IMPPAT Phytochemical information: 
(1alpha,2beta,5alpha,8alpha,10alpha)-1,10-Epoxy-2-hydroxy-3,7(11)-guaiadien-12,8-olide
(1alpha,2beta,5alpha,8alpha,10alpha)-1,10-Epoxy-2-hydroxy-3,7(11)-guaiadien-12,8-olide
Summary

SMILES: CC1=C2C[C@H]3C(=C[C@H]([C@]43[C@@](C[C@@H]2OC1=O)(O4)C)O)C
InChI: InChI=1S/C15H18O4/c1-7-4-12(16)15-10(7)5-9-8(2)13(17)18-11(9)6-14(15,3)19-15/h4,10-12,16H,5-6H2,1-3H3/t10-,11-,12+,14+,15+/m0/s1
InChIKey: QKIQAUSGMKJYFS-CWFCOSEVSA-N
DeepSMILES: CC=CC[C@H]C=C[C@H][C@@]5[C@@]C[C@@H]%10OC%13=O)))))O3)C)))O)))C
Scaffold Graph/Node/Bond level: O=C1C=C2CC3C=CCC34OC4CC2O1
Scaffold Graph/Node level: OC1CC2CC3CCCC34OC4CC2O1
Scaffold Graph level: CC1CC2CC3CCCC34CC4CC2C1
Functional groups: CC1=C(C)C(=O)OC1; CC(=CC)C; C[C@]1(C)O[C@]1(C)C; CO
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:
(1alpha,2beta,5alpha,8alpha,10alpha)-1,10-epoxy-2-hydroxy-3,7(11)-guaiadien-12,8-olide
External chemical identifiers:
CID:CID_11299991; ChEMBL:CHEMBL501119; ZINC:ZINC000034456757
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1alpha,2beta,5alpha,8alpha,10alpha)-1,10-Epoxy-2-hydroxy-3,7(11)-guaiadien-12,8-olide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 262.31
Log P RDKit 1.49
Topological polar surface area (Å2) RDKit 59.06
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
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 5
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.67
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 2
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 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
(1alpha,2beta,5alpha,8alpha,10alpha)-1,10-Epoxy-2-hydroxy-3,7(11)-guaiadien-12,8-olide
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 0.40801
(1alpha,2beta,5alpha,8alpha,10alpha)-1,10-Epoxy-2-hydroxy-3,7(11)-guaiadien-12,8-olide
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.84
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 Yes