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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-02-23 11:52:29 UTC

Update Date

2022-03-07 02:49:11 UTC

HMDB ID

HMDB0001871

Secondary Accession Numbers

HMDB01871

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>
HMDB0001871

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View Stereo Labels

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 Molecular Weight

290.2681

Monoisotopic Molecular Weight

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

490-46-0

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 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	166.887	31661259
DarkChem	[M-H]-	164.032	31661259
AllCCS	[M+H]+	168.382	32859911
AllCCS	[M-H]-	167.258	32859911
DeepCCS	[M+H]+	169.92	30932474
DeepCCS	[M-H]-	167.562	30932474
DeepCCS	[M-2H]-	201.35	30932474
DeepCCS	[M+Na]+	176.578	30932474
AllCCS	[M+H]+	168.4	32859911
AllCCS	[M+H-H2O]+	164.7	32859911
AllCCS	[M+NH4]+	171.8	32859911
AllCCS	[M+Na]+	172.8	32859911
AllCCS	[M-H]-	167.3	32859911
AllCCS	[M+Na-2H]-	166.8	32859911
AllCCS	[M+HCOO]-	166.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.72 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8706 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.28 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	78.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1135.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	209.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	94.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	139.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	71.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	404.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	312.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	560.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	629.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	270.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1004.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	194.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	225.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	505.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	403.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	262.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Epicatechin	O[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C=C1	4436.3	Standard polar	33892256
Epicatechin	O[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C=C1	3029.0	Standard non polar	33892256
Epicatechin	O[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C=C1	3065.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Epicatechin,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC=C(O)C(O)=C1	3049.8	Semi standard non polar	33892256
Epicatechin,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC2=C1C[C@@H](O)[C@@H](C1=CC=C(O)C(O)=C1)O2	3030.9	Semi standard non polar	33892256
Epicatechin,1TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=C2C[C@@H](O)[C@@H](C3=CC=C(O)C(O)=C3)OC2=C1	3091.6	Semi standard non polar	33892256
Epicatechin,1TMS,isomer #4	C[Si](C)(C)OC1=CC([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C1O	3082.9	Semi standard non polar	33892256
Epicatechin,1TMS,isomer #5	C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)C=C1O	3085.4	Semi standard non polar	33892256
Epicatechin,2TMS,isomer #1	C[Si](C)(C)OC1=CC(O)=CC2=C1C[C@@H](O[Si](C)(C)C)[C@@H](C1=CC=C(O)C(O)=C1)O2	2981.9	Semi standard non polar	33892256
Epicatechin,2TMS,isomer #10	C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)C=C1O[Si](C)(C)C	2976.2	Semi standard non polar	33892256
Epicatechin,2TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=C2C[C@@H](O[Si](C)(C)C)[C@@H](C3=CC=C(O)C(O)=C3)OC2=C1	2969.7	Semi standard non polar	33892256
Epicatechin,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O[Si](C)(C)C)C=C1O	3009.1	Semi standard non polar	33892256
Epicatechin,2TMS,isomer #4	C[Si](C)(C)OC1=CC([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O[Si](C)(C)C)=CC=C1O	3012.0	Semi standard non polar	33892256
Epicatechin,2TMS,isomer #5	C[Si](C)(C)OC1=CC2=C(C[C@@H](O)[C@@H](C3=CC=C(O)C(O)=C3)O2)C(O[Si](C)(C)C)=C1	2914.9	Semi standard non polar	33892256
Epicatechin,2TMS,isomer #6	C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C[C@H]2O)C=C1O	2956.2	Semi standard non polar	33892256
Epicatechin,2TMS,isomer #7	C[Si](C)(C)OC1=CC([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C[C@H]2O)=CC=C1O	2959.4	Semi standard non polar	33892256
Epicatechin,2TMS,isomer #8	C[Si](C)(C)OC1=CC(O)=C2C[C@@H](O)[C@@H](C3=CC=C(O[Si](C)(C)C)C(O)=C3)OC2=C1	2992.7	Semi standard non polar	33892256
Epicatechin,2TMS,isomer #9	C[Si](C)(C)OC1=CC(O)=C2C[C@@H](O)[C@@H](C3=CC=C(O)C(O[Si](C)(C)C)=C3)OC2=C1	2987.2	Semi standard non polar	33892256
Epicatechin,3TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C[C@@H](O[Si](C)(C)C)[C@@H](C3=CC=C(O)C(O)=C3)O2)C(O[Si](C)(C)C)=C1	2818.8	Semi standard non polar	33892256
Epicatechin,3TMS,isomer #10	C[Si](C)(C)OC1=CC(O)=C2C[C@@H](O)[C@@H](C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C1	2852.0	Semi standard non polar	33892256
Epicatechin,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C[C@H]2O[Si](C)(C)C)C=C1O	2835.3	Semi standard non polar	33892256
Epicatechin,3TMS,isomer #3	C[Si](C)(C)OC1=CC([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C[C@H]2O[Si](C)(C)C)=CC=C1O	2846.6	Semi standard non polar	33892256
Epicatechin,3TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=C2C[C@@H](O[Si](C)(C)C)[C@@H](C3=CC=C(O[Si](C)(C)C)C(O)=C3)OC2=C1	2802.4	Semi standard non polar	33892256
Epicatechin,3TMS,isomer #5	C[Si](C)(C)OC1=CC(O)=C2C[C@@H](O[Si](C)(C)C)[C@@H](C3=CC=C(O)C(O[Si](C)(C)C)=C3)OC2=C1	2810.0	Semi standard non polar	33892256
Epicatechin,3TMS,isomer #6	C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O[Si](C)(C)C)C=C1O[Si](C)(C)C	2889.8	Semi standard non polar	33892256
Epicatechin,3TMS,isomer #7	C[Si](C)(C)OC1=CC2=C(C[C@@H](O)[C@@H](C3=CC=C(O[Si](C)(C)C)C(O)=C3)O2)C(O[Si](C)(C)C)=C1	2879.4	Semi standard non polar	33892256
Epicatechin,3TMS,isomer #8	C[Si](C)(C)OC1=CC2=C(C[C@@H](O)[C@@H](C3=CC=C(O)C(O[Si](C)(C)C)=C3)O2)C(O[Si](C)(C)C)=C1	2882.9	Semi standard non polar	33892256
Epicatechin,3TMS,isomer #9	C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C[C@H]2O)C=C1O[Si](C)(C)C	2856.8	Semi standard non polar	33892256
Epicatechin,4TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C[C@@H](O[Si](C)(C)C)[C@@H](C3=CC=C(O[Si](C)(C)C)C(O)=C3)O2)C(O[Si](C)(C)C)=C1	2849.5	Semi standard non polar	33892256
Epicatechin,4TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(C[C@@H](O[Si](C)(C)C)[C@@H](C3=CC=C(O)C(O[Si](C)(C)C)=C3)O2)C(O[Si](C)(C)C)=C1	2852.9	Semi standard non polar	33892256
Epicatechin,4TMS,isomer #3	C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C[C@H]2O[Si](C)(C)C)C=C1O[Si](C)(C)C	2821.7	Semi standard non polar	33892256
Epicatechin,4TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=C2C[C@@H](O[Si](C)(C)C)[C@@H](C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C1	2821.4	Semi standard non polar	33892256
Epicatechin,4TMS,isomer #5	C[Si](C)(C)OC1=CC2=C(C[C@@H](O)[C@@H](C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)O2)C(O[Si](C)(C)C)=C1	2896.1	Semi standard non polar	33892256
Epicatechin,5TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C[C@@H](O[Si](C)(C)C)[C@@H](C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)O2)C(O[Si](C)(C)C)=C1	2897.5	Semi standard non polar	33892256
Epicatechin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC=C(O)C(O)=C1	3359.0	Semi standard non polar	33892256
Epicatechin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C[C@@H](O)[C@@H](C1=CC=C(O)C(O)=C1)O2	3331.0	Semi standard non polar	33892256
Epicatechin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C[C@@H](O)[C@@H](C3=CC=C(O)C(O)=C3)OC2=C1	3363.2	Semi standard non polar	33892256
Epicatechin,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C1O	3374.5	Semi standard non polar	33892256
Epicatechin,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)C=C1O	3381.8	Semi standard non polar	33892256
Epicatechin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C1=CC=C(O)C(O)=C1)O2	3518.1	Semi standard non polar	33892256
Epicatechin,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)C=C1O[Si](C)(C)C(C)(C)C	3542.1	Semi standard non polar	33892256
Epicatechin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C3=CC=C(O)C(O)=C3)OC2=C1	3500.6	Semi standard non polar	33892256
Epicatechin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O[Si](C)(C)C(C)(C)C)C=C1O	3575.2	Semi standard non polar	33892256
Epicatechin,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O	3559.2	Semi standard non polar	33892256
Epicatechin,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC2=C(C[C@@H](O)[C@@H](C3=CC=C(O)C(O)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3450.5	Semi standard non polar	33892256
Epicatechin,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2O)C=C1O	3498.3	Semi standard non polar	33892256
Epicatechin,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2O)=CC=C1O	3472.3	Semi standard non polar	33892256
Epicatechin,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C[C@@H](O)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)OC2=C1	3539.2	Semi standard non polar	33892256
Epicatechin,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C[C@@H](O)[C@@H](C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	3504.9	Semi standard non polar	33892256
Epicatechin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C3=CC=C(O)C(O)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3546.6	Semi standard non polar	33892256
Epicatechin,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C[C@@H](O)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	3617.1	Semi standard non polar	33892256
Epicatechin,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2O[Si](C)(C)C(C)(C)C)C=C1O	3600.4	Semi standard non polar	33892256
Epicatechin,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2O[Si](C)(C)C(C)(C)C)=CC=C1O	3593.4	Semi standard non polar	33892256
Epicatechin,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)OC2=C1	3583.6	Semi standard non polar	33892256
Epicatechin,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	3584.1	Semi standard non polar	33892256
Epicatechin,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	3623.8	Semi standard non polar	33892256
Epicatechin,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC2=C(C[C@@H](O)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3659.0	Semi standard non polar	33892256
Epicatechin,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC2=C(C[C@@H](O)[C@@H](C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3627.1	Semi standard non polar	33892256
Epicatechin,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2O)C=C1O[Si](C)(C)C(C)(C)C	3610.5	Semi standard non polar	33892256
Epicatechin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3761.3	Semi standard non polar	33892256
Epicatechin,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3742.8	Semi standard non polar	33892256
Epicatechin,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	3723.2	Semi standard non polar	33892256
Epicatechin,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	3725.7	Semi standard non polar	33892256
Epicatechin,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC2=C(C[C@@H](O)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3782.0	Semi standard non polar	33892256
Epicatechin,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3906.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Epicatechin GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-014i-0649000000-e7a2620a4d8b1c243de3	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Epicatechin GC-EI-TOF (Non-derivatized)	splash10-014i-0649000000-e7a2620a4d8b1c243de3	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Epicatechin GC-EI-TOF (Non-derivatized)	splash10-014i-0749000000-89375330724a4ecb82cf	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epicatechin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0940000000-3790a10ce8b93dcb9236	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epicatechin GC-MS (5 TMS) - 70eV, Positive	splash10-000i-3130069000-ca0968505fc89dd82640	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epicatechin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epicatechin Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000f-1690000000-16c536adc2a6e03c5b4f	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epicatechin Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-000i-1910000000-92d64d3194a12735e531	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epicatechin Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-014i-5900000000-1ec541b64eecd72f3551	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epicatechin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive-QTOF	splash10-0006-0090000000-53e575c7acf970449e84	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epicatechin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-0079-0900000000-1c23cf9e8aa258a986ad	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epicatechin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-052r-1970000000-02212cd1c44e06d5add3	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epicatechin ESI-TOF , Negative-QTOF	splash10-002r-0090060010-fa16cfeadd4bc0a05e53	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epicatechin ESI-TOF 20V, Negative-QTOF	splash10-05bk-0950000000-741428eb8454f83974a0	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epicatechin ESI-TOF 10V, Negative-QTOF	splash10-000i-0090000000-6531ef6ba99afaf52425	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epicatechin ESI-TOF , Negative-QTOF	splash10-000i-0090000000-6531ef6ba99afaf52425	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epicatechin ESI-TOF , Negative-QTOF	splash10-002r-0090060010-fa16cfeadd4bc0a05e53	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epicatechin ESI-TOF 20V, Negative-QTOF	splash10-05bk-0950000000-741428eb8454f83974a0	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epicatechin ESI-TOF 10V, Negative-QTOF	splash10-000i-0090000000-6531ef6ba99afaf52425	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epicatechin ESI-TOF 10V, Negative-QTOF	splash10-000i-0090000000-556ed7e0a7c3d19ecd86	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epicatechin ESI-TOF , Negative-QTOF	splash10-001l-0071900002-461eb0f7b0e90ba28a37	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epicatechin DI-ESI-qTof , Positive-QTOF	splash10-000i-0910000000-536acb5c7ec5ce972a4d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epicatechin DI-ESI-qTof , Negative-QTOF	splash10-0f9j-0970000000-6160314e88b9fecac128	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epicatechin LC-ESI-QTOF , negative-QTOF	splash10-000i-0090000000-faedef1b08ce5b70459b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Epicatechin LC-ESI-QTOF , negative-QTOF	splash10-000j-0290000000-5e7b957db3c3dc34b50c	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicatechin 10V, Positive-QTOF	splash10-0006-0590000000-aff1c3cc94786f87cacf	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicatechin 20V, Positive-QTOF	splash10-000i-0920000000-5e84c0d9207a0a018ab4	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicatechin 40V, Positive-QTOF	splash10-05fr-4900000000-3e525d17e0b05647387a	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicatechin 10V, Negative-QTOF	splash10-000i-0290000000-52e8123f5ed55bc47962	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicatechin 20V, Negative-QTOF	splash10-000i-0940000000-cfcd9b4e416f64a26916	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicatechin 40V, Negative-QTOF	splash10-0a6r-2910000000-be77474275eeee51824b	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Fibroblasts
Intestine
Platelet
Prostate

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.625 +/- 0.198 uM	Adult (>18 years old)	Both	Normal	16076092	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	20809621	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	20809621	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	0.13 +/- 0.20 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 125	16197573	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 125	19671472	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 125	19333587	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 125	19812218	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 125	10725114	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 125	20080030	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 125	12324293	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 125	11530986	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 125	12654472	details
Urine	Detected and Quantified	7.445 +/- 5.022 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0.014 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	27273479	details
Urine	Detected and Quantified	0.0207 +/- 0.0210 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	26814424	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	3.571 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

610247 (Eosinophilic esophagitis)

External Links

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

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1136801

References

Synthesis Reference

Law, Khoon Huat; Das, Nagaratnam P. Production of (-)-epicatechin by Uncaria elliptica callus cultures. Phytochemistry (1989), 28(4), 1099-100.

Material Safety Data Sheet (MSDS)

Download (PDF)

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 ]
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Showing metabocard for Epicatechin (HMDB0001871)

MOL for HMDB0001871 (Epicatechin)

3D MOL for HMDB0001871 (Epicatechin)

3D SDF for HMDB0001871 (Epicatechin)

3D-SDF for HMDB0001871 (Epicatechin)

PDB for HMDB0001871 (Epicatechin)

3D PDB for HMDB0001871 (Epicatechin)

SMILES for HMDB0001871 (Epicatechin)

INCHI for HMDB0001871 (Epicatechin)

Structure for HMDB0001871 (Epicatechin)

3D Structure for HMDB0001871 (Epicatechin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra