IMPPAT Phytochemical information: 
[(1S,2R)-2-Acetyloxy-1-[(2R)-6-oxo-2,3-dihydropyran-2-yl]-2-phenylethyl] acetate
[(1S,2R)-2-Acetyloxy-1-[(2R)-6-oxo-2,3-dihydropyran-2-yl]-2-phenylethyl] acetate
Summary

SMILES: O=C1C=CC[C@@H](O1)[C@@H]([C@@H](c1ccccc1)OC(=O)C)OC(=O)C
InChI: InChI=1S/C17H18O6/c1-11(18)21-16(13-7-4-3-5-8-13)17(22-12(2)19)14-9-6-10-15(20)23-14/h3-8,10,14,16-17H,9H2,1-2H3/t14-,16-,17+/m1/s1
InChIKey: JJGQHRYXJBODPH-OIISXLGYSA-N
DeepSMILES: O=CC=CC[C@@H]O6)[C@@H][C@@H]cccccc6))))))OC=O)C))))OC=O)C
Scaffold Graph/Node/Bond level: O=C1C=CCC(CCc2ccccc2)O1
Scaffold Graph/Node level: OC1CCCC(CCC2CCCCC2)O1
Scaffold Graph level: CC1CCCC(CCC2CCCCC2)C1
Functional groups: O=C1C=CCCO1; CC(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Benzene and substituted derivatives
ClassyFire Subclass: Benzyloxycarbonyls
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Styrylpyrones
NP Classifier Class: Kavalactones and derivatives
Synonymous chemical names:
goniodiol diacetate
External chemical identifiers:
CID:CID_11012583; MolPort-046-153-758
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(1S,2R)-2-Acetyloxy-1-[(2R)-6-oxo-2,3-dihydropyran-2-yl]-2-phenylethyl] acetate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 318.33
Log P RDKit 2.09
Topological polar surface area (Å2) RDKit 78.9
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.35
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
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 2
[(1S,2R)-2-Acetyloxy-1-[(2R)-6-oxo-2,3-dihydropyran-2-yl]-2-phenylethyl] 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 Good
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 0.61
[(1S,2R)-2-Acetyloxy-1-[(2R)-6-oxo-2,3-dihydropyran-2-yl]-2-phenylethyl] 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 -6.74
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No