IMPPAT Phytochemical information: 
Cyanidin 3-malonylglucoside
Cyanidin 3-malonylglucoside
Summary

SMILES: OC(=O)CC(=O)OCC1OC(Oc2cc3c(O)cc(cc3[o+]c2c2ccc(c(c2)O)O)O)C(C(C1O)O)O
InChI: InChI=1S/C24H22O14/c25-10-4-13(27)11-6-16(23(36-15(11)5-10)9-1-2-12(26)14(28)3-9)37-24-22(34)21(33)20(32)17(38-24)8-35-19(31)7-18(29)30/h1-6,17,20-22,24,32-34H,7-8H2,(H4-,25,26,27,28,29,30)/p+1
InChIKey: ROQLTZUOXIQBDO-UHFFFAOYSA-O
DeepSMILES: OC=O)CC=O)OCCOCOccccO)cccc6[o+]c%10cccccc6)O))O)))))))))O))))))))CCC6O))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: CC(=O)O; CO; COC(C)=O; cOC(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:
cyanidin-3-malonylglucoside, Cyanidin-3-malonylglucoside
External chemical identifiers:
CID:CID_10143380
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cyanidin 3-malonylglucoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 535.43
Log P RDKit 0.41
Topological polar surface area (Å2) RDKit 234.97
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 38
Number of heteroatoms RDKit 14
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.21
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.29
Number of rotatable bonds RDKit 8
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 3-malonylglucoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
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 0.0885455
Cyanidin 3-malonylglucoside
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 -9.67
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 3
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