IMPPAT Phytochemical information: 
Proanthocyanidin A-6
Proanthocyanidin A-6
Summary

SMILES: Oc1cc(O)c2c(c1)O[C@@]1([C@@H]([C@H]2c2c(O1)cc1c(c2O)C[C@H]([C@H](O1)c1ccc(c(c1)O)O)O)O)c1ccc(c(c1)O)O
InChI: InChI=1S/C30H24O12/c31-13-7-19(36)24-22(8-13)41-30(12-2-4-16(33)18(35)6-12)29(39)26(24)25-23(42-30)10-21-14(27(25)38)9-20(37)28(40-21)11-1-3-15(32)17(34)5-11/h1-8,10,20,26,28-29,31-39H,9H2/t20-,26-,28-,29-,30+/m1/s1
InChIKey: BEPYKTSNKZMROV-FEEPWOQDSA-N
DeepSMILES: OcccO)ccc6)O[C@@][C@@H][C@H]6ccO6)cccc6O))C[C@H][C@H]O6)cccccc6)O))O))))))O)))))))))O))cccccc6)O))O
Scaffold Graph/Node/Bond level: c1ccc(C2CCc3cc4c(cc3O2)OC2(c3ccccc3)CC4c3ccccc3O2)cc1
Scaffold Graph/Node level: C1CCC(C2CCC3CC4C(CC3O2)OC2(C3CCCCC3)CC4C3CCCCC3O2)CC1
Scaffold Graph level: C1CCC(C2CCC3CC4C(CC3C2)CC2(C3CCCCC3)CC3CCCCC3C4C2)CC1
Functional groups: cO; CO; cO[C@](c)(C)Oc; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Biflavonoids and polyflavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Proanthocyanins
Synonymous chemical names:
3-o-(4-hydroxybenzoyl)-(2r,3r)-3,3,4,5,7-pentahydroxyflavan
External chemical identifiers:
CID:CID_45359583; ZINC:ZINC000067903315
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Proanthocyanidin A-6
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 576.51
Log P RDKit 2.79
Topological polar surface area (Å2) RDKit 209.76
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 9
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 42
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.17
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 24
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.2
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 4
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Proanthocyanidin A-6
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 2
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 0.16
Proanthocyanidin A-6
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.87
Number of PAINS structural alerts SwissADME 1
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 Yes
P-glycoprotein substrate SwissADME No