IMPPAT Phytochemical information: 
(8S,8aS)-8-hydroxy-3,5,8a-trimethyl-6,7,8,9-tetrahydrobenzo[f][1]benzofuran-4-one
(8S,8aS)-8-hydroxy-3,5,8a-trimethyl-6,7,8,9-tetrahydrobenzo[f][1]benzofuran-4-one
Summary

SMILES: CC1=C2C(=O)c3c(C[C@@]2([C@H](CC1)O)C)occ3C
InChI: InChI=1S/C15H18O3/c1-8-4-5-11(16)15(3)6-10-12(9(2)7-18-10)14(17)13(8)15/h7,11,16H,4-6H2,1-3H3/t11-,15+/m0/s1
InChIKey: PFIXJSCFTAVWBW-XHDPSFHLSA-N
DeepSMILES: CC=CC=O)ccC[C@@]6[C@H]CC%10))O))C)))occ5C
Scaffold Graph/Node/Bond level: O=C1C2=CCCCC2Cc2occc21
Scaffold Graph/Node level: OC1C2CCCCC2CC2OCCC21
Scaffold Graph level: CC1C2CCCCC2CC2CCCC21
Functional groups: cC(=O)C(=C(C)C)C; CO; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Sesquiterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Eudesmane sesquiterpenoids
Synonymous chemical names:
Nehipetol, nehipetol
External chemical identifiers:
CID:CID_101289704
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(8S,8aS)-8-hydroxy-3,5,8a-trimethyl-6,7,8,9-tetrahydrobenzo[f][1]benzofuran-4-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 246.31
Log P RDKit 2.8
Topological polar surface area (Å2) RDKit 50.44
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 18
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.13
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.53
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
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 3
(8S,8aS)-8-hydroxy-3,5,8a-trimethyl-6,7,8,9-tetrahydrobenzo[f][1]benzofuran-4-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 0.765431
(8S,8aS)-8-hydroxy-3,5,8a-trimethyl-6,7,8,9-tetrahydrobenzo[f][1]benzofuran-4-one
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.37
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes