IMPPAT Phytochemical information: 
3,6,9-Trimethyl-3,3a,4,5,6,6a,9a,9b-octahydroazuleno[4,5-b]furan-2,7-dione
3,6,9-Trimethyl-3,3a,4,5,6,6a,9a,9b-octahydroazuleno[4,5-b]furan-2,7-dione
Summary

SMILES: C[C@@H]1C(=O)OC2[C@H]1CCC(C1C2C(=CC1=O)C)C
InChI: InChI=1S/C15H20O3/c1-7-4-5-10-9(3)15(17)18-14(10)13-8(2)6-11(16)12(7)13/h6-7,9-10,12-14H,4-5H2,1-3H3/t7?,9-,10-,12?,13?,14?/m0/s1
InChIKey: FJKWKEZAHVWIOR-DLQYATBFSA-N
DeepSMILES: C[C@@H]C=O)OC[C@H]5CCCCC7C=CC5=O)))C))))C
Scaffold Graph/Node/Bond level: O=C1CC2CCCC3C(=O)C=CC3C2O1
Scaffold Graph/Node level: OC1CC2CCCC3C(O)CCC3C2O1
Scaffold Graph level: CC1CC2CCCC3C(C)CCC3C2C1
Functional groups: COC(=O)C; CC1=CC(=O)CC1
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: Guaiane sesquiterpenoids
Synonymous chemical names:
cichoralexin
External chemical identifiers:
CID:CID_183102
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
3,6,9-Trimethyl-3,3a,4,5,6,6a,9a,9b-octahydroazuleno[4,5-b]furan-2,7-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 248.32
Log P RDKit 2.36
Topological polar surface area (Å2) RDKit 43.37
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 0
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 6
Stereochemical complexity RDKit 0.4
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 4
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.73
Number of rotatable bonds RDKit 0
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
3,6,9-Trimethyl-3,3a,4,5,6,6a,9a,9b-octahydroazuleno[4,5-b]furan-2,7-dione
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 0.618014
3,6,9-Trimethyl-3,3a,4,5,6,6a,9a,9b-octahydroazuleno[4,5-b]furan-2,7-dione
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 -6.22
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 No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No