IMPPAT Phytochemical information: 
3,3'-Digalloylprocyanidin B2
3,3'-Digalloylprocyanidin B2
Summary

SMILES: Oc1cc(O)c2c(c1)O[C@@H]([C@@H]([C@H]2c1c(O)cc(c2c1O[C@@H]([C@@H](C2)OC(=O)c1cc(O)c(c(c1)O)O)c1ccc(c(c1)O)O)O)OC(=O)c1cc(O)c(c(c1)O)O)c1ccc(c(c1)O)O
InChI: InChI=1S/C44H34O20/c45-19-11-26(51)34-32(12-19)61-40(16-2-4-22(47)25(50)6-16)42(64-44(60)18-9-30(55)38(58)31(56)10-18)36(34)35-27(52)14-23(48)20-13-33(62-43(59)17-7-28(53)37(57)29(54)8-17)39(63-41(20)35)15-1-3-21(46)24(49)5-15/h1-12,14,33,36,39-40,42,45-58H,13H2/t33-,36-,39-,40-,42-/m1/s1
InChIKey: KTLUHRSHFRODPS-RIQPQZJCSA-N
DeepSMILES: OcccO)ccc6)O[C@@H][C@@H][C@H]6ccO)cccc6O[C@@H][C@@H]C6)OC=O)cccO)ccc6)O))O))))))))cccccc6)O))O)))))))))O))))))OC=O)cccO)ccc6)O))O))))))))cccccc6)O))O
Scaffold Graph/Node/Bond level: O=C(OC1Cc2cccc(C3c4ccccc4OC(c4ccccc4)C3OC(=O)c3ccccc3)c2OC1c1ccccc1)c1ccccc1
Scaffold Graph/Node level: OC(OC1CC2CCCC(C3C4CCCCC4OC(C4CCCCC4)C3OC(O)C3CCCCC3)C2OC1C1CCCCC1)C1CCCCC1
Scaffold Graph level: CC(CC1CC2CCCC(C3C4CCCCC4CC(C4CCCCC4)C3CC(C)C3CCCCC3)C2CC1C1CCCCC1)C1CCCCC1
Functional groups: cO; cOC; cC(=O)OC
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:
procyanidin b2 3,3'-di-o-gallate, Procyanidin B2 3,3'-di-O-gallate, procyanidin b-2 3,3'-di-o-gallate
External chemical identifiers:
CID:CID_124016; ChEMBL:CHEMBL39504; ChEBI:CHEBI:172846
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
3,3'-Digalloylprocyanidin B2
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 882.74
Log P RDKit 4.96
Topological polar surface area (Å2) RDKit 354.28
Number of hydrogen bond acceptors RDKit 20
Number of hydrogen bond donors RDKit 14
Number of carbon atoms RDKit 44
Number of heavy atoms RDKit 64
Number of heteroatoms RDKit 20
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 38
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.14
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 6
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 6
Total number of rings RDKit 8
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 8
3,3'-Digalloylprocyanidin B2
Drug-likeness
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 Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.0743813
3,3'-Digalloylprocyanidin B2
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly 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 -8.35
Number of PAINS structural alerts SwissADME 1
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
3,3'-Digalloylprocyanidin B2
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_001214ENSG00000126583PRKCG5582ChEMBL
TAR_EXP_001207ENSG00000154229PRKCA5578BindingDB, ChEMBL
TAR_EXP_001209ENSG00000166501PRKCB5579ChEMBL
TAR_EXP_001227ENSG00000067606PRKCZ5590ChEMBL
TAR_EXP_001212ENSG00000163932PRKCD5580ChEMBL
TAR_EXP_001213ENSG00000171132PRKCE5581ChEMBL
TAR_EXP_001215ENSG00000027075PRKCH5583ChEMBL
TAR_EXP_000496ENSG00000115825PRKD323683ChEMBL
TAR_EXP_001226ENSG00000065675PRKCQ5588ChEMBL, NPASS
TAR_EXP_001216ENSG00000163558PRKCI5584ChEMBL
TAR_EXP_001223ENSG00000184304PRKD15587ChEMBL