IMPPAT Phytochemical information: 
Proanthocyanidin A2
Proanthocyanidin A2
Summary

SMILES: Oc1cc(O)c2c(c1)O[C@@]1([C@@H]([C@H]2c2c(O1)cc(c1c2O[C@@H]([C@@H](C1)O)c1ccc(c(c1)O)O)O)O)c1ccc(c(c1)O)O
InChI: InChI=1S/C30H24O12/c31-13-7-20(37)24-22(8-13)41-30(12-2-4-16(33)19(36)6-12)29(39)26(24)25-23(42-30)10-17(34)14-9-21(38)27(40-28(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,21,26-27,29,31-39H,9H2/t21-,26-,27-,29-,30+/m1/s1
InChIKey: NSEWTSAADLNHNH-LSBOWGMISA-N
DeepSMILES: OcccO)ccc6)O[C@@][C@@H][C@H]6ccO6)cccc6O[C@@H][C@@H]C6)O))cccccc6)O))O)))))))))O))))))O))cccccc6)O))O
Scaffold Graph/Node/Bond level: c1ccc(C2CCc3ccc4c(c3O2)C2CC(c3ccccc3)(Oc3ccccc32)O4)cc1
Scaffold Graph/Node level: C1CCC(C2CCC3CCC4OC5(C6CCCCC6)CC(C6CCCCC6O5)C4C3O2)CC1
Scaffold Graph level: C1CCC(C2CCC3CCC4CC5(C6CCCCC6)CC6CCCCC6C(C5)C4C3C2)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:
proanthocyanidin a-2, procyanidin a2, proanthocyanidin a₂
External chemical identifiers:
CID:CID_124025; ChEMBL:CHEMBL286933; ChEBI:CHEBI:28472; ZINC:ZINC000004098619; FDASRS:UQN6668Q4R; SureChEMBL:SCHEMBL981582; MolPort-046-426-712
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Proanthocyanidin A2
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 A2
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 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 0.15781
Proanthocyanidin A2
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 -8.12
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No