IMPPAT Phytochemical information: 
petunidin-3-O-(6-O-cis-p-coumaryl-beta-D-glucoside)
petunidin-3-O-(6-O-cis-p-coumaryl-beta-D-glucoside)
Summary

SMILES: COc1cc(cc(c1O)O)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/C31H28O14/c1-41-22-9-15(8-20(35)26(22)37)30-23(12-18-19(34)10-17(33)11-21(18)43-30)44-31-29(40)28(39)27(38)24(45-31)13-42-25(36)7-4-14-2-5-16(32)6-3-14/h2-12,24,27-29,31,38-40H,13H2,1H3,(H4-,32,33,34,35,36,37)/p+1/t24-,27-,28+,29-,31-/m1/s1
InChIKey: KTFQEFWNLAUGAX-VEZAKBLNSA-O
DeepSMILES: COcccccc6O))O)))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:
petunidin 3-o-(6-o-p-coumaroyl)glucoside
External chemical identifiers:
CID:CID_72193655; ChEBI:CHEBI:75709; ZINC:ZINC000096015187
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
petunidin-3-O-(6-O-cis-p-coumaryl-beta-D-glucoside)
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 625.56
Log P RDKit 2.36
Topological polar surface area (Å2) RDKit 227.13
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 31
Number of heavy atoms RDKit 45
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 7
Shape complexity RDKit 0.23
Number of rotatable bonds RDKit 9
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
petunidin-3-O-(6-O-cis-p-coumaryl-beta-D-glucoside)
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 3
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 0.0608807
petunidin-3-O-(6-O-cis-p-coumaryl-beta-D-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 -8.80
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