IMPPAT Phytochemical information: 
Cyanidin monoglucoside
Cyanidin monoglucoside
Summary

SMILES: OC[C@H]1O[C@@H](O)[C@@H]([C@H]([C@@H]1O)O)Oc1cc(O)c2c(c1)[o+]c(c(c2)O)c1ccc(c(c1)O)O.[Cl-]
InChI: InChI=1S/C21H20O11.ClH/c22-7-16-17(27)18(28)20(21(29)32-16)30-9-4-12(24)10-6-14(26)19(31-15(10)5-9)8-1-2-11(23)13(25)3-8;/h1-6,16-18,20-22,27-29H,7H2,(H3-,23,24,25,26);1H/t16-,17-,18+,20-,21-;/m1./s1
InChIKey: AOYDIFJAPBNESL-GIICXGHVSA-N
DeepSMILES: OC[C@H]O[C@@H]O)[C@@H][C@H][C@@H]6O))O))OcccO)ccc6)[o+]ccc6)O))cccccc6)O))O.[Cl-]
Scaffold Graph/Node/Bond level: c1ccc(-c2ccc3ccc(OC4CCCOC4)cc3[o+]2)cc1
Scaffold Graph/Node level: C1CCC(C2CCC3CCC(OC4CCCOC4)CC3O2)CC1
Scaffold Graph level: C1CCC(CC2CCC3CCC(C4CCCCC4)CC3C2)CC1
Functional groups: CO; [Cl-]; CO[C@@H](O)C; cOC; cO; c[o+]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Hydroxyflavonoids
Synonymous chemical names:
1-methoxybut-1-en-3-yne, cyanidin-monoglycoside
External chemical identifiers:
CID:CID_185664
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cyanidin monoglucoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 484.84
Log P RDKit -2.61
Topological polar surface area (Å2) RDKit 191.6
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 33
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 0.24
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
Cyanidin monoglucoside
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 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 0.14
Cyanidin monoglucoside
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 -9.42
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
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