IMPPAT Phytochemical information: 
1alpha-(beta-D-Glucopyranosyloxy)-7-[(4-hydroxybenzoyl)oxymethyl]-3beta-methoxy-1,3,4,4aalpha,5,7aalpha-hexahydrocyclopenta[c]pyran-5alpha-ol
1alpha-(beta-D-Glucopyranosyloxy)-7-[(4-hydroxybenzoyl)oxymethyl]-3beta-methoxy-1,3,4,4aalpha,5,7aalpha-hexahydrocyclopenta[c]pyran-5alpha-ol
Summary

SMILES: CO[C@@H]1O[C@@H](O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)[C@H]2[C@@H](C1)[C@H](O)C=C2COC(=O)c1ccc(cc1)O
InChI: InChI=1S/C23H30O12/c1-31-16-7-13-14(26)6-11(9-32-21(30)10-2-4-12(25)5-3-10)17(13)22(34-16)35-23-20(29)19(28)18(27)15(8-24)33-23/h2-6,13-20,22-29H,7-9H2,1H3/t13-,14+,15+,16+,17+,18+,19-,20+,22-,23-/m0/s1
InChIKey: RPIYNUXBYSWXNA-TXNASDCWSA-N
DeepSMILES: CO[C@@H]O[C@@H]O[C@@H]O[C@H]CO))[C@H][C@@H][C@H]6O))O))O))))))[C@H][C@@H]C6)[C@H]O)C=C5COC=O)cccccc6))O
Scaffold Graph/Node/Bond level: O=C(OCC1=CCC2CCOC(OC3CCCCO3)C12)c1ccccc1
Scaffold Graph/Node level: OC(OCC1CCC2CCOC(OC3CCCCO3)C21)C1CCCCC1
Scaffold Graph level: CC(CCC1CCC2CCCC(CC3CCCCC3)C21)C1CCCCC1
Functional groups: CO[C@@H](C)O[C@@H](O[C@@H](C)OC)C; cO; CO; CC(=CC)C; cC(=O)OC
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:
nishindaside
External chemical identifiers:
CID:CID_21724410; ZINC:ZINC000100735762; SureChEMBL:SCHEMBL382085
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
1alpha-(beta-D-Glucopyranosyloxy)-7-[(4-hydroxybenzoyl)oxymethyl]-3beta-methoxy-1,3,4,4aalpha,5,7aalpha-hexahydrocyclopenta[c]pyran-5alpha-ol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 498.48
Log P RDKit -1.38
Topological polar surface area (Å2) RDKit 184.6
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 35
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.43
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.61
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 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
1alpha-(beta-D-Glucopyranosyloxy)-7-[(4-hydroxybenzoyl)oxymethyl]-3beta-methoxy-1,3,4,4aalpha,5,7aalpha-hexahydrocyclopenta[c]pyran-5alpha-ol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 2
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.19
1alpha-(beta-D-Glucopyranosyloxy)-7-[(4-hydroxybenzoyl)oxymethyl]-3beta-methoxy-1,3,4,4aalpha,5,7aalpha-hexahydrocyclopenta[c]pyran-5alpha-ol
ADME 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 -10.24
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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