IMPPAT Phytochemical information: 
(1aR,3S,4E,5aR,8aR,9R,10aR)-3-hydroxy-4,10a-dimethyl-8-methylidene-7-oxo-1a,2,3,5a,7,8,8a,9,10,10a-decahydrooxireno[5,6]cyclodeca[1,2-b]furan-9-yl (2E)-2-methylbut-2-enoate
(1aR,3S,4E,5aR,8aR,9R,10aR)-3-hydroxy-4,10a-dimethyl-8-methylidene-7-oxo-1a,2,3,5a,7,8,8a,9,10,10a-decahydrooxireno[5,6]cyclodeca[1,2-b]furan-9-yl (2E)-2-methylbut-2-enoate
Summary

SMILES: C/C=C(/C(=O)O[C@@H]1C[C@@]2(C)O[C@@H]2C[C@@H](/C(=C/[C@@H]2[C@@H]1C(=C)C(=O)O2)/C)O)\C
InChI: InChI=1S/C20H26O6/c1-6-10(2)18(22)25-15-9-20(5)16(26-20)8-13(21)11(3)7-14-17(15)12(4)19(23)24-14/h6-7,13-17,21H,4,8-9H2,1-3,5H3/b10-6+,11-7+/t13-,14+,15+,16+,17-,20+/m0/s1
InChIKey: DZTWAOVNNLDWNH-XYXZLXRDSA-N
DeepSMILES: C/C=C/C=O)O[C@@H]C[C@@]C)O[C@@H]3C[C@@H]/C=C/[C@@H][C@@H]%11C=C)C=O)O5))))))/C))O))))))))))\C
Scaffold Graph/Node/Bond level: C=C1C(=O)OC2C=CCCC3OC3CCC12
Scaffold Graph/Node level: CC1C(O)OC2CCCCC3OC3CCC21
Scaffold Graph level: CC1CC2CCCCC3CC3CCC2C1C
Functional groups: C/C=C(\C)C(=O)OC; C[C@H]1O[C@]1(C)C; C/C(=C\C)C; C=C1CCOC1=O; 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: Germacrane sesquiterpenoids
Synonymous chemical names:
heliangin, Helianginc, Heliangin
External chemical identifiers:
CID:CID_70697714; ChEBI:CHEBI:5638
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1aR,3S,4E,5aR,8aR,9R,10aR)-3-hydroxy-4,10a-dimethyl-8-methylidene-7-oxo-1a,2,3,5a,7,8,8a,9,10,10a-decahydrooxireno[5,6]cyclodeca[1,2-b]furan-9-yl (2E)-2-methylbut-2-enoate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 362.42
Log P RDKit 2.22
Topological polar surface area (Å2) RDKit 85.36
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.3
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.6
Number of rotatable bonds RDKit 3
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 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
(1aR,3S,4E,5aR,8aR,9R,10aR)-3-hydroxy-4,10a-dimethyl-8-methylidene-7-oxo-1a,2,3,5a,7,8,8a,9,10,10a-decahydrooxireno[5,6]cyclodeca[1,2-b]furan-9-yl (2E)-2-methylbut-2-enoate
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.350862
(1aR,3S,4E,5aR,8aR,9R,10aR)-3-hydroxy-4,10a-dimethyl-8-methylidene-7-oxo-1a,2,3,5a,7,8,8a,9,10,10a-decahydrooxireno[5,6]cyclodeca[1,2-b]furan-9-yl (2E)-2-methylbut-2-enoate
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.18
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 4
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