IMPPAT Phytochemical information: 
Pelargonidin 3-glucoside
Pelargonidin 3-glucoside
Summary

SMILES: OC[C@H]1O[C@@H](Oc2cc3c(O)cc(cc3[o+]c2c2ccc(cc2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C21H20O10/c22-8-16-17(26)18(27)19(28)21(31-16)30-15-7-12-13(25)5-11(24)6-14(12)29-20(15)9-1-3-10(23)4-2-9/h1-7,16-19,21-22,26-28H,8H2,(H2-,23,24,25)/p+1/t16-,17-,18+,19-,21-/m1/s1
InChIKey: ABVCUBUIXWJYSE-GQUPQBGVSA-O
DeepSMILES: OC[C@H]O[C@@H]OccccO)cccc6[o+]c%10cccccc6))O)))))))))O))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: c1ccc(-c2[o+]c3ccccc3cc2OC2CCCCO2)cc1
Scaffold Graph/Node level: C1CCC(C2OC3CCCCC3CC2OC2CCCCO2)CC1
Scaffold Graph level: C1CCC(CC2CC3CCCCC3CC2C2CCCCC2)CC1
Functional groups: CO; cO[C@@H](C)OC; cO; c[o+]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavonoid glycosides
Synonymous chemical names:
pelargonidin-3-o-glucoside, Pelargonidin-3-glucoside, pelargonidin 3-glucoside, pelargonidin-3-glucoside
External chemical identifiers:
CID:CID_443648; ChEBI:CHEBI:31967; ZINC:ZINC000004102353; FDASRS:W623YHH61A; SureChEMBL:SCHEMBL347415
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Pelargonidin 3-glucoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 433.39
Log P RDKit 0.68
Topological polar surface area (Å2) RDKit 171.37
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.24
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.29
Number of rotatable bonds RDKit 4
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
Pelargonidin 3-glucoside
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 0.29
Pelargonidin 3-glucoside
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 -8.60
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