IMPPAT Phytochemical information: 
[(E,2S,3R,5S)-3,5-diacetyloxy-7-[(2R)-6-oxo-2,3-dihydropyran-2-yl]hept-6-en-2-yl] acetate
[(E,2S,3R,5S)-3,5-diacetyloxy-7-[(2R)-6-oxo-2,3-dihydropyran-2-yl]hept-6-en-2-yl] acetate
Summary

SMILES: CC(=O)O[C@@H](C[C@H]([C@@H](OC(=O)C)C)OC(=O)C)/C=C/[C@H]1CC=CC(=O)O1
InChI: InChI=1S/C18H24O8/c1-11(23-12(2)19)17(25-14(4)21)10-16(24-13(3)20)9-8-15-6-5-7-18(22)26-15/h5,7-9,11,15-17H,6,10H2,1-4H3/b9-8+/t11-,15+,16+,17+/m0/s1
InChIKey: GDOLPJAUNWCIIU-FTNCYZKBSA-N
DeepSMILES: CC=O)O[C@@H]C[C@H][C@@H]OC=O)C)))C))OC=O)C)))))/C=C/[C@H]CC=CC=O)O6
Scaffold Graph/Node/Bond level: O=C1C=CCCO1
Scaffold Graph/Node level: OC1CCCCO1
Scaffold Graph level: CC1CCCCC1
Functional groups: CC(=O)OC; C/C=C/C; O=C1C=CCCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Tetracarboxylic acids and derivatives
Synonymous chemical names:
hyptolide
External chemical identifiers:
CID:CID_101228910
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(E,2S,3R,5S)-3,5-diacetyloxy-7-[(2R)-6-oxo-2,3-dihydropyran-2-yl]hept-6-en-2-yl] acetate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 368.38
Log P RDKit 1.62
Topological polar surface area (Å2) RDKit 105.2
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.22
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.56
Number of rotatable bonds RDKit 11
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 1
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 1
[(E,2S,3R,5S)-3,5-diacetyloxy-7-[(2R)-6-oxo-2,3-dihydropyran-2-yl]hept-6-en-2-yl] acetate
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Bad
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.36
[(E,2S,3R,5S)-3,5-diacetyloxy-7-[(2R)-6-oxo-2,3-dihydropyran-2-yl]hept-6-en-2-yl] acetate
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 -7.42
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No