IMPPAT Phytochemical information: 
Malvidin-3-O-(6-p-coumaroyl)glucoside
Malvidin-3-O-(6-p-coumaroyl)glucoside
Summary

SMILES: COc1cc(cc(c1O)OC)c1[o+]c2cc(O)cc(c2cc1O[C@H]1O[C@@H](COC(=O)/C=C/c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O)O
InChI: InChI=1S/C32H30O14/c1-41-22-9-16(10-23(42-2)27(22)37)31-24(13-19-20(35)11-18(34)12-21(19)44-31)45-32-30(40)29(39)28(38)25(46-32)14-43-26(36)8-5-15-3-6-17(33)7-4-15/h3-13,25,28-30,32,38-40H,14H2,1-2H3,(H3-,33,34,35,36,37)/p+1/t25-,28-,29+,30-,32-/m0/s1
InChIKey: HXQOVGDXCHFLOP-VNAFEJHWSA-O
DeepSMILES: COcccccc6O))OC))))c[o+]cccO)ccc6cc%10O[C@H]O[C@@H]COC=O)/C=C/cccccc6))O))))))))))[C@@H][C@H][C@@H]6O))O))O)))))))))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OCC1CCCC(Oc2cc3ccccc3[o+]c2-c2ccccc2)O1
Scaffold Graph/Node level: OC(CCC1CCCCC1)OCC1CCCC(OC2CC3CCCCC3OC2C2CCCCC2)O1
Scaffold Graph level: CC(CCC1CCCCC1)CCC1CCCC(CC2CC3CCCCC3CC2C2CCCCC2)C1
Functional groups: cOC; cO; CO; c[o+]c; cO[C@H](C)OC; c/C=C/C(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavonoid glycosides
Synonymous chemical names:
malvidin 3-o-(6-o-p-coumaroyl)glucoside
External chemical identifiers:
CID:CID_71308234
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Malvidin-3-O-(6-p-coumaroyl)glucoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 639.59
Log P RDKit 2.66
Topological polar surface area (Å2) RDKit 216.13
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 32
Number of heavy atoms RDKit 46
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 0.16
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 24
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.25
Number of rotatable bonds RDKit 10
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 4
Total number of rings RDKit 5
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 5
Malvidin-3-O-(6-p-coumaroyl)glucoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 3
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 0.08
Malvidin-3-O-(6-p-coumaroyl)glucoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.65
Number of PAINS structural alerts SwissADME 0
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