IMPPAT Phytochemical information: 
[(1S,4aR,5S,7aS)-5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
[(1S,4aR,5S,7aS)-5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@H]3[C@H]2C(=C[C@H]3O)COC(=O)/C=C/c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C24H28O11/c25-10-17-20(29)21(30)22(31)24(34-17)35-23-19-13(9-16(27)15(19)7-8-32-23)11-33-18(28)6-3-12-1-4-14(26)5-2-12/h1-9,15-17,19-27,29-31H,10-11H2/b6-3+/t15-,16+,17+,19+,20+,21-,22+,23-,24-/m0/s1
InChIKey: DQTBTFHCLVMGBP-WXUDOLSOSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@@H]OC=C[C@@H][C@H]6C=C[C@H]5O)))COC=O)/C=C/cccccc6))O))))))))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OCC1=CCC2C=COC(OC3CCCCO3)C12
Scaffold Graph/Node level: OC(CCC1CCCCC1)OCC1CCC2CCOC(OC3CCCCO3)C21
Scaffold Graph level: CC(CCC1CCCCC1)CCC1CCC2CCCC(CC3CCCCC3)C21
Functional groups: CO; CO[C@@H](O[C@H]1CCC=CO1)C; CC(=CC)C; c/C=C/C(=O)OC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene glycosides
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Monoterpenoids
NP Classifier Class: Iridoids monoterpenoids
Synonymous chemical names:
eurostoside
External chemical identifiers:
CID:CID_20839507; ChEMBL:CHEMBL1080020; ZINC:ZINC000049775277; MolPort-005-944-661
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(1S,4aR,5S,7aS)-5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 492.48
Log P RDKit -0.83
Topological polar surface area (Å2) RDKit 175.37
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 35
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.38
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.46
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
[(1S,4aR,5S,7aS)-5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 2
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.159136
[(1S,4aR,5S,7aS)-5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.82
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