IMPPAT Phytochemical information: 
(3R,3aR,5aR,9bS)-3a-hydroxy-3-(hydroxymethyl)-5a,9-dimethyl-4,5,6,7,8,9b-hexahydro-3H-benzo[g][1]benzofuran-2-one
(3R,3aR,5aR,9bS)-3a-hydroxy-3-(hydroxymethyl)-5a,9-dimethyl-4,5,6,7,8,9b-hexahydro-3H-benzo[g][1]benzofuran-2-one
Summary

SMILES: OC[C@H]1C(=O)O[C@@H]2[C@@]1(O)CC[C@@]1(C2=C(C)CCC1)C
InChI: InChI=1S/C15H22O4/c1-9-4-3-5-14(2)6-7-15(18)10(8-16)13(17)19-12(15)11(9)14/h10,12,16,18H,3-8H2,1-2H3/t10-,12-,14+,15+/m0/s1
InChIKey: MZLCLGJDVOQTRG-OBCWZRDOSA-N
DeepSMILES: OC[C@H]C=O)O[C@@H][C@@]5O)CC[C@@]C6=CC)CCC6)))))C
Scaffold Graph/Node/Bond level: O=C1CC2CCC3CCCC=C3C2O1
Scaffold Graph/Node level: OC1CC2CCC3CCCCC3C2O1
Scaffold Graph level: CC1CC2CCC3CCCCC3C2C1
Functional groups: CO; COC(=O)C; CC(=C(C)C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene lactones
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Eudesmane sesquiterpenoids
Synonymous chemical names:
11alpha,13-dihydro-7alpha,13-dihydroxyfrullanolide
External chemical identifiers:
CID:CID_56941573
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(3R,3aR,5aR,9bS)-3a-hydroxy-3-(hydroxymethyl)-5a,9-dimethyl-4,5,6,7,8,9b-hexahydro-3H-benzo[g][1]benzofuran-2-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 266.34
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 15
Number of heavy atoms RDKit 19
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 0.27
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.8
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
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 3
(3R,3aR,5aR,9bS)-3a-hydroxy-3-(hydroxymethyl)-5a,9-dimethyl-4,5,6,7,8,9b-hexahydro-3H-benzo[g][1]benzofuran-2-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.56
(3R,3aR,5aR,9bS)-3a-hydroxy-3-(hydroxymethyl)-5a,9-dimethyl-4,5,6,7,8,9b-hexahydro-3H-benzo[g][1]benzofuran-2-one
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 -7.01
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 Yes