IMPPAT Phytochemical information: 
(3R,3aR,7aS)-3-Butylhexahydro-1(3H)-isobenzofuranone

(3R,3aR,7aS)-3-Butylhexahydro-1(3H)-isobenzofuranone
Summary

SMILES: CCCCC1OC(=O)C2C1CCCC2
InChI: InChI=1S/C12H20O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h9-11H,2-8H2,1H3
InChIKey: TZRMFZSOOVBPPN-UHFFFAOYSA-N
DeepSMILES: CCCCCOC=O)CC5CCCC6
Scaffold Graph/Node/Bond level: O=C1OCC2CCCCC12
Scaffold Graph/Node level: OC1OCC2CCCCC21
Scaffold Graph level: CC1CCC2CCCCC12
Functional groups: COC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Isobenzofurans
NP Classifier Biosynthetic pathway: Fatty acids
NP Classifier Superclass: Fatty acyls
NP Classifier Class: Hydrocarbons
Synonymous chemical names:
3-butylhexahydrophthalide
External chemical identifiers:
CID:CID_12367055; ChEBI:CHEBI:172047; SureChEMBL:SCHEMBL1279424
Chemical structure download


(3R,3aR,7aS)-3-Butylhexahydro-1(3H)-isobenzofuranone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 196.29
Log P RDKit 2.91
Topological polar surface area (Å2) RDKit 26.3
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 12
Number of heavy atoms RDKit 14
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 1
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.92
Number of rotatable bonds RDKit 3
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


(3R,3aR,7aS)-3-Butylhexahydro-1(3H)-isobenzofuranone
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 0.648662


(3R,3aR,7aS)-3-Butylhexahydro-1(3H)-isobenzofuranone
ADME 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 -4.98
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No