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COCONUT Compound

(-)-Epicatechin gallate

CNP0278204.1 · C22H18O10 · View on COCONUT ↗

2D Structure

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Identifiers

Name(-)-Epicatechin gallate
IUPAC Name[(2~{R},3~{R})-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-chroman-3-yl] 3,4,5-trihydroxybenzoate
COCONUT IDCNP0278204.1
CAS1257-08-5
InChIKeyLSHVYAFMTMFKBA-TZIWHRDSSA-N
InChIInChI=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
SMILESO=C(O[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC=C(O)C(O)=C1)C1=CC(O)=C(O)C(O)=C1

Properties

Molecular FormulaC22H18O10
Molecular Weight442.38
Exact Mass442.09000
Log P (ALogP)2.53
TPSA177.14
H-Bond Donors / Acceptors7 / 10
Rotatable Bonds3
Lipinski's Rule of 5 Violations1
QED Drug-likeness0.24
NP-likeness1.84

Classification

NP PathwayShikimates and Phenylpropanoids
NP SuperclassFlavonoids
NP ClassFlavan-3-ols
Chemical SuperclassPhenylpropanoids and polyketides
Chemical ClassFlavonoids
Chemical SubclassFlavans

Reported in GR-MAPs Plants

Matricaria chamomilla as “Chamomilla recutita; Matricaria chamomilla; Matricaria recutita” in COCONUT
Mentha piperita as “Mentha piperita piperita; Mentha X piperita” in COCONUT
Daucus carota as “Daucus Carota” in COCONUT
Emblica officinalis as “Phyllanthus Emblica” in COCONUT
Oryza sativa as “Oryza sativa” in COCONUT

References (138)

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  2. 10.1002/(SICI)1521-4168(19990401)22:4<225::AID-JHRC225>3.0.CO;2-V
  3. 10.1002/JCCS.199900085
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  18. 10.1007/BF01201768
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  23. 10.1007/S10600-011-0016-0
  24. 10.1007/S11418-006-0119-2
  25. 10.1007/S11418-008-0239-Y
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  27. 10.1016/0031-9422(77)83041-0
  28. 10.1016/0031-9422(88)80455-2
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  31. 10.1016/0031-9422(92)80352-F
  32. 10.1016/0031-9422(92)80375-O
  33. 10.1016/0031-9422(93)85229-K
  34. 10.1016/0031-9422(93)85231-F
  35. 10.1016/0031-9422(93)85416-O
  36. 10.1016/0031-9422(96)00301-9
  37. 10.1016/0166-3542(93)90095-Z
  38. 10.1016/0308-8146(93)90160-H
  39. 10.1016/0378-8741(86)90110-8
  40. 10.1016/J.FCT.2007.08.007

Showing 40 of 138. See all references on COCONUT.

Data from COCONUT (COlleCtion of Open Natural prodUcTs), released under CC0. Chandrasekhar V. et al. COCONUT 2.0: a comprehensive overhaul and curation of the collection of open natural products database. Nucleic Acids Research (2024), doi:10.1093/nar/gkae1063. COCONUT release 2026-10.