IMPPAT Phytochemical information: 
3,5-di-O-(beta-Glucopyranosyl) pelargonidin 6''-O-4, 6'''-O-1-cyclic malate
3,5-di-O-(beta-Glucopyranosyl) pelargonidin 6''-O-4, 6'''-O-1-cyclic malate
Summary

SMILES: Oc1ccc(cc1)C1=C2O[C@@H]3O[C@H](COC(=O)CC(C(=O)OC[C@H]4OC(/[O+]=c/5\c(=C2)c(O1)cc(O)c5)[C@H](O)C([C@@H]4O)O)O)[C@H](C(C3O)O)O
InChI: InChI=1S/C31H32O18/c32-12-3-1-11(2-4-12)28-18-7-14-16(45-28)5-13(33)6-17(14)46-30-26(40)25(39)23(37)20(49-30)10-44-29(42)15(34)8-21(35)43-9-19-22(36)24(38)27(41)31(47-18)48-19/h1-7,15,19-20,22-27,30-31,34,36-41H,8-10H2,(H-,32,33)/p+1/t15?,19-,20-,22-,23-,24?,25?,26-,27?,30?,31-/m1/s1
InChIKey: MDSZBCFPVUABGB-SVUMSXGASA-O
DeepSMILES: Occcccc6))C=CO[C@@H]O[C@H]COC=O)CCC=O)OC[C@H]OC/[O+]=c\c=C%20)cO%22)ccO)c\6)))))))[C@H]O)C[C@@H]6O))O)))))))))O))))))[C@H]CC6O))O))O
Scaffold Graph/Node/Bond level: O=C1CCC(=O)OCC2CCCC(O2)[O+]=c2cccc3c2=CC(=C(c2ccccc2)O3)OC2CCCC(CO1)O2
Scaffold Graph/Node level: OC1CCC(O)OCC2CCCC(O2)OC2CC3C(CCCC3OC2C2CCCCC2)OC2CCCC(CO1)O2
Scaffold Graph level: CC1CCC(C)CCC2CCCC(C2)CC2CC3C(CCCC3CC2C2CCCCC2)CC2CCCC(CC1)C2
Functional groups: cO; cOC(c)=C(C)O[C@@H](C)OC; COC(=O)C; c=[O+]\C(C)OC; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Saccharolipids
Synonymous chemical names:
3,5-di-o-(beta-glucopyranosyl)-pelargonidin-6''-o-4,6'''-o-1-cyclic-malate
External chemical identifiers:
CID:CID_44256672
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
3,5-di-O-(beta-Glucopyranosyl) pelargonidin 6''-O-4, 6'''-O-1-cyclic malate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 693.59
Log P RDKit -4.26
Topological polar surface area (Å2) RDKit 282.89
Number of hydrogen bond acceptors RDKit 17
Number of hydrogen bond donors RDKit 9
Number of carbon atoms RDKit 31
Number of heavy atoms RDKit 49
Number of heteroatoms RDKit 18
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.35
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.45
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
3,5-di-O-(beta-Glucopyranosyl) pelargonidin 6''-O-4, 6'''-O-1-cyclic malate
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 4
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 0.10096
3,5-di-O-(beta-Glucopyranosyl) pelargonidin 6''-O-4, 6'''-O-1-cyclic malate
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 -13.05
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 Yes