IMPPAT Phytochemical information: 
beta-D-Glucopyranoside, (3R,5S,5aS,6R,7S,8R,8aS)-hexahydro-8,8a-dihydroxy-7-((4-hydroxy-3-methoxybenzoyl)oxy)-3,6-methano-1H-cyclopenta(e)(1,3)dioxepin-5-yl

beta-D-Glucopyranoside, (3R,5S,5aS,6R,7S,8R,8aS)-hexahydro-8,8a-dihydroxy-7-((4-hydroxy-3-methoxybenzoyl)oxy)-3,6-methano-1H-cyclopenta(e)(1,3)dioxepin-5-yl
Summary

SMILES: OC[C@@H]1O[C@H](O[C@@H]2O[C@H]3OC[C@]4([C@@H]2[C@@H](C3)[C@@H]([C@H]4O)OC(=O)c2ccc(c(c2)OC)O)O)[C@H]([C@@H]([C@H]1O)O)O
InChI: InChI=1S/C23H30O14/c1-32-11-4-8(2-3-10(11)25)20(30)36-18-9-5-13-33-7-23(31,19(18)29)14(9)21(35-13)37-22-17(28)16(27)15(26)12(6-24)34-22/h2-4,9,12-19,21-22,24-29,31H,5-7H2,1H3/t9-,12+,13-,14-,15+,16-,17+,18+,19-,21+,22-,23-/m1/s1
InChIKey: DTNNYXMHYVWWHO-RYLNZNLUSA-N
DeepSMILES: OC[C@@H]O[C@H]O[C@@H]O[C@H]OC[C@][C@@H]7[C@@H]C7)[C@@H][C@H]5O))OC=O)cccccc6)OC)))O))))))))))O))))))))[C@H][C@@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C(OC1CC2COC3CC1C2C(OC1CCCCO1)O3)c1ccccc1
Scaffold Graph/Node level: OC(OC1CC2COC3CC1C2C(OC1CCCCO1)O3)C1CCCCC1
Scaffold Graph level: CC(CC1CC2CCC3CC(CC4CCCCC4)C2C1C3)C1CCCCC1
Functional groups: CO; CO[C@@H](C)O[C@H](C)O[C@H](C)OC; cC(=O)OC; cO; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Tannins
ClassyFire Subclass: Hydrolyzable tannins
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Monoterpenoids
NP Classifier Class: Iridoids monoterpenoids
Synonymous chemical names:
pikuroside
External chemical identifiers:
CID:132472101
Chemical structure download


beta-D-Glucopyranoside, (3R,5S,5aS,6R,7S,8R,8aS)-hexahydro-8,8a-dihydroxy-7-((4-hydroxy-3-methoxybenzoyl)oxy)-3,6-methano-1H-cyclopenta(e)(1,3)dioxepin-5-yl
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 530.48
Log P RDKit -2.82
Topological polar surface area (Å2) RDKit 214.06
Number of hydrogen bond acceptors RDKit 14
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 37
Number of heteroatoms RDKit 14
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 12
Stereochemical complexity RDKit 0.52
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 16
Shape complexity RDKit 0.7
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6


beta-D-Glucopyranoside, (3R,5S,5aS,6R,7S,8R,8aS)-hexahydro-8,8a-dihydroxy-7-((4-hydroxy-3-methoxybenzoyl)oxy)-3,6-methano-1H-cyclopenta(e)(1,3)dioxepin-5-yl
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
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 0.1849


beta-D-Glucopyranoside, (3R,5S,5aS,6R,7S,8R,8aS)-hexahydro-8,8a-dihydroxy-7-((4-hydroxy-3-methoxybenzoyl)oxy)-3,6-methano-1H-cyclopenta(e)(1,3)dioxepin-5-yl
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.96
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 0.0
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