Secondary metabolite: 3R-(2R-hydroxypropyl)-8-hydroxyl-7-methyl-3,4-dihydroisocoumarine



3R-(2R-hydroxypropyl)-8-hydroxyl-7-methyl-3,4-dihydroisocoumarine
Summary
Molecular formula: C13H16O4
SMILES: C[C@H](C[C@@H]1OC(=O)c2c(C1)ccc(c2O)C)O
InChI: InChI=1S/C13H16O4/c1-7-3-4-9-6-10(5-8(2)14)17-13(16)11(9)12(7)15/h3-4,8,10,14-15H,5-6H2,1-2H3/t8-,10+/m1/s1
InChIKey: WDCHVRICDGHOKM-SCZZXKLOSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Organoheterocyclic compounds
Class: Benzopyrans
Sub class: 2-benzopyrans
Synonymous chemical names:
3r-(2r-hydroxypropyl)-8-hydroxyl-7-methyl-3,4-dihydroisocoumarine
Chemical structure download



3R-(2R-hydroxypropyl)-8-hydroxyl-7-methyl-3,4-dihydroisocoumarine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 236.27
Log P RDKit 1.55
Topological polar surface area (Å2) RDKit 66.76
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 13
Number of heavy atoms RDKit 17
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 0.15
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 6
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.46
Shape complexity RDKit 0.46
Number of rotatable bonds SwissADME 2
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



3R-(2R-hydroxypropyl)-8-hydroxyl-7-methyl-3,4-dihydroisocoumarine
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 0.76



3R-(2R-hydroxypropyl)-8-hydroxyl-7-methyl-3,4-dihydroisocoumarine
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 -5.94
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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