Structure Database (LMSD)
Common Name
Procyanidin B3
Systematic Name
Synonyms
- Afzelechin-(4alpha->8)-afzelechin
3D model of Procyanidin B3
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Procyanidin B3 is a polyphenol flavonoid dimer of (+)-catechin that has been found in G. biloba and has diverse biological activities.1,2,3 It inhibits aggregation of amyloid-β (1-42) (Aβ42) with an IC50 value of 3.54 μM and destabilizes preformed Aβ42 fibrils (EC50 = 5.12 μM).1 Procyanidin B3 (1 mM) reduces oxidation of linoleic acid and scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radicals in cell-free assays.2 It inhibits hydrogen peroxide-induced production of inducible nitric oxide synthase (iNOS) and apoptosis in primary murine chondrocytes.3 Procyanidin B3 (0.01 mg/kg) reduces chondrocyte apoptosis, pseudocapsule thickness, and the frequency of ectopic cartilage formation in a mouse model of surgically induced osteoarthritis.
This information has been provided by Cayman Chemical
References
2. Ariga, T., Koshiyama, I., and Fukushima, D. Antioxidative properties of procyanidins B-1 and B-3 from azuki beans in aqueous systems. Agr. Biol. Chem. 52(11), 2717-2722 (2014).
3. Aini, H., Ochi, H., Iwata, M., et al. Procyanidin B3 prevents articular cartilage degeneration and heterotopic cartilage formation in a mouse surgical osteoarthritis model. PLoS One 7(5), e37728 (2012).
String Representations
InChiKey (Click to copy)
XFZJEEAOWLFHDH-AVFWISQGSA-N
InChi (Click to copy)
InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26-,27-,28+,29+/m0/s1
SMILES (Click to copy)
C1(O)=CC2O[C@H](C3C=CC(O)=C(O)C=3)[C@@H](O)[C@H](C3=C(O)C=C(O)C4C[C@H](O)[C@@H](C5C=CC(O)=C(O)C=5)OC=43)C=2C(O)=C1
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
Calculated Physicochemical Properties
Heavy Atoms
42
Rings
6
Aromatic Rings
4
Rotatable Bonds
3
Van der Waals Molecular Volume
483.60
Topological Polar Surface Area
224.90
Hydrogen Bond Donors
10
Hydrogen Bond Acceptors
12
logP
3.57
Molar Refractivity
144.41
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