NP-MRD: Showing NP-Card for Epicatechin (NP0000562)

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Record Information

Version

2.0

Created at

2006-02-23 11:52:29 UTC

Updated at

2024-09-03 04:16:43 UTC

NP-MRD ID

NP0000562

Natural Product DOI

https://doi.org/10.57994/0773

Secondary Accession Numbers

NP0038094

Natural Product Identification

Common Name

Epicatechin

Description

Epicatechin is an antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms. Catechin is a tannin peculiar to green and white tea because the black tea oxidation process reduces catechins in black tea. Catechin is a powerful, water soluble polyphenol and antioxidant that is easily oxidized. Several thousand types are available in the plant world. As many as two thousand are known to have a flavon structure and are called flavonoids. Catechin is one of them. Green tea is manufactured from fresh, unfermented tea leaves; the oxidation of catechins is minimal, and hence they are able to serve as antioxidants. Researchers believe that catechin is effective because it easily sticks to proteins, blocking bacteria from adhering to cell walls and disrupting their ability to destroy them. Viruses have hooks on their surfaces and can attach to cell walls. The catechin in green tea prevents viruses from adhering and causing harm. Catechin reacts with toxins created by harmful bacteria (many of which belong to the protein family) and harmful metals such as lead, mercury, chrome, and cadmium. From its NMR espectra, there is a doubt on 2 and 3 atoms configuration. It seems to be that they are in trans position.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652306202122523D          

 35 37  0  0  0  0            999 V2000
   -1.2590   -5.4628    1.8399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1948   -4.1140    2.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8385   -3.5903    3.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7832   -2.2180    3.3818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4083   -1.6808    4.4721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0922   -1.3620    2.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4832   -1.9114    1.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5141   -3.2869    1.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2070   -1.1638    0.4624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1420    0.2361    0.4598 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6738    0.8950   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6057    1.9230   -0.4148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3166    2.5019   -1.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1000    2.0545   -2.7640 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7945    2.6214   -3.7934 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1878    1.0370   -3.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0233    0.6370   -4.3144 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4752    0.4568   -1.9723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0039    0.8137    1.8834 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3151    0.6178    2.4199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0170    0.1176    2.7950 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7425   -5.6907    1.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3682   -4.2600    3.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8052   -2.4006    4.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0127   -3.6888    0.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1941    0.3309    0.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8059    2.2910    0.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0358    3.2933   -1.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4817    2.1463   -4.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3800   -0.0921   -4.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2361   -0.3412   -2.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1952    1.8924    1.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5705   -0.3012    2.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7396    0.2820    3.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0129    0.5438    2.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  8  2  2  0  0  0  0
  4  3  2  0  0  0  0
 16 14  2  0  0  0  0
 11 18  2  0  0  0  0
  7  6  2  0  0  0  0
 14 13  1  0  0  0  0
 10 11  1  0  0  0  0
 13 12  2  0  0  0  0
 12 11  1  0  0  0  0
 14 15  1  0  0  0  0
  7  9  1  0  0  0  0
  6 21  1  0  0  0  0
 21 19  1  0  0  0  0
 19 10  1  0  0  0  0
 10  9  1  0  0  0  0
 18 16  1  0  0  0  0
  4  5  1  0  0  0  0
  2  3  1  0  0  0  0
  2  1  1  0  0  0  0
  4  6  1  0  0  0  0
 16 17  1  0  0  0  0
 19 20  1  0  0  0  0
 15 29  1  0  0  0  0
 10 26  1  6  0  0  0
 18 31  1  0  0  0  0
 13 28  1  0  0  0  0
 12 27  1  0  0  0  0
  8 25  1  0  0  0  0
  3 23  1  0  0  0  0
 21 34  1  0  0  0  0
 21 35  1  0  0  0  0
 19 32  1  6  0  0  0
  5 24  1  0  0  0  0
  1 22  1  0  0  0  0
 17 30  1  0  0  0  0
 20 33  1  0  0  0  0
M  END

HMDB0001871
     RDKit          3D
Epicatechin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.5765    2.6159    1.6847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8124    1.5456    1.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4013    0.4829    0.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6487   -0.5814    0.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2590   -1.6478   -0.5844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781   -0.6236    0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6895    0.4408    0.8785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4428    1.5053    1.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3049    0.4058    1.0381 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5062   -0.6400    0.5589 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8840   -0.1585    0.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0867    1.0107   -0.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3768    1.4135   -0.7039 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4775    0.6948   -0.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7786    1.0979   -0.5692 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2580   -0.4739    0.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3579   -1.2225    0.7988 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9609   -0.9104    0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1097   -1.2706   -0.6631 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2851   -0.3117   -1.6752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4908   -1.7696   -0.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1221    3.3662    2.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4736    0.4808    0.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2727   -1.6269   -0.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9429    2.3207    1.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5514   -1.4255    1.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376    1.5916   -0.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5641    2.3352   -1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9884    1.9464   -1.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417   -2.0827    1.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8226   -1.8324    1.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4946   -2.1229   -1.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0789    0.2387   -1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4634   -2.6200    0.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9345   -2.1722   -1.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 10 19  1  0
 19 20  1  0
 19 21  1  0
  8  2  1  0
 18 11  1  0
 21  6  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  0
  8 25  1  0
 10 26  1  1
 12 27  1  0
 13 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  6
 20 33  1  0
 21 34  1  0
 21 35  1  0
M  END


  Mrv1652306202122523D          

 35 37  0  0  0  0            999 V2000
   -1.2590   -5.4628    1.8399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1948   -4.1140    2.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8385   -3.5903    3.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7832   -2.2180    3.3818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4083   -1.6808    4.4721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0922   -1.3620    2.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4832   -1.9114    1.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5141   -3.2869    1.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2070   -1.1638    0.4624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1420    0.2361    0.4598 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6738    0.8950   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6057    1.9230   -0.4148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3166    2.5019   -1.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1000    2.0545   -2.7640 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7945    2.6214   -3.7934 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1878    1.0370   -3.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0233    0.6370   -4.3144 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4752    0.4568   -1.9723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0039    0.8137    1.8834 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3151    0.6178    2.4199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0170    0.1176    2.7950 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7425   -5.6907    1.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3682   -4.2600    3.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8052   -2.4006    4.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0127   -3.6888    0.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1941    0.3309    0.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8059    2.2910    0.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0358    3.2933   -1.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4817    2.1463   -4.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3800   -0.0921   -4.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2361   -0.3412   -2.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1952    1.8924    1.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5705   -0.3012    2.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7396    0.2820    3.8430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0129    0.5438    2.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  8  2  2  0  0  0  0
  4  3  2  0  0  0  0
 16 14  2  0  0  0  0
 11 18  2  0  0  0  0
  7  6  2  0  0  0  0
 14 13  1  0  0  0  0
 10 11  1  0  0  0  0
 13 12  2  0  0  0  0
 12 11  1  0  0  0  0
 14 15  1  0  0  0  0
  7  9  1  0  0  0  0
  6 21  1  0  0  0  0
 21 19  1  0  0  0  0
 19 10  1  0  0  0  0
 10  9  1  0  0  0  0
 18 16  1  0  0  0  0
  4  5  1  0  0  0  0
  2  3  1  0  0  0  0
  2  1  1  0  0  0  0
  4  6  1  0  0  0  0
 16 17  1  0  0  0  0
 19 20  1  0  0  0  0
 15 29  1  0  0  0  0
 10 26  1  6  0  0  0
 18 31  1  0  0  0  0
 13 28  1  0  0  0  0
 12 27  1  0  0  0  0
  8 25  1  0  0  0  0
  3 23  1  0  0  0  0
 21 34  1  0  0  0  0
 21 35  1  0  0  0  0
 19 32  1  6  0  0  0
  5 24  1  0  0  0  0
  1 22  1  0  0  0  0
 17 30  1  0  0  0  0
 20 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000562

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C(O[H])=C1[H])C([H])([H])[C@@]([H])(O[H])[C@]([H])(O2)C1=C([H])C(O[H])=C(O[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
PFTAWBLQPZVEMU-UKRRQHHQSA-N

> <FORMULA>
C15H14O6

> <MOLECULAR_WEIGHT>
290.2681

> <EXACT_MASS>
290.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
28.133242403815718

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <ALOGPS_LOGP>
1.02

> <JCHEM_LOGP>
1.795107015333333

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.624022697297178

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.004573813837975

> <JCHEM_PKA_STRONGEST_BASIC>
-3.289719332242856

> <JCHEM_POLAR_SURFACE_AREA>
110.38000000000001

> <JCHEM_REFRACTIVITY>
73.99970000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ent-epicatechin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001871
     RDKit          3D
Epicatechin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.5765    2.6159    1.6847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8124    1.5456    1.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4013    0.4829    0.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6487   -0.5814    0.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2590   -1.6478   -0.5844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781   -0.6236    0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6895    0.4408    0.8785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4428    1.5053    1.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3049    0.4058    1.0381 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5062   -0.6400    0.5589 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8840   -0.1585    0.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0867    1.0107   -0.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3768    1.4135   -0.7039 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4775    0.6948   -0.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7786    1.0979   -0.5692 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2580   -0.4739    0.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3579   -1.2225    0.7988 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9609   -0.9104    0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1097   -1.2706   -0.6631 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2851   -0.3117   -1.6752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4908   -1.7696   -0.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1221    3.3662    2.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4736    0.4808    0.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2727   -1.6269   -0.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9429    2.3207    1.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5514   -1.4255    1.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376    1.5916   -0.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5641    2.3352   -1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9884    1.9464   -1.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417   -2.0827    1.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8226   -1.8324    1.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4946   -2.1229   -1.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0789    0.2387   -1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4634   -2.6200    0.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9345   -2.1722   -1.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 10 19  1  0
 19 20  1  0
 19 21  1  0
  8  2  1  0
 18 11  1  0
 21  6  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  0
  8 25  1  0
 10 26  1  1
 12 27  1  0
 13 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  6
 20 33  1  0
 21 34  1  0
 21 35  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  O   UNK     0      -1.259  -5.463   1.840  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.195  -4.114   2.033  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.839  -3.590   3.147  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.783  -2.218   3.382  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.408  -1.681   4.472  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.092  -1.362   2.516  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.483  -1.911   1.381  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.514  -3.287   1.147  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.207  -1.164   0.462  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.142   0.236   0.460  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.674   0.895  -0.645  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.606   1.923  -0.415  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.317   2.502  -1.472  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.100   2.054  -2.764  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.795   2.621  -3.793  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.188   1.037  -3.017  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.023   0.637  -4.314  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.475   0.457  -1.972  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.004   0.814   1.883  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.315   0.618   2.420  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.017   0.118   2.795  0.00  0.00           C+0
HETATM   22  H   UNK     0      -0.743  -5.691   1.049  0.00  0.00           H+0
HETATM   23  H   UNK     0      -2.368  -4.260   3.817  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.805  -2.401   4.991  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.013  -3.689   0.272  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.194   0.331   0.149  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.806   2.291   0.589  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.036   3.293  -1.282  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.482   2.146  -4.589  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.380  -0.092  -4.325  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.236  -0.341  -2.168  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.195   1.892   1.896  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.571  -0.301   2.212  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.740   0.282   3.843  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.013   0.544   2.623  0.00  0.00           H+0
CONECT    1    2   22                                                       
CONECT    2    8    3    1                                                  
CONECT    3    4    2   23                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4   24                                                       
CONECT    6    7   21    4                                                  
CONECT    7    8    6    9                                                  
CONECT    8    7    2   25                                                  
CONECT    9    7   10                                                       
CONECT   10   11   19    9   26                                             
CONECT   11   18   10   12                                                  
CONECT   12   13   11   27                                                  
CONECT   13   14   12   28                                                  
CONECT   14   16   13   15                                                  
CONECT   15   14   29                                                       
CONECT   16   14   18   17                                                  
CONECT   17   16   30                                                       
CONECT   18   11   16   31                                                  
CONECT   19   21   10   20   32                                             
CONECT   20   19   33                                                       
CONECT   21    6   19   34   35                                             
CONECT   22    1                                                            
CONECT   23    3                                                            
CONECT   24    5                                                            
CONECT   25    8                                                            
CONECT   26   10                                                            
CONECT   27   12                                                            
CONECT   28   13                                                            
CONECT   29   15                                                            
CONECT   30   17                                                            
CONECT   31   18                                                            
CONECT   32   19                                                            
CONECT   33   20                                                            
CONECT   34   21                                                            
CONECT   35   21                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

COMPND    HMDB0001871
HETATM    1  O1  UNL     1      -4.576   2.616   1.685  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.812   1.546   1.203  1.00  0.00           C  
HETATM    3  C2  UNL     1      -4.401   0.483   0.552  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.649  -0.581   0.072  1.00  0.00           C  
HETATM    5  O2  UNL     1      -4.259  -1.648  -0.584  1.00  0.00           O  
HETATM    6  C4  UNL     1      -2.278  -0.624   0.226  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.689   0.441   0.879  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.443   1.505   1.358  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.305   0.406   1.038  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.506  -0.640   0.559  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.884  -0.158   0.248  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.087   1.011  -0.441  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.377   1.413  -0.704  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.478   0.695  -0.306  1.00  0.00           C  
HETATM   15  O4  UNL     1       5.779   1.098  -0.569  1.00  0.00           O  
HETATM   16  C12 UNL     1       4.258  -0.474   0.383  1.00  0.00           C  
HETATM   17  O5  UNL     1       5.358  -1.223   0.799  1.00  0.00           O  
HETATM   18  C13 UNL     1       2.961  -0.910   0.666  1.00  0.00           C  
HETATM   19  C14 UNL     1      -0.110  -1.271  -0.663  1.00  0.00           C  
HETATM   20  O6  UNL     1      -0.285  -0.312  -1.675  1.00  0.00           O  
HETATM   21  C15 UNL     1      -1.491  -1.770  -0.293  1.00  0.00           C  
HETATM   22  H1  UNL     1      -4.122   3.366   2.150  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.474   0.481   0.412  1.00  0.00           H  
HETATM   24  H3  UNL     1      -5.273  -1.627  -0.704  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.943   2.321   1.864  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.551  -1.425   1.349  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.238   1.592  -0.764  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.564   2.335  -1.248  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.988   1.946  -1.071  1.00  0.00           H  
HETATM   30  H9  UNL     1       5.242  -2.083   1.305  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.823  -1.832   1.209  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.495  -2.123  -1.008  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.079   0.239  -1.501  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.463  -2.620   0.413  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.934  -2.172  -1.242  1.00  0.00           H  
CONECT    1    2   22
CONECT    2    3    3    8
CONECT    3    4   23
CONECT    4    5    6    6
CONECT    5   24
CONECT    6    7   21
CONECT    7    8    8    9
CONECT    8   25
CONECT    9   10
CONECT   10   11   19   26
CONECT   11   12   12   18
CONECT   12   13   27
CONECT   13   14   14   28
CONECT   14   15   16
CONECT   15   29
CONECT   16   17   18   18
CONECT   17   30
CONECT   18   31
CONECT   19   20   21   32
CONECT   20   33
CONECT   21   34   35
END

HMDB0001871
     RDKit          3D
Epicatechin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.5765    2.6159    1.6847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8124    1.5456    1.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4013    0.4829    0.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6487   -0.5814    0.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2590   -1.6478   -0.5844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781   -0.6236    0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6895    0.4408    0.8785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4428    1.5053    1.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3049    0.4058    1.0381 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5062   -0.6400    0.5589 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8840   -0.1585    0.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0867    1.0107   -0.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3768    1.4135   -0.7039 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4775    0.6948   -0.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7786    1.0979   -0.5692 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2580   -0.4739    0.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3579   -1.2225    0.7988 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9609   -0.9104    0.6660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1097   -1.2706   -0.6631 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2851   -0.3117   -1.6752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4908   -1.7696   -0.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1221    3.3662    2.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4736    0.4808    0.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2727   -1.6269   -0.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9429    2.3207    1.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5514   -1.4255    1.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376    1.5916   -0.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5641    2.3352   -1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9884    1.9464   -1.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417   -2.0827    1.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8226   -1.8324    1.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4946   -2.1229   -1.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0789    0.2387   -1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4634   -2.6200    0.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9345   -2.1722   -1.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 10 19  1  0
 19 20  1  0
 19 21  1  0
  8  2  1  0
 18 11  1  0
 21  6  1  0
  1 22  1  0
  3 23  1  0
  5 24  1  0
  8 25  1  0
 10 26  1  1
 12 27  1  0
 13 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  6
 20 33  1  0
 21 34  1  0
 21 35  1  0
M  END

View in JSmol

Synonyms

Value	Source
(-)-Epicatechin	HMDB
(-)-Epicatechol	HMDB
(2R,3R)-(-)-Epicatechin	HMDB
3,3',4',5,7-Pentahydroxyflavane	HMDB
alpha-Catechin	HMDB
Epicatechol	HMDB
Epigallocatechin	HMDB
L(-)-Epicatechin	HMDB
L-Acacatechin	HMDB
L-Epicatechin	HMDB
L-Epicatechol	HMDB
3,3',4',5,7-Flavanpentol	HMDB
Cyanidanol 3	HMDB
Cyanidanol-3	HMDB
(+)-Catechin	HMDB
(+)-Cyanidanol	HMDB
Acid, catechuic	HMDB
Cianidanol	HMDB
Acid, catechinic	HMDB
Catechin	HMDB
Catechinic acid	HMDB
Catechuic acid	HMDB
Catergen	HMDB
KB-53	HMDB
Zyma	HMDB
(+)-Cyanidanol-3	HMDB
KB 53	HMDB
Epi-catechin	HMDB
Epicatechin	PhytoBank

Chemical Formula

C₁₅H₁₄O₆

Average Mass

290.2681 Da

Monoisotopic Mass

290.07904 Da

IUPAC Name

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Traditional Name

ent-epicatechin

CAS Registry Number

490-46-0

SMILES

[H]OC1=C([H])C2=C(C(O[H])=C1[H])C([H])([H])[C@@]([H])(O[H])[C@]([H])(O2)C1=C([H])C(O[H])=C(O[H])C([H])=C1[H]

InChI Identifier

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

InChI Key

PFTAWBLQPZVEMU-UKRRQHHQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, simulated)	Ahselim			2022-07-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, simulated)	Ahselim			2022-02-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	ztmnb@umsystem.edu	Not Available	Not Available	2023-07-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	ztmnb@umsystem.edu	Not Available	Not Available	2023-07-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.132100455, CD₃OD, simulated)	ztmnb@umsystem.edu	Sumner lab, University of Missouri	Zach Tretter	2024-05-14	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Abutilon theophrasti	LOTUS Database	35616633
Acacia adunca	KNApSAcK Database	22123792
Acacia baileyana	KNApSAcK Database	22123792
Acacia calamifolia	KNApSAcK Database	22123792
Acacia catechu	KNApSAcK Database	22123792
Acacia clunies-rossiae	KNApSAcK Database	22123792
Acacia concurrens	KNApSAcK Database	22123792
Acacia confusa	LOTUS Database	35616633
Acacia dealbata	KNApSAcK Database	22123792
Acacia deanei	KNApSAcK Database	22123792
Acacia falciformis	KNApSAcK Database	22123792
Acacia fimbriata	KNApSAcK Database	22123792
Acacia homalophylla	KNApSAcK Database	22123792
Acacia implexa	LOTUS Database	35616633
Acacia ixiophylla	KNApSAcK Database	22123792
Acacia karoo	LOTUS Database	35616633
Acacia lanigera	KNApSAcK Database	22123792
Acacia mabellae	KNApSAcK Database	22123792
Acacia mearnsii	LOTUS Database	35616633
Acacia melanoxylon	KNApSAcK Database	22123792
Acacia mollifolia	KNApSAcK Database	22123792
Acacia nilotica	KNApSAcK Database	22123792
Acacia obtusifolia	KNApSAcK Database	22123792
Acacia oswaldii	KNApSAcK Database	22123792
Acacia pendula	KNApSAcK Database	22123792
Acacia polyacantha	LOTUS Database	35616633
Acacia pycnantha	KNApSAcK Database	22123792
Acacia retinodes	KNApSAcK Database	22123792
Acacia rigens	KNApSAcK Database	22123792
Acacia verniciflua	KNApSAcK Database	22123792
Acer barbinerve	LOTUS Database	35616633
Acer nikoense	KNApSAcK Database	22123792
Actinidia arguta	LOTUS Database	35616633
Actinidia chinensis	LOTUS Database	35616633
Aesculus californica	KNApSAcK Database	22123792
Aesculus carnea	KNApSAcK Database	22123792
Aesculus hippocastanum	LOTUS Database	35616633
Albizia lebbeck	LOTUS Database	35616633
Alhagi sparsifolia	LOTUS Database	35616633
Allium sativum	KNApSAcK Database	22123792
Alnus hirsuta	LOTUS Database	35616633
Alpinia zerumbet	LOTUS Database	35616633
Ampelopsis glandulosa	LOTUS Database	35616633
Ampelopsis japonica	KNApSAcK Database	22123792
Ananas comosus	LOTUS Database	35616633
Anchomanes difformis	LOTUS Database	35616633
Annona muricata	KNApSAcK Database	22123792
Apocynum venetum	LOTUS Database	35616633
Arabidopsis thaliana	KNApSAcK Database	22123792
Arbutus andrachne L.	LOTUS Database	35616633
Arbutus unedo	LOTUS Database	35616633
Areca catechu	LOTUS Database	35616633
Averrhoa carambola	Plant	KNApSAcK
Averrhoa carambola L.	KNApSAcK Database	22123792
Azadirachta indica	KNApSAcK Database	22123792
Banisteriopsis caapi	LOTUS Database	35616633
Bauhinia racemosa	LOTUS Database	35616633
Begonia fagifolia	LOTUS Database	35616633
Berchemia racemosa	LOTUS Database	35616633
Berneuxia thibetica	LOTUS Database	35616633
Betula pubescens	LOTUS Database	35616633
Brosimopsis acutifolium	KNApSAcK Database	22123792
Burkea africana	LOTUS Database	35616633
Byrsonima crassifolia	LOTUS Database	35616633
Calluna vulgaris	LOTUS Database	35616633
Calophyllum enervosum	KNApSAcK Database	22123792
Calophyllum inophyllum	LOTUS Database	35616633
Calycolpus warszewiczianus	KNApSAcK Database	22123792
Camellia crassicolumna	LOTUS Database	35616633
Camellia irrawadiensis	LOTUS Database	35616633
Camellia japonica	KNApSAcK Database	22123792
Camellia sinensis	KNApSAcK Database	22123792
Camellia sinensis (L.) O.KUNTZE	KNApSAcK Database	22123792
Campylospermum flavum	LOTUS Database	35616633
Campylotropis hirtella	LOTUS Database	35616633
Cannabis sativa	CannabisDB	Not Available
Cassia angustifolia	Plant	KNApSAcK
Cassia fistula	KNApSAcK Database	22123792
Cassia grandis	Plant	KNApSAcK
Cassia javanica	KNApSAcK Database	22123792
Castanopsis hystrix	LOTUS Database	35616633
Cecropia glaziovii	LOTUS Database	35616633
Cecropia hololeuca	LOTUS Database	35616633
Celastrus angulatus	LOTUS Database	35616633
Celastrus flagellaris	LOTUS Database	35616633
Celastrus orbiculatus	KNApSAcK Database	22123792
Ceratiola ericoides	LOTUS Database	35616633
Chaenomeles japonica	KNApSAcK Database	22123792
Chaenomeles sinensis	LOTUS Database	35616633
Chamaecyparis formosensis	KNApSAcK Database	22123792
Chimarrhis turbinata	LOTUS Database	35616633
Chrysophyllum cainito	LOTUS Database	35616633
Cinchona succirubra	KNApSAcK Database	22123792
Cinnamomum aromaticum	LOTUS Database	35616633
Cinnamomum bejolghota	LOTUS Database	35616633
Cinnamomum cassia Blume.	KNApSAcK Database	22123792
Cinnamomum kotoense	LOTUS Database	35616633
Cinnamomum obtusifolium Nees.	KNApSAcK Database	22123792
Cinnamomum philippinense	LOTUS Database	35616633
Cinnamomum sieboldii	KNApSAcK Database	22123792
Cinnamomum subavenium	KNApSAcK Database	22123792
Cinnamomum tenuifolium	LOTUS Database	35616633
Cinnamomum triplinerve	LOTUS Database	35616633
Cinnamomum verum	LOTUS Database	35616633
Cistus incanus	LOTUS Database	35616633
Cistus salviifolius	KNApSAcK Database	22123792
Cola acuminata	LOTUS Database	35616633
Coleogyne ramosissima	LOTUS Database	35616633
Coleogyne ramosissima Torr.	KNApSAcK Database	22123792
Colophospermum mopane	KNApSAcK Database	22123792
Combretum quadrangulare	KNApSAcK Database	22123792
Convallaria keiskei	KNApSAcK Database	22123792
Cotoneaster orbicularis	LOTUS Database	35616633
Cowania mexicana	KNApSAcK Database	22123792
Crataegus laevigata	LOTUS Database	35616633
Crataegus monogyna	KNApSAcK Database	22123792
Crataegus rhipidophylla	LOTUS Database	35616633
Crataegus sinaica	LOTUS Database	35616633
Cratoxylum formosum	LOTUS Database	35616633
Croton insularis	LOTUS Database	35616633
Croton lechleri	LOTUS Database	35616633
Croton lechleri Mull.Arg.	KNApSAcK Database	22123792
Cryptocarya obovata	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Cupania latifolia	LOTUS Database	35616633
Cupressus sempervirens	LOTUS Database	35616633
Cycas circinalis	LOTUS Database	35616633
Cyperus longus	LOTUS Database	35616633
Dalbergia frutescens	LOTUS Database	35616633
Davallia divaricata	LOTUS Database	35616633
Davallia mariesii	LOTUS Database	35616633
Delavaya toxocarpa	LOTUS Database	35616633
Detarium microcarpum	LOTUS Database	35616633
Dicranopteris pedata	KNApSAcK Database	22123792
Dimocarpus longan	LOTUS Database	35616633
Dioscorea bulbifera	LOTUS Database	35616633
Dioscorea cirrhosa	LOTUS Database	35616633
Diospyros kaki	LOTUS Database	35616633
Dorstenia contrajerva	LOTUS Database	35616633
Drynaria fortunei Kunze J.SM.	KNApSAcK Database	22123792
Ecdysanthera utilis	KNApSAcK Database	22123792
Ekebergia capensis	LOTUS Database	35616633
Elaeagnus angustifolia	KNApSAcK Database	22123792
Elaeagnus glabra	LOTUS Database	35616633
Entada phaseoloides	LOTUS Database	35616633
Ephedra nebrodensis	KNApSAcK Database	22123792
Ephedra sinica	KNApSAcK Database	22123792
Erica arborea	LOTUS Database	35616633
Eriobotrya japonica	KNApSAcK Database	22123792
Erythroxylum cambodianum	KNApSAcK Database	22123792
Erythroxylum leal-costae	Plant	KNApSAcK
Erythroxylum passerinum	LOTUS Database	35616633
Erythroxylum rimosum	Plant	KNApSAcK
Euclea crispa	LOTUS Database	35616633
Euterpe oleracea	KNApSAcK Database	22123792
Eysenhardtia subcoriacea Pennell	KNApSAcK Database	22123792
Fagopyrum acutatum	LOTUS Database	35616633
Fagopyrum esculentum	KNApSAcK Database	22123792
Fagopyrum homotropicum	KNApSAcK Database	22123792
Ficus microcarpa	LOTUS Database	35616633
Fragaria vesca	LOTUS Database	35616633
Fugopyrum esculentum calli	-	KNApSAcK
Garcinia celebica	KNApSAcK Database	22123792
Garcinia cornea	KNApSAcK Database	22123792
Garcinia dulcis	KNApSAcK Database	22123792
Garcinia eugenifolia	KNApSAcK Database	22123792
Garcinia mangostana	KNApSAcK Database	22123792
Garcinia speciosa	KNApSAcK Database	22123792
Geranium pratense	KNApSAcK Database	22123792
Geranium thunbergii	LOTUS Database	35616633
Ginkgo biloba	KNApSAcK Database	22123792
Glycine max	LOTUS Database	35616633
Gossypium hirsutum	LOTUS Database	35616633
Guazuma ulmifolia	LOTUS Database	35616633
Gymnosporia pyria	LOTUS Database	35616633
Hedysarum theinum	LOTUS Database	35616633
Hibiscus cannabinus	LOTUS Database	35616633
Humulus lupulus	KNApSAcK Database	22123792
Hypericum erectum	LOTUS Database	35616633
Hypericum hirsutum	LOTUS Database	35616633
Hypericum maculatum	LOTUS Database	35616633
Hypericum monogynum	LOTUS Database	35616633
Hypericum patulum	LOTUS Database	35616633
Hypericum perforatum	KNApSAcK Database	22123792
Hypericum triquetrifolium	LOTUS Database	35616633
Ixora coccinea	LOTUS Database	35616633
Juniperus excelsa	LOTUS Database	35616633
Kadsura heteroclita	KNApSAcK Database	22123792
Kandelia candel	LOTUS Database	35616633
Koenigia coriaria	LOTUS Database	35616633
Koenigia divaricata	LOTUS Database	35616633
Kummerowia stipulacea	LOTUS Database	35616633
Larix decidua Miller.	KNApSAcK Database	22123792
Larix gmelini	LOTUS Database	35616633
Larix sibirica	KNApSAcK Database	22123792
Laurus nobilis	KNApSAcK Database	22123792
Laurus nobilis L.	Plant	KNApSAcK
Lens culinaris	LOTUS Database	35616633
Leptarrhena pyrolifolia	LOTUS Database	35616633
Ligaria cuneifolia	LOTUS Database	35616633
Lindera aggregata	LOTUS Database	35616633
Lindera umbellata	LOTUS Database	35616633
Litchi chinensis	LOTUS Database	35616633
Litsea glutinosa	LOTUS Database	35616633
Litsea rotundifolia	LOTUS Database	35616633
Litsea szemaois	LOTUS Database	35616633
Lophira lanceolata	LOTUS Database	35616633
Lotus corniculatus	LOTUS Database	35616633
Lotus pedunculatus	LOTUS Database	35616633
Lupinus albus	KNApSAcK Database	22123792
Lupinus angustifolius	LOTUS Database	35616633
Lyonia ovalifolia	LOTUS Database	35616633
Machilus thunbergii	LOTUS Database	35616633
Malus domestica	LOTUS Database	35616633
Malus pumila	LOTUS Database	35616633
Malus sylvestris	LOTUS Database	35616633
Mammea americana	LOTUS Database	35616633
Mandevilla martiana	LOTUS Database	35616633
Mangifera indica	LOTUS Database	35616633
Manilkara zapota	LOTUS Database	35616633
Manilkara zapota cv.Tikal	KNApSAcK Database	22123792
Margyricarpus pinnatus	LOTUS Database	35616633
Matricaria chamomilla	LOTUS Database	35616633
Maytenus boaria	LOTUS Database	35616633
Maytenus disticha	LOTUS Database	35616633
Maytenus heterophylla	KNApSAcK Database	22123792
Medicago sativa	LOTUS Database	35616633
Medicago truncatula	KNApSAcK Database	22123792
Mesua ferrea	LOTUS Database	35616633
Mezoneuron benthamianum	LOTUS Database	35616633
Microtropis fokienensis	LOTUS Database	35616633
Miliusa balansae	LOTUS Database	35616633
Millettia brandisiana	KNApSAcK Database	22123792
Mitragyna rotundifolia	Plant	KNApSAcK
Mitragyna speciosa	Plant	KNApSAcK
Momordica charantia	KNApSAcK Database	22123792
Monteverdia ilicifolia	LOTUS Database	35616633
Moringa oleifera	Plant	KNApSAcK
Moringa peregrina	Plant	KNApSAcK
Moringa stenopetala	Plant	KNApSAcK
Muehlenbeckia hastulata	LOTUS Database	35616633
Musa acuminata	KNApSAcK Database	22123792
Myrica nagi	KNApSAcK Database	22123792
Nageia nagi	Plant	KNApSAcK
Nelia pillansii	LOTUS Database	35616633
Neocheiropteris fortunei	LOTUS Database	35616633
Ochna afzelii	LOTUS Database	35616633
Ochna beddomei	KNApSAcK Database	22123792
Ocotea porosa	LOTUS Database	35616633
Oenothera biennis	LOTUS Database	35616633
Onobrychis cyri	LOTUS Database	35616633
Parameria laevigata	LOTUS Database	35616633
Paullinia cupana	LOTUS Database	35616633
Pavetta owariensis	LOTUS Database	35616633
Pentadesma butyracea	LOTUS Database	35616633
Persea americana	LOTUS Database	35616633
Persicaria hydropiper	LOTUS Database	35616633
Phaseolus vulgaris	LOTUS Database	35616633
Phoenix dactylifera	LOTUS Database	35616633
Phoenix hanceana var. formosana	KNApSAcK Database	22123792
Phoenix loureiroi	LOTUS Database	35616633
Phyllanthus emblica	KNApSAcK Database	22123792
Phyllanthus klotzschianus	LOTUS Database	35616633
Phyllanthus niruri	LOTUS Database	35616633
Phyllocladus alpinus	LOTUS Database	35616633
Phyllocladus trichomanoides	LOTUS Database	35616633
Picea abies	LOTUS Database	35616633
Pinus sibirica L.	KNApSAcK Database	22123792
Pinus sylvestris	Plant	KNApSAcK
Pinus sylvestris L.	KNApSAcK Database	22123792
Platanus orientalis	LOTUS Database	35616633
Podocarpus nagi	KNApSAcK Database	22123792
Polygonum bistorta	KNApSAcK Database	22123792
Polygonum cuspidatum	Plant	KNApSAcK
Polygonum hydropiper	KNApSAcK Database	22123792
Polygonum sachalinensis	Plant	KNApSAcK
Potentilla anserina	KNApSAcK Database	22123792
Potentilla fruticosa	LOTUS Database	35616633
Prinsepia utilis	LOTUS Database	35616633
Prosopis juliflora	LOTUS Database	35616633
Prunus armeniaca	LOTUS Database	35616633
Prunus avium	KNApSAcK Database	22123792
Prunus domestica	KNApSAcK Database	22123792
Prunus laurocerasus	LOTUS Database	35616633
Prunus maximowiczii	LOTUS Database	35616633
Prunus mume	LOTUS Database	35616633
Prunus persica	LOTUS Database	35616633
Prunus spinosa	LOTUS Database	35616633
Prunus ssiori	LOTUS Database	35616633
Pseudotsuga menziesii	LOTUS Database	35616633
Psorospermum febrifugum	LOTUS Database	35616633
Pterocarpus marsupium	KNApSAcK Database	22123792
Punica granatum	KNApSAcK Database	22123792
Punica granatum L.	KNApSAcK Database	22123792
Pyracantha coccinea	LOTUS Database	35616633
Pyrus communis	LOTUS Database	35616633
Quercus glauca	LOTUS Database	35616633
Quercus marilandica	LOTUS Database	35616633
Quercus miyagii	LOTUS Database	35616633
Quercus robur	LOTUS Database	35616633
Rhamnus lycioides	LOTUS Database	35616633
Rhaphiolepis bibas	Plant	KNApSAcK
Rheum australe	Plant	KNApSAcK
Rheum emodi	KNApSAcK Database	22123792
Rhizophora stylosa	LOTUS Database	35616633
Rhodiola crenulata	KNApSAcK Database	22123792
Rhodiola semenovii	LOTUS Database	35616633
Rhododendron brachycarpum ssp.brachycarpum	KNApSAcK Database	22123792
Rhododendron calophytum	KNApSAcK Database	22123792
Rhododendron catawbiense	KNApSAcK Database	22123792
Rhododendron Cunningham's white	KNApSAcK Database	22123792
Rhododendron dauricum	LOTUS Database	35616633
Rhododendron decorum	LOTUS Database	35616633
Rhododendron degronianum ssp. Heptamerum var. hondoense	KNApSAcK Database	22123792
Rhododendron dichroanthum ssp.scyphocalyx	KNApSAcK Database	22123792
Rhododendron fortunei	KNApSAcK Database	22123792
Rhododendron galactinum	KNApSAcK Database	22123792
Rhododendron insigne	KNApSAcK Database	22123792
Rhododendron kaempferi	KNApSAcK Database	22123792
Rhododendron micranthum	KNApSAcK Database	22123792
Rhododendron mucronatum	KNApSAcK Database	22123792
Rhododendron oreotrephes	KNApSAcK Database	22123792
Rhododendron ponticum	KNApSAcK Database	22123792
Rhododendron praevernum	KNApSAcK Database	22123792
Rhododendron smirnowii	KNApSAcK Database	22123792
Rhododendron spinuliferum	LOTUS Database	35616633
Rhododendron ungernii	KNApSAcK Database	22123792
Rhus glabra	LOTUS Database	35616633
Ribes nigrum	LOTUS Database	35616633
Rosa chinensis	LOTUS Database	35616633
Rosa henryi	LOTUS Database	35616633
Rosa rugosa	LOTUS Database	35616633
Rubus glaucus	LOTUS Database	35616633
Rumex acetosa	LOTUS Database	35616633
Rumex dentatus	Plant	KNApSAcK
Rumex japonicus	KNApSAcK Database	22123792
Rumex thyrsiflorus	Plant	KNApSAcK
Rumex vesicarius	Plant	KNApSAcK
Salacia chinensis	LOTUS Database	35616633
Salacia prinoides	KNApSAcK Database	22123792
Salacia reticulata	LOTUS Database	35616633
Saraca asoca	KNApSAcK Database	22123792
Schisandra lancifolia	LOTUS Database	35616633
Schotia brachypetala	KNApSAcK Database	22123792
Schotia latifolia	LOTUS Database	35616633
Scurrula atropurpurea	KNApSAcK Database	22123792
Scurrura atropurpurea	-	KNApSAcK
Semialarium mexicanum	LOTUS Database	35616633
Sequoia sempervirens	LOTUS Database	35616633
Smilax china	LOTUS Database	35616633
Smilax corbularia	LOTUS Database	35616633
Solanum tuberosum subsp. Andigena	KNApSAcK Database	22123792
Sophora flavescens	KNApSAcK Database	22123792
Sophora japonica	KNApSAcK Database	22123792
Sorbus decora	LOTUS Database	35616633
Sorghum bicolor	LOTUS Database	35616633
Spathelia excelsa	LOTUS Database	35616633
Spatholobus suberectus	KNApSAcK Database	22123792
Spiraea hypericifolia	LOTUS Database	35616633
Stachyurus himalaicus	LOTUS Database	35616633
Strobilanthes crispus	Plant	KNApSAcK
Styphnolobium japonicum	Plant	KNApSAcK
Tamarindus indica	KNApSAcK Database	22123792
Taxus cuspidata	LOTUS Database	35616633
Taxus mairei	LOTUS Database	35616633
Taxus media	Plant	KNApSAcK
Tectaria subtriphylla	LOTUS Database	35616633
Terminalia arjuna	Plant	KNApSAcK
Terminalia catappa	Plant	KNApSAcK
Terminalia glabrescens	LOTUS Database	35616633
Terminalia mollis	Plant	KNApSAcK
Theobroma cacao	KNApSAcK Database	22123792
Theobroma grandiflorum	KNApSAcK Database	22123792
Thujopsis dolabrata	LOTUS Database	35616633
Toona sinensis	KNApSAcK Database	22123792
Trichilia catigua	LOTUS Database	35616633
Trifolium pratense	Plant	KNApSAcK
Tripterospermum chinense	LOTUS Database	35616633
Tsuga chinensis	LOTUS Database	35616633
Typha capensis	LOTUS Database	35616633
Typha capensis (Rohrb.) N. E. Br	KNApSAcK Database	22123792
Uncaria elliptica	KNApSAcK Database	22123792
Uncaria gambir	KNApSAcK Database	22123792
Uncaria guianensis	LOTUS Database	35616633
Uncaria rhynchophylla	KNApSAcK Database	22123792
Uncaria sinensis	LOTUS Database	35616633
Uncaria tomentosa	KNApSAcK Database	22123792
Urceola micrantha	LOTUS Database	35616633
Vaccinium angustifolium	LOTUS Database	35616633
Vaccinium macrocarpon	KNApSAcK Database	22123792
Vaccinium reticulatum	LOTUS Database	35616633
Vaccinium vitis-idaea	KNApSAcK Database	22123792
Vachellia nilotica	LOTUS Database	35616633
Viburnum opulus	LOTUS Database	35616633
Vicia faba	KNApSAcK Database	22123792
Visnea mocanera	LOTUS Database	35616633
Vitellaria paradoxa	LOTUS Database	35616633
Vitis vinifera	KNApSAcK Database	22123792
Vitis vinifera L.	Plant	KNApSAcK
Walsura yunnanensis	LOTUS Database	35616633
Waltheria indica	LOTUS Database	35616633
Wisteria floribunda	LOTUS Database	35616633
Wisteria sinensis	KNApSAcK Database	22123792
Woodwardia orientalis	LOTUS Database	35616633
Xanthoceras sorbifolia	KNApSAcK Database	22123792
Xanthoceras sorbifolium	Plant	KNApSAcK
Xylopia vielana	KNApSAcK Database	22123792
Zanthoxylum piperitum	LOTUS Database	35616633
Ziziphus jujuba	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Catechins

Alternative Parents

Substituents

Catechin
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Chromane
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Ether
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

polyphenol (CHEBI:90 )
catechin (CHEBI:90 )
Flavans, Flavanols and Leucoanthocyanidins (C09727 )
Flavan 3-ols (C09727 )
Condensed tannins (Proanthocyanidins) (C09727 )
Flavans, Flavanols and Leucoanthocyanidins (LMPK12020003 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	240 °C	Not Available
Boiling Point	630.40 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	63110 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.490 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
Water Solubility	0.64 g/L	ALOGPS
logP	1.02	ALOGPS
logP	1.8	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	9	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74 m³·mol⁻¹	ChemAxon
Polarizability	28.13 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0001871

DrugBank ID

DB12039

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Catechin

METLIN ID

3420

PubChem Compound

72276

PDB ID

Not Available

ChEBI ID

Good Scents ID

rw1136801

References

General References

Li C, Meng X, Winnik B, Lee MJ, Lu H, Sheng S, Buckley B, Yang CS: Analysis of urinary metabolites of tea catechins by liquid chromatography/electrospray ionization mass spectrometry. Chem Res Toxicol. 2001 Jun;14(6):702-7. [PubMed:11409941 ]
Yang CS, Lee MJ, Chen L: Human salivary tea catechin levels and catechin esterase activities: implication in human cancer prevention studies. Cancer Epidemiol Biomarkers Prev. 1999 Jan;8(1):83-9. [PubMed:9950244 ]
Henning SM, Aronson W, Niu Y, Conde F, Lee NH, Seeram NP, Lee RP, Lu J, Harris DM, Moro A, Hong J, Pak-Shan L, Barnard RJ, Ziaee HG, Csathy G, Go VL, Wang H, Heber D: Tea polyphenols and theaflavins are present in prostate tissue of humans and mice after green and black tea consumption. J Nutr. 2006 Jul;136(7):1839-43. [PubMed:16772446 ]
Lill G, Voit S, Schror K, Weber AA: Complex effects of different green tea catechins on human platelets. FEBS Lett. 2003 Jul 10;546(2-3):265-70. [PubMed:12832052 ]
Murphy KJ, Chronopoulos AK, Singh I, Francis MA, Moriarty H, Pike MJ, Turner AH, Mann NJ, Sinclair AJ: Dietary flavanols and procyanidin oligomers from cocoa (Theobroma cacao) inhibit platelet function. Am J Clin Nutr. 2003 Jun;77(6):1466-73. [PubMed:12791625 ]
Meng X, Lee MJ, Li C, Sheng S, Zhu N, Sang S, Ho CT, Yang CS: Formation and identification of 4'-O-methyl-(-)-epigallocatechin in humans. Drug Metab Dispos. 2001 Jun;29(6):789-93. [PubMed:11353745 ]
Sano A, Yamakoshi J, Tokutake S, Tobe K, Kubota Y, Kikuchi M: Procyanidin B1 is detected in human serum after intake of proanthocyanidin-rich grape seed extract. Biosci Biotechnol Biochem. 2003 May;67(5):1140-3. [PubMed:12834296 ]
Babich H, Krupka ME, Nissim HA, Zuckerbraun HL: Differential in vitro cytotoxicity of (-)-epicatechin gallate (ECG) to cancer and normal cells from the human oral cavity. Toxicol In Vitro. 2005 Mar;19(2):231-42. [PubMed:15649637 ]
Holt RR, Lazarus SA, Sullards MC, Zhu QY, Schramm DD, Hammerstone JF, Fraga CG, Schmitz HH, Keen CL: Procyanidin dimer B2 [epicatechin-(4beta-8)-epicatechin] in human plasma after the consumption of a flavanol-rich cocoa. Am J Clin Nutr. 2002 Oct;76(4):798-804. [PubMed:12324293 ]
Spencer JP, Schroeter H, Crossthwaithe AJ, Kuhnle G, Williams RJ, Rice-Evans C: Contrasting influences of glucuronidation and O-methylation of epicatechin on hydrogen peroxide-induced cell death in neurons and fibroblasts. Free Radic Biol Med. 2001 Nov 1;31(9):1139-46. [PubMed:11677047 ]
DuPont MS, Bennett RN, Mellon FA, Williamson G: Polyphenols from alcoholic apple cider are absorbed, metabolized and excreted by humans. J Nutr. 2002 Feb;132(2):172-5. [PubMed:11823574 ]
Vinson JA, Proch J, Bose P: MegaNatural((R)) Gold Grapeseed Extract: In Vitro Antioxidant and In Vivo Human Supplementation Studies. J Med Food. 2001 Spring;4(1):17-26. [PubMed:12639284 ]
Lhoste EF, Ouriet V, Bruel S, Flinois JP, Brezillon C, Magdalou J, Cheze C, Nugon-Baudon L: The human colonic microflora influences the alterations of xenobiotic-metabolizing enzymes by catechins in male F344 rats. Food Chem Toxicol. 2003 May;41(5):695-702. [PubMed:12659723 ]
Keen CL: Chocolate: food as medicine/medicine as food. J Am Coll Nutr. 2001 Oct;20(5 Suppl):436S-439S; discussion 440S-442S. [PubMed:11603654 ]
Schmidt D, Hakeem Said I, Ohl N, Sharifii M, Cotrell P, Kuhnert N: Investigating the interaction between dietary polyphenols, the SARS CoV-2 spike protein and the ACE-2 receptor. Food Funct. 2022 Jun 23. doi: 10.1039/d2fo00394e. [PubMed:35734946 ]

Showing NP-Card for Epicatechin (NP0000562)

MOL for NP0000562 (Epicatechin)

3D MOL for NP0000562 (Epicatechin)

3D SDF for NP0000562 (Epicatechin)

3D-SDF for NP0000562 (Epicatechin)

PDB for NP0000562 (Epicatechin)

3D PDB for NP0000562 (Epicatechin)

SMILES for NP0000562 (Epicatechin)

INCHI for NP0000562 (Epicatechin)

Structure for NP0000562 (Epicatechin)

3D Structure for NP0000562 (Epicatechin)