Structure Database (LMSD)

Common Name
(+)-Gallocatechin
Systematic Name
Synonyms
LM ID
LMPK12020002
Formula
Exact Mass
Calculate m/z
306.073955
Status
Curated


Classification

Biological Context

(+)-Gallocatechin is a polyphenol and flavonoid that has been isolated from the leaves of tea plants and has diverse biological activities.1,2,3 It inhibits the adherence of P. gingivalis onto human buccal epithelial cells by more than 50% when used at a concentration of 250 μg/ml.4 (+)-Gallocatechin has antimutagenic properties in UV-irradiated E. coli cells.2 It inhibits cell death induced by D-galactosamine and TNF-α in primary cultured mouse hepatocytes by 29.9% when used at a concentration of 80 μM.3 (+)-Gallocatechin (100 μM) inhibits HCT116 colorectal cancer cell proliferation by 57%.1

This information has been provided by Cayman Chemical

References

1. Du, G.J., Zhang, Z., Wen, X.D., et al. Epigallocatechin gallate (EGCG) is the most effective cancer chemopreventive polyphenol in green tea. Nutrients 4(11), 1679-1691 (2012).
2. Xiong, Q., Fan, W., Tezuka, Y., et al. Hepatoprotective effect of Apocynum venetum and its active constituents. Planta Med. 66(2), 127-133 (2000).
3. Matsuo, T., Hanamure, N., Shimoi, K., et al. Identification of (+)-gallocatechin as a bio-antimutagenic compound in Psidium guava leaves. Phytochemistry 36(4), 1027-1029 (1994).

String Representations

InChiKey (Click to copy)
XMOCLSLCDHWDHP-SWLSCSKDSA-N
InChi (Click to copy)
InChI=1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15+/m0/s1
SMILES (Click to copy)
C1(O)C=C2O[C@H](C3=CC(O)=C(O)C(O)=C3)[C@@H](O)CC2=C(O)C=1

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 3
Aromatic Rings 2
Rotatable Bonds 1
Van der Waals Molecular Volume 254.87
Topological Polar Surface Area 132.68
Hydrogen Bond Donors 6
Hydrogen Bond Acceptors 7
logP 1.54
Molar Refractivity 74.80

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Updated at
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