IMPPAT Phytochemical information: 
isorhamnetin-3-O-glucoside
isorhamnetin-3-O-glucoside
Summary

SMILES: OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C22H22O12/c1-31-12-4-8(2-3-10(12)25)20-21(17(28)15-11(26)5-9(24)6-13(15)32-20)34-22-19(30)18(29)16(27)14(7-23)33-22/h2-6,14,16,18-19,22-27,29-30H,7H2,1H3/t14-,16-,18+,19-,22+/m1/s1
InChIKey: CQLRUIIRRZYHHS-LFXZADKFSA-N
DeepSMILES: OC[C@H]O[C@@H]Occoccc6=O))cO)ccc6)O)))))))cccccc6)OC)))O))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1c(OC2CCCCO2)c(-c2ccccc2)oc2ccccc12
Scaffold Graph/Node level: OC1C2CCCCC2OC(C2CCCCC2)C1OC1CCCCO1
Scaffold Graph level: CC1C2CCCCC2CC(C2CCCCC2)C1CC1CCCCC1
Functional groups: CO; cO[C@@H](C)OC; coc; c=O; cO; cOC
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: Flavonols
Synonymous chemical names:
3-o-beta-d-glucoside-isorhamnetin, isorhamnetin 3-o-glucoside, isorhamnetin-3-o-beta-d-glucoside, isorhamnetin-3-o-glucoside, isorhamnetin-3-o-rhamnoglucoside, isorhamnetin-3-o-beta-glucoside, Isorhamnetin-3-O-glucoside
External chemical identifiers:
CID:CID_5318645; ChEMBL:CHEMBL234316; ChEBI:CHEBI:75750; ZINC:ZINC000004349394; FDASRS:BI252A6EPL; SureChEMBL:SCHEMBL2025447; MolPort-039-052-283
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
isorhamnetin-3-O-glucoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 478.41
Log P RDKit -0.24
Topological polar surface area (Å2) RDKit 199.51
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.23
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.32
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
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
isorhamnetin-3-O-glucoside
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 0
Ghose filter RDKit Passed
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 0.254313
isorhamnetin-3-O-glucoside
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 -8.73
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