IMPPAT Phytochemical information: 
Auriculoside
Auriculoside
Summary

SMILES: OC[C@H]1O[C@@H](Oc2cc(cc(c2OC)O)[C@@H]2CCc3c(O2)cc(cc3)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C22H26O10/c1-29-21-13(25)6-11(14-5-3-10-2-4-12(24)8-15(10)30-14)7-16(21)31-22-20(28)19(27)18(26)17(9-23)32-22/h2,4,6-8,14,17-20,22-28H,3,5,9H2,1H3/t14-,17+,18+,19-,20+,22+/m0/s1
InChIKey: IJMWYFHXJWRHQH-PSWNVJQFSA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc6OC)))O)))[C@@H]CCccO6)cccc6))O))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: c1cc(OC2CCCCO2)cc(C2CCc3ccccc3O2)c1
Scaffold Graph/Node level: C1CCC(OC2CCCC(C3CCC4CCCCC4O3)C2)OC1
Scaffold Graph level: C1CCC(CC2CCCC(C3CCC4CCCCC4C3)C2)CC1
Functional groups: CO; cO[C@@H](C)OC; cOC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavonoid glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavans
Synonymous chemical names:
auriculoside
External chemical identifiers:
CID:CID_442260; ChEBI:CHEBI:2929; SureChEMBL:SCHEMBL4743855
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Auriculoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 450.44
Log P RDKit 0.35
Topological polar surface area (Å2) RDKit 158.3
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.27
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.45
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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
Auriculoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
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 Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.38
Auriculoside
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 Low
Log Kp (Skin permeation, cm/s) SwissADME -8.40
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 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 Yes