Structure Database (LMSD)
Common Name
Epicatechin
Systematic Name
Synonyms
3D model of Epicatechin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
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
Admin
Created at
-
Updated at
8th Apr 2025