Secondary metabolite: (3aR,6S,7R,7aS)-6,7-dihydroxy-6-methyl-3-methylenehexahydrobenzofuran-2(3h)-one



(3aR,6S,7R,7aS)-6,7-dihydroxy-6-methyl-3-methylenehexahydrobenzofuran-2(3h)-one
Summary
Molecular formula: C10H14O4
SMILES: O=C1O[C@H]2[C@@H](C1=C)CC[C@]([C@@H]2O)(C)O
InChI: InChI=1S/C10H14O4/c1-5-6-3-4-10(2,13)8(11)7(6)14-9(5)12/h6-8,11,13H,1,3-4H2,2H3/t6-,7+,8-,10+/m1/s1
InChIKey: ZVMVPIWZXUSVAO-JIOCBJNQSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Organoheterocyclic compounds
Class: Benzofurans
Synonymous chemical names:
(3ar,6s,7r,7as)-6,7-dihydroxy-6-methyl-3-methylenehexahydrobenzofuran-2(3h)-one
Chemical structure download



(3aR,6S,7R,7aS)-6,7-dihydroxy-6-methyl-3-methylenehexahydrobenzofuran-2(3h)-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 198.22
Log P RDKit -0.01
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 10
Number of heavy atoms RDKit 14
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.4
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 7
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.7
Shape complexity RDKit 0.7
Number of rotatable bonds SwissADME 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2



(3aR,6S,7R,7aS)-6,7-dihydroxy-6-methyl-3-methylenehexahydrobenzofuran-2(3h)-one
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 1
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.42



(3aR,6S,7R,7aS)-6,7-dihydroxy-6-methyl-3-methylenehexahydrobenzofuran-2(3h)-one
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.47
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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