Structure Database (LMSD)

Common Name
ent-Catechin 3-O-gallate
Systematic Name
Synonyms
LM ID
LMPK12020091
Formula
C22H18O10
Exact Mass
Calculate m/z
442.09
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
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Classification

Category
Main Class
Sub Class
Polyketides [PK]
Flavonoids [PK12]
Flavans, Flavanols and Leucoanthocyanidins [PK1202]

Biological Context

(–)-Catechin gallate ((–)-CG) is a catechin polyphenol that has been found in green tea extracts with diverse biological activities.1,2,3,4 It inhibits proliferation of MDA-MB-231 breast cancer cells and reduces VEGF-induced tyrosine phosphorylation of VEGF receptor 2 (VEGFR2) in bovine aortic endothelial cells (BAECs) in a concentration-dependent manner.1,2 (–)-CG is a competitive inhibitor of the facilitative glucose transporter GLUT4 (Ki = 90 μM) and inhibits methylglucose uptake by isolated rat adipocytes (IC50 = 50 μM).3 It is also lytic against T. cruzi amastigotes, with a 50% bactericidal concentration (MBC50) value of 48 pM.4

This information has been provided by Cayman Chemical

References

1. Sartippour, M.R., Heber, D., Ma, J., et al. Green tea and its catechins inhibit breast cancer xenografts. Nutr. Cancer 40(2), 149-156 (2001).
2. Paveto, C., Güida, M.C., Esteva, M.I., et al. Anti-Trypanosoma cruzi activity of green tea (Camellia sinensis) catechins. Antimicrob. Agents Chemother. 48(1), 69-74 (2004).
3. Lamy, S., Gingras, D., and Béliveau, R. Green tea catechins inhibit vascular endothelial growth factor receptor phosphorylation. Cancer Res. 62(2), 381-385 (2002).
4. Strobel, P., Allard, C., Perez-Acle, T., et al. Myricetin, quercetin and catechin-gallate inhibit glucose uptake in isolated rat adipocytes. Biochem. J. 386(Pt 3), 471-478 (2005).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Viridiplantae (#33090)
Flavonoid imported from http://metabolomics.jp/

String Representations

InChiKey (Click to copy)
LSHVYAFMTMFKBA-CTNGQTDRSA-N
InChi (Click to copy)
InChI=1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21+/m1/s1
SMILES (Click to copy)
C1(O)C=C2O[C@@H](C3C=C(O)C(O)=CC=3)[C@H](OC(C3C=C(O)C(O)=C(O)C=3)=O)CC2=C(O)C=1

Other Databases

HMDB ID
HMDB0029255
CHEBI ID
76131
METABOLOMICS ID
FL63ACNS0007
PubChem CID
6419835
Cayman ID
24963

Calculated Physicochemical Properties

Heavy Atoms 32
Rings 4
Aromatic Rings 3
Rotatable Bonds 4
Van der Waals Molecular Volume 368.52
Topological Polar Surface Area 179.21
Hydrogen Bond Donors 7
Hydrogen Bond Acceptors 10
logP 2.81
Molar Refractivity 107.77

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Updated at
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