Structure Database (LMSD)

Common Name
Epicatechin
Systematic Name
Synonyms
LM ID
LMPK12020003
Formula
Exact Mass
Calculate m/z
290.07904
Status
Curated



Classification

Biological Context

(−)-Epicatechin is a polyketide synthase-derived polyphenol flavonoid that has been found in T. cacao and has diverse biological activities.1,2,3,4,5 It scavenges DPPH radicals in a cell-free assay when used at a concentration of 5 µM.2 (−)-Epicatechin inhibits COX-1 (IC50 = 3.2 μM).6 It acts synergistically with epigallocatechin gallate to induce apoptosis in, and reduce the proliferation of, PC-9 lung cancer cells when used at a concentration of 200 µM.4 (−)-Epicatechin (80 mg/kg) reduces LPS-induced increases in plasma creatinine and urea levels in a rat model of renal inflammation.5

This information has been provided by Cayman Chemical

References

5. Tauchen, J., Huml, L., Rimpelova, S., et al. Flavonoids and related members of the aromatic polyketide group in human health and disease: Do they really work? Molecules 25(17), 3846 (2020).

String Representations

InChiKey (Click to copy)
PFTAWBLQPZVEMU-UKRRQHHQSA-N
InChi (Click to copy)
InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
SMILES (Click to copy)
C1(O)C=C2O[C@H](C3=CC=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
PDB ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 3
Aromatic Rings 2
Rotatable Bonds 1
Van der Waals Molecular Volume 246.08
Topological Polar Surface Area 112.45
Hydrogen Bond Donors 5
Hydrogen Bond Acceptors 6
logP 1.83
Molar Refractivity 73.14

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Created at
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Updated at
8th Apr 2025