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

SMILES: OC[C@H]1O[C@@H](Oc2cc3c(O)cc(cc3[o+]c2c2ccc(c(c2)OC)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C22H22O11/c1-30-15-4-9(2-3-12(15)25)21-16(7-11-13(26)5-10(24)6-14(11)31-21)32-22-20(29)19(28)18(27)17(8-23)33-22/h2-7,17-20,22-23,27-29H,8H2,1H3,(H2-,24,25,26)/p+1/t17-,18-,19+,20-,22-/m1/s1
InChIKey: ZZWPMFROUHHAKY-OUUKCGNVSA-O
DeepSMILES: OC[C@H]O[C@@H]OccccO)cccc6[o+]c%10cccccc6)OC)))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; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavonoid glycosides
Synonymous chemical names:
Peonidin-3-glucoside, peonidin-3-glucoside, 3-glucoside peonidin
External chemical identifiers:
CID:CID_443654; ChEMBL:CHEMBL1784263; ChEBI:CHEBI:74793; ZINC:ZINC000004102357
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Peonidin-3-glucoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 463.42
Log P RDKit 0.69
Topological polar surface area (Å2) RDKit 180.6
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 11
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
Peonidin-3-glucoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
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 0.264465
Peonidin-3-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 -8.80
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