MiMeDB: Showing metabocard for Epicatechin (MMDBc0000575)

Not Available

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:50:17 UTC

Update Date

2024-09-27 20:33:08 UTC

Metabolite ID

MMDBc0000575

Metabolite 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

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


  Mrv1652309272007282D          

 21 23  0  0  0  0            999 V2000
 9999.8675 9997.3609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0118 9996.5306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.5807 9999.0203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.586210001.0853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.015210000.2572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0119 9999.0144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2974 9998.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2974 9997.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.0118 9997.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2986 9999.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.584210000.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8696 9999.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8696 9999.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.5841 9998.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2986 9999.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4395 9999.0145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.7251 9998.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.7251 9997.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4395 9997.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1539 9997.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.1539 9998.6020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 10  1  0  0  0  0
 11  4  1  0  0  0  0
 10  5  1  0  0  0  0
  9  2  1  0  0  0  0
  7  3  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 20  1  1  6  0  0  0
 21 13  1  6  0  0  0
 17  6  2  0  0  0  0
  9 18  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000575

> <DATABASE_NAME>
MIME

> <SMILES>
O[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C=C1

> <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                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8666.4198661.740   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8661.0898660.190   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8658.4178664.838   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8667.7618668.693   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8670.4288667.147   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8661.0898664.827   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8659.7558664.057   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8659.7558662.517   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8661.0898661.747   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8669.0918666.378   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.7578667.148   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8666.4238666.378   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.4238664.838   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8667.7578664.068   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8669.0918664.838   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8663.7548664.827   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    8662.4208664.057   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8662.4208662.517   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8663.7548661.747   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8665.0878662.517   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8665.0878664.057   0.000  0.00  0.00           C+0
CONECT    1   20                                                            
CONECT    2    9                                                            
CONECT    3    7                                                            
CONECT    4   11                                                            
CONECT    5   10                                                            
CONECT    6    7   17                                                       
CONECT    7    6    8    3                                                  
CONECT    8    7    9                                                       
CONECT    9    8    2   18                                                  
CONECT   10   11   15    5                                                  
CONECT   11   10   12    4                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16   17   21                                                       
CONECT   17   18   16    6                                                  
CONECT   18   17   19    9                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21    1                                                  
CONECT   21   20   16   13                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   46    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

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

Molecular Formula

C₁₅H₁₄O₆

Average Mass

290.2681

Monoisotopic Mass

290.07903818

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

Not Available

SMILES

O[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C=C1

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

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-014i-0649000000-e7a2620a4d8b1c243de3	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0649000000-e7a2620a4d8b1c243de3	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0749000000-89375330724a4ecb82cf	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0940000000-3790a10ce8b93dcb9236	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-000i-3130069000-ca0968505fc89dd82640	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000f-1690000000-16c536adc2a6e03c5b4f	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-1910000000-92d64d3194a12735e531	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-5900000000-1ec541b64eecd72f3551	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive	splash10-0006-0090000000-53e575c7acf970449e84	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0079-0900000000-1c23cf9e8aa258a986ad	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-052r-1970000000-02212cd1c44e06d5add3	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-002r-0090060010-fa16cfeadd4bc0a05e53	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-05bk-0950000000-741428eb8454f83974a0	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-000i-0090000000-6531ef6ba99afaf52425	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0090000000-6531ef6ba99afaf52425	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-002r-0090060010-fa16cfeadd4bc0a05e53	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-05bk-0950000000-741428eb8454f83974a0	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-000i-0090000000-6531ef6ba99afaf52425	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-000i-0090000000-556ed7e0a7c3d19ecd86	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-001l-0071900002-461eb0f7b0e90ba28a37	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-000i-0910000000-536acb5c7ec5ce972a4d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-0f9j-0970000000-6160314e88b9fecac128	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000i-0090000000-faedef1b08ce5b70459b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000j-0290000000-5e7b957db3c3dc34b50c	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0590000000-aff1c3cc94786f87cacf	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0920000000-5e84c0d9207a0a018ab4	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fr-4900000000-3e525d17e0b05647387a	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0290000000-52e8123f5ed55bc47962	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0940000000-cfcd9b4e416f64a26916	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-2910000000-be77474275eeee51824b	2017-07-26	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)		2015-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)		2015-03-12	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Fibroblasts
Intestine
Platelet
Prostate
Urine

Tissue Locations

Fibroblasts
Intestine
Platelet
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Actinobacteria	1	Human ; Human mucosa; Human supragingival plaque; Human saliva; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	1	Human ; Human mucosa	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Food			FooDB	34893796
Food	Cocoa products	Theobroma cacao	FooDB	34893796
Food	Cocoa products	Theobroma cacao	FooDB	34893796
Food	Cocoa products	Theobroma cacao	FooDB	34893796
Food	Cocoa products	Theobroma cacao	FooDB	34893796
Food	Cocoa products	Theobroma cacao	FooDB	34893796
Food	Cocoa products	Theobroma cacao	FooDB	34893796
Plant	Fruit	Cydonia oblonga	FooDB	34893796
Plant	Fruit	Ribes nigrum	FooDB	34893796
Plant		Rheum rhabarbarum	FooDB	34893796
Plant		Vaccinium	FooDB	34893796
Plant	Fruit	Malus pumila	FooDB	34893796
Plant	Fruit	Ribes nigrum	FooDB	34893796
Plant	Nut	Castanea sativa	FooDB	34893796
Plant		Apium graveolens	FooDB	34893796
Plant	Fruit	Pyrus communis	FooDB	34893796
Plant	Fruit	Cucumis sativus	FooDB	34893796
Plant	Seed	Phaseolus vulgaris	FooDB	34893796
Plant	Fruit	Malus pumila	FooDB	34893796
Plant		Fragaria x ananassa	FooDB	34893796
Plant		Fragaria x ananassa	FooDB	34893796
Plant	Fruit	Prunus cerasus	FooDB	34893796
Plant	Fruit	Pyrus communis	FooDB	34893796
Plant		Solanum tuberosum	FooDB	34893796
Plant		Raphanus sativus	FooDB	34893796
Plant		Prunus dulcis	FooDB	34893796
Plant		Solanum lycopersicum	FooDB	34893796
Plant	Fruit	Vaccinium macrocarpon	FooDB	34893796
Plant		Brassica ruvo	FooDB	34893796
Plant		Brassica oleracea var. gemmifera	FooDB	34893796
Plant		Pinus edulis	FooDB	34893796
Plant		Pyrus communis	FooDB	34893796
Plant		Arachis hypogaea	FooDB	34893796
Plant		Allium	FooDB	34893796
Plant	Fruit	Malus pumila	FooDB	34893796
Plant	Fruit	Rubus arcticus	FooDB	34893796
Plant		Corylus	FooDB	34893796
Plant		Mangifera indica	FooDB	34893796
Plant	Fruit	Malus pumila	FooDB	34893796
Plant	Juice	Citrus x paradisi	FooDB	34893796
Plant		Actinidia chinensis	FooDB	34893796
Plant		Actinidia chinensis	FooDB	34893796
Plant	Fruit	Phoenix dactylifera	FooDB	34893796
Plant	Juice	Vitis rotundifolia	FooDB	34893796
Plant		Vitis	FooDB	34893796
Plant		Vitis	FooDB	34893796
Plant		Vitis	FooDB	34893796
Plant		Lactuca sativa	FooDB	34893796
Plant		Vitis	FooDB	34893796
Plant	Fruit	Malus pumila	FooDB	34893796
Plant	Fruit	Ribes rubrum	FooDB	34893796
Plant		Cynara scolymus	FooDB	34893796
Plant		Prunus persica	FooDB	34893796
Plant		Citrus x paradisi	FooDB	34893796
Plant		Prunus persica	FooDB	34893796
Plant		Agaricus bisporus	FooDB	34893796
Plant		Brassica oleracea var. botrytis	FooDB	34893796
Plant	Fruit	Ribes rubrum	FooDB	34893796
Plant	Fruit	Ficus carica	FooDB	34893796
Plant	Seed	Glycine max	FooDB	34893796
Plant		Ziziphus zizyphus	FooDB	34893796
Plant		Allium	FooDB	34893796
Plant	Fruit	Punica granatum	FooDB	34893796
Plant		Lens culinaris	FooDB	34893796
Plant		Lactuca sativa	FooDB	34893796
Plant		Pisum sativum	FooDB	34893796
Plant		Juglans regia	FooDB	34893796
Plant	Fruit	Rubus chamaemorus	FooDB	34893796
Plant	Root	Beta vulgaris	FooDB	34893796
Plant		Punica granatum	FooDB	34893796
Plant		Pistacia vera	FooDB	34893796
Plant	Seed	Phaseolus vulgaris	FooDB	34893796
Plant		Brassica oleracea	FooDB	34893796
Plant	Fruit	Annona reticulata	FooDB	34893796
Plant		Carya illinoinensis	FooDB	34893796
Plant	Fruit	Citrus sinensis	FooDB	34893796
Plant		Capsicum annuum	FooDB	34893796
Plant	Fruit	Vaccinium	FooDB	34893796
Plant	Fruit	Diospyros virginiana	FooDB	34893796
Plant		Malus pumila	FooDB	34893796
Plant	Fruit	Persea americana	FooDB	34893796
Plant	Root	Daucus carota ssp. sativus	FooDB	34893796
Plant		Brassica rapa	FooDB	34893796
Plant	Seed	Vitis	FooDB	34893796
Plant	Bean	Phaseolus vulgaris	FooDB	34893796
Plant	Fruit	Vaccinium	FooDB	34893796
Plant		Cucumis melo	FooDB	34893796
Plant		Ananas comosus	FooDB	34893796
Plant	Bulb and lower leaf-portion	Allium ampeloprasum	FooDB	34893796
Plant		Cucumis melo	FooDB	34893796
Plant		Cichorium intybus	FooDB	34893796
Plant	Seed	Cicer arietinum	FooDB	34893796
Plant		Prunus	FooDB	34893796
Plant		Prunus	FooDB	34893796
Plant		Macadamia	FooDB	34893796
Plant		Musa acuminata	FooDB	34893796
Plant	Fruit	Ribes uva-crispa	FooDB	34893796
Plant		Citrus sinensis	FooDB	34893796
Plant	Fruit	Prunus avium	FooDB	34893796
Plant	Seed	Pisum sativum	FooDB	34893796
Plant		Prunus domestica	FooDB	34893796
Plant		Prunus domestica	FooDB	34893796
Plant	Fruit	Prunus armeniaca	FooDB	34893796
Plant	Seed	Anacardium occidentale	FooDB	DUKE
Plant		Citrullus lanatus	FooDB	34893796
Plant	Fruit	Cucurbita	FooDB	34893796
Plant		Theobroma cacao	FooDB	34893796
Plant		Bertholletia excelsa	FooDB	34893796
Plant		Prunus persica var. nucipersica	FooDB	34893796
Plant		Prunus persica var. nucipersica	FooDB	34893796
Plant	Fruit	Malus pumila	FooDB	34893796
Plant	Fruit	Vaccinium vitis-idaea	FooDB	34893796
Plant		Anacardium occidentale	FooDB	34893796
Plant	Fruit	Malus pumila	FooDB	34893796
Plant	Fruit	Vitis	FooDB	34893796
Plant	Seed	Vicia faba	FooDB	34893796
Plant	Seed	Vicia faba	FooDB	34893796
Plant	Fruit	Malus pumila	FooDB	34893796
Plant		Daucus carota ssp. sativus	FooDB	34893796
Plant	Fruit	Malus pumila	FooDB	34893796
Plant		Mespilus germanica	FooDB	34893796
Plant		Brassica oleracea var. italica	FooDB	34893796
Plant		Vitis vinifera	FooDB	34893796
Plant		Solanum melongena	FooDB	34893796
Plant	Fruit	Vitis	FooDB	34893796
Plant		Cichorium endivia	FooDB	34893796
Plant	Fruit	Malus pumila	FooDB	34893796

Source Type	Activity	Data Source	Reference
Not Available	Antioxidant	U.S. Environmental Protection Agency	CompTox
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	0.014		umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	27273479
Human Urine	Detected and Quantified	0.0207	0.0210	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	26814424
Human Urine	Detected and Quantified	0.13	0.20	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Blood	Detected and Quantified	0.625	0.198	uM	Adult (>18 years old)	Both	Normal	HMDB	16076092
Human Urine	Detected and Quantified	3.571		umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	7.445	5.022	umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Fibroblasts	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified				Adult (>18 years old)	Male	Normal	HMDB	20809621
Human Feces	Detected but not Quantified				Adult (>18 years old)	Male	Normal	HMDB	20809621
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0001871

DrugBank ID

DB12039

Phenol Explorer Compound ID

FooDB 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

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 ]
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 ]
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. doi: 10.1021/tx0002536. [PubMed:11409941 ]
Keen CL: Chocolate: food as medicine/medicine as food. J Am Coll Nutr. 2001 Oct;20(5 Suppl):436S-439S; discussion 440S-442S. doi: 10.1080/07315724.2001.10719181. [PubMed:11603654 ]
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. doi: 10.1016/s0891-5849(01)00704-3. [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. doi: 10.1093/jn/132.2.172. [PubMed:11823574 ]
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. doi: 10.1093/ajcn/76.4.798. [PubMed:12324293 ]
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. doi: 10.1089/10966200152053677. [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. doi: 10.1016/s0278-6915(03)00010-3. [PubMed:12659723 ]
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. doi: 10.1093/ajcn/77.6.1466. [PubMed:12791625 ]
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. doi: 10.1016/s0014-5793(03)00599-4. [PubMed:12832052 ]
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. doi: 10.1271/bbb.67.1140. [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. doi: 10.1016/j.tiv.2004.09.001. [PubMed:15649637 ]
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. doi: 10.1093/jn/136.7.1839. [PubMed:16772446 ]

Showing metabocard for Epicatechin (MMDBc0000575)

MOL for #<Metabolite:0x00007fdb486c45a0>

3D MOL for #<Metabolite:0x00007fdb486c45a0>

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Structure for #<Metabolite:0x00007fdb486c45a0>

3D Structure for #<Metabolite:0x00007fdb486c45a0>