Structure Database (LMSD)
Common Name
Procyanidin B2
Systematic Name
Synonyms
3D model of Procyanidin B2
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Procyanidin B2 is a phenol and a dimer of (–)-epicatechin (Item No. 11807) that has been found in apple pomace and has diverse biological activities.1,2,3,4 It inhibits MCF-7 breast cancer cell proliferation (IC50 = 19.2 µM).1 Procyanidin B2 scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) and superoxide anion radicals in cell-free assays.2 It inhibits LDL oxidation in vitro by 79.5 and 98% when used at concentrations of 5 and 10 µM, respectively.3 Procyanidin B2 (100 mg/kg) prevents carbon tetrachloride-induced increases in serum aspartate aminotransferase (AST) and alanine aminotransferase (ALT) activities and hepatic injury in mice.4
This information has been provided by Cayman Chemical
References
1. Avelar, M.M., and Gouvêa, C.M.C.P. Procyanidin B2 cytotoxicity to MCF-7 human breast adenocarcinoma cells. Indian J. Pharm. Sci. 74(4), 351-355 (2012).
2. Lu, Y., and Foo, L.Y. Antioxidant and radical scavenging activities of polyphenols from apple pomace. Food Chem. 68(1), 81-85 (2000).
3. Teissedre, P.L., Frankel, E.N., Waterhouse, A.L., et al. Inhibition of in vitro human LDL oxidation by phenolic antioxidants from grapes and wines. J. Sci. Food Agric. 70(1), 55-61 (1996).
4. Yang, B.-Y., Zhang, X.-Y., Guan, S.-W., et al. Protective effect of procyanidin B2 against CCl4-induced acute liver injury in mice. Molecules 20(7), 12250-12265 (2015).
String Representations
InChiKey (Click to copy)
XFZJEEAOWLFHDH-NFJBMHMQSA-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-/m1/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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Updated at
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