IMPPAT Phytochemical information: 
Proanthocyanidin
Proanthocyanidin
Summary

SMILES: COc1c(O)cc(cc1O)C1Oc2c(C[C@H]1O)c(O)cc(c2[C@@H]1[C@@H](O)[C@H](Oc2c1c(O)cc(c2)O)c1ccc(cc1)O)O
InChI: InChI=1S/C31H28O12/c1-41-31-20(37)6-13(7-21(31)38)28-22(39)10-16-17(34)11-19(36)25(30(16)43-28)26-24-18(35)8-15(33)9-23(24)42-29(27(26)40)12-2-4-14(32)5-3-12/h2-9,11,22,26-29,32-40H,10H2,1H3/t22-,26-,27-,28?,29-/m1/s1
InChIKey: JPFCOVZKLAXXOE-XBNSMERZSA-N
DeepSMILES: COccO)cccc6O)))COccC[C@H]6O)))cO)ccc6[C@@H][C@@H]O)[C@H]Occ6cO)ccc6)O)))))))cccccc6))O)))))))))O
Scaffold Graph/Node/Bond level: c1ccc(C2CC(c3cccc4c3OC(c3ccccc3)CC4)c3ccccc3O2)cc1
Scaffold Graph/Node level: C1CCC(C2CC(C3CCCC4CCC(C5CCCCC5)OC43)C3CCCCC3O2)CC1
Scaffold Graph level: C1CCC(C2CCC3CCCC(C4CC(C5CCCCC5)CC5CCCCC54)C3C2)CC1
Functional groups: cOC; cO; CO
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: Flavan-3-ols|Proanthocyanins
Synonymous chemical names:
Proanthocyanidin, proanthocyanidins, proanthocyandin, proanthocyanidin, proanthocyanidin-a-type
External chemical identifiers:
CID:CID_108065; SureChEMBL:SCHEMBL4747623
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Proanthocyanidin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 592.55
Log P RDKit 3.3
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 31
Number of heavy atoms RDKit 43
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 0.16
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 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 4
Total number of rings RDKit 6
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 6
Proanthocyanidin
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.17
Proanthocyanidin
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 -8.00
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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
Proanthocyanidin
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000356438PTGS2828
ENSP00000358223PNLIP823
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.