IMPPAT Phytochemical information: 
4-Hydroxy-3a,7a-dimethyl-3a,4,5,7a-tetrahydro-2-benzofuran-1(3H)-one

4-Hydroxy-3a,7a-dimethyl-3a,4,5,7a-tetrahydro-2-benzofuran-1(3H)-one
Summary

SMILES: OC1CC=CC2(C1(C)COC2=O)C
InChI: InChI=1S/C10H14O3/c1-9-5-3-4-7(11)10(9,2)6-13-8(9)12/h3,5,7,11H,4,6H2,1-2H3
InChIKey: OJIVYGKPLDUBGL-UHFFFAOYSA-N
DeepSMILES: OCCC=CCC6C)COC5=O)))))C
Scaffold Graph/Node/Bond level: O=C1OCC2CCC=CC12
Scaffold Graph/Node level: OC1OCC2CCCCC21
Scaffold Graph level: CC1CCC2CCCCC12
Functional groups: CO; CC=CC; COC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Isobenzofurans
NP Classifier Biosynthetic pathway: Terpenoids
Synonymous chemical names:
1(3h)-isobenzofuranone,3a,4,5,7a-tetrahydro-4-hydroxy-3a,7a-dimethyl-,(3aα,4β,7aα)-(.+/-.)-
External chemical identifiers:
CID:CID_41054
Chemical structure download


4-Hydroxy-3a,7a-dimethyl-3a,4,5,7a-tetrahydro-2-benzofuran-1(3H)-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 182.22
Log P RDKit 0.88
Topological polar surface area (Å2) RDKit 46.53
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 13
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.3
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.7
Number of rotatable bonds RDKit 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 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2


4-Hydroxy-3a,7a-dimethyl-3a,4,5,7a-tetrahydro-2-benzofuran-1(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 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.446521


4-Hydroxy-3a,7a-dimethyl-3a,4,5,7a-tetrahydro-2-benzofuran-1(3H)-one
ADME 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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.62
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