IMPPAT Phytochemical information: 
Malvidin 3-arabinoside
Malvidin 3-arabinoside
Summary

SMILES: COc1cc(cc(c1O)OC)c1[o+]c2cc(O)cc(c2cc1O[C@@H]1OC[C@@H]([C@@H]([C@H]1O)O)O)O.[Cl-]
InChI: InChI=1S/C22H22O11.ClH/c1-29-15-3-9(4-16(30-2)19(15)27)21-17(33-22-20(28)18(26)13(25)8-31-22)7-11-12(24)5-10(23)6-14(11)32-21;/h3-7,13,18,20,22,25-26,28H,8H2,1-2H3,(H2-,23,24,27);1H/t13-,18-,20+,22-;/m0./s1
InChIKey: FXWDXPVECLXGRZ-XIGYXKQDSA-N
DeepSMILES: COcccccc6O))OC))))c[o+]cccO)ccc6cc%10O[C@@H]OC[C@@H][C@@H][C@H]6O))O))O)))))))))O.[Cl-]
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; cOC; [Cl-]; c[o+]c; cO[C@@H](C)OC; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavonoid glycosides
Synonymous chemical names:
Malvidin 3-arabinoside, malvidin-3-arabinoside, malvidin 3-arabinoside
External chemical identifiers:
CID:CID_91810654; FDASRS:P80A93IF7N; MolPort-039-338-984
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Malvidin 3-arabinoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 498.87
Log P RDKit -1.66
Topological polar surface area (Å2) RDKit 169.6
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 6
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 4
Stereochemical complexity RDKit 0.18
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
Malvidin 3-arabinoside
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 2
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 0.222421
Malvidin 3-arabinoside
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 -8.42
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