methoxy-6-methylphthalide
Summary
Molecular formula: C15H18O5
SMILES: OC/C(=CCOc1cc2COC(=O)c2c(c1C)OC)/C
InChI: InChI=1S/C15H18O5/c1-9(7-16)4-5-19-12-6-11-8-20-15(17)13(11)14(18-3)10(12)2/h4,6,16H,5,7-8H2,1-3H3/b9-4-
InChIKey: AKQXDTZFGGTDHR-WTKPLQERSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Organoheterocyclic compounds
Class: Isocoumarans
Sub class: Isobenzofuranones
Synonymous chemical names:
(2')-(z)-5-(3'-hydroxymethyl-3'-methylallyloxy)-7-methoxy-6-methylphthalide
Chemical structure download



(2')-(Z)-5-(3'-hydroxymethyl-3'-methylallyloxy)-7-methoxy-6-methylphthalide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 278.3
Log P RDKit 1.99
Topological polar surface area (Å2) RDKit 64.99
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 5
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 6
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.4
Shape complexity RDKit 0.4
Number of rotatable bonds SwissADME 5
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



(2')-(Z)-5-(3'-hydroxymethyl-3'-methylallyloxy)-7-methoxy-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
Pfizer’s 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Number of Leadlikeness violations SwissADME 0
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.66



(2')-(Z)-5-(3'-hydroxymethyl-3'-methylallyloxy)-7-methoxy-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 -6.65
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
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