MiMeDB: Showing metabocard for Epicatechin (MMDBc0000575)

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

Functional Ontology

Physical Properties

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

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

External Links

References

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:0x00007fb7e07d76a8>

3D MOL for #<Metabolite:0x00007fb7e07d76a8>

3D SDF for #<Metabolite:0x00007fb7e07d76a8>

3D-SDF for #<Metabolite:0x00007fb7e07d76a8>

PDB for #<Metabolite:0x00007fb7e07d76a8>

3D PDB for #<Metabolite:0x00007fb7e07d76a8>

SMILES for #<Metabolite:0x00007fb7e07d76a8>

INCHI for #<Metabolite:0x00007fb7e07d76a8>

Structure for #<Metabolite:0x00007fb7e07d76a8>

3D Structure for #<Metabolite:0x00007fb7e07d76a8>