IMPPAT Phytochemical information: 
(1R,2R,6S,9S,10S)-1,9-dimethyl-5-methylidene-3,14-dioxatricyclo[8.4.0.02,6]tetradecane-4,13-dione
(1R,2R,6S,9S,10S)-1,9-dimethyl-5-methylidene-3,14-dioxatricyclo[8.4.0.02,6]tetradecane-4,13-dione
Summary

SMILES: O=C1CC[C@@H]2[C@](O1)(C)[C@@H]1OC(=O)C(=C)[C@@H]1CC[C@@H]2C
InChI: InChI=1S/C15H20O4/c1-8-4-5-10-9(2)14(17)18-13(10)15(3)11(8)6-7-12(16)19-15/h8,10-11,13H,2,4-7H2,1,3H3/t8-,10-,11-,13+,15+/m0/s1
InChIKey: FZYIWDQVFMUXPW-OEAYZANCSA-N
DeepSMILES: O=CCC[C@@H][C@]O6)C)[C@@H]OC=O)C=C)[C@@H]5CC[C@@H]%10C
Scaffold Graph/Node/Bond level: C=C1C(=O)OC2C1CCCC1CCC(=O)OC12
Scaffold Graph/Node level: CC1C(O)OC2C1CCCC1CCC(O)OC12
Scaffold Graph level: CC1CCC2CCCC3C(C)C(C)CC3C2C1
Functional groups: CC(=O)OC; C=C1CCOC1=O
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:
psilostachyin c
External chemical identifiers:
CID:CID_5320769; ZINC:ZINC000033833415
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1R,2R,6S,9S,10S)-1,9-dimethyl-5-methylidene-3,14-dioxatricyclo[8.4.0.02,6]tetradecane-4,13-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 264.32
Log P RDKit 2.23
Topological polar surface area (Å2) RDKit 52.6
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
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 5
Stereochemical complexity RDKit 0.33
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 1
Number of aliphatic heterocycles RDKit 2
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 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
(1R,2R,6S,9S,10S)-1,9-dimethyl-5-methylidene-3,14-dioxatricyclo[8.4.0.02,6]tetradecane-4,13-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 0.497078
(1R,2R,6S,9S,10S)-1,9-dimethyl-5-methylidene-3,14-dioxatricyclo[8.4.0.02,6]tetradecane-4,13-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 -6.11
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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