IMPPAT Phytochemical information: 
(1R,2S,5S,6S,9S,10R)-5,9,10-trimethyl-3-oxatetracyclo[7.4.0.01,10.02,6]tridec-12-ene-4,11-dione
(1R,2S,5S,6S,9S,10R)-5,9,10-trimethyl-3-oxatetracyclo[7.4.0.01,10.02,6]tridec-12-ene-4,11-dione
Summary

SMILES: C[C@@H]1C(=O)O[C@H]2[C@H]1CC[C@]1([C@]32C=CC(=O)[C@]13C)C
InChI: InChI=1S/C15H18O3/c1-8-9-4-6-13(2)14(3)10(16)5-7-15(13,14)11(9)18-12(8)17/h5,7-9,11H,4,6H2,1-3H3/t8-,9-,11-,13+,14+,15+/m0/s1
InChIKey: DAGAGXCQQYCLAE-DZOXWOQYSA-N
DeepSMILES: C[C@@H]C=O)O[C@H][C@H]5CC[C@][C@@]6C=CC=O)[C@]65C))))))C
Scaffold Graph/Node/Bond level: O=C1CC2CCC3C4C(=O)C=CC34C2O1
Scaffold Graph/Node level: OC1CC2CCC3C4C(O)CCC34C2O1
Scaffold Graph level: CC1CC2CCC3C4C(C)CCC34C2C1
Functional groups: COC(=O)C; O=C1C=CCC1
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:
lumisantonin
External chemical identifiers:
CID:CID_101596929
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1R,2S,5S,6S,9S,10R)-5,9,10-trimethyl-3-oxatetracyclo[7.4.0.01,10.02,6]tridec-12-ene-4,11-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 246.31
Log P RDKit 2.11
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 3
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
(1R,2S,5S,6S,9S,10R)-5,9,10-trimethyl-3-oxatetracyclo[7.4.0.01,10.02,6]tridec-12-ene-4,11-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 0.614771
(1R,2S,5S,6S,9S,10R)-5,9,10-trimethyl-3-oxatetracyclo[7.4.0.01,10.02,6]tridec-12-ene-4,11-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 -6.16
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