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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:13:22 UTC

Update Date

2022-03-07 02:55:34 UTC

HMDB ID

HMDB0037954

Secondary Accession Numbers

HMDB37954

Metabolite Identification

Common Name

(+)-Epicatechin

Description

(+)-Epicatechin, also known as ent-epicatechin, 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 (+)-Epicatechin is found, on average, in the highest concentration within pears (Pyrus communis) (+)-Epicatechin has also been detected, but not quantified in, several different foods, such as lettuces (Lactuca sativa), green tea, apples (Malus pumila), teas (Camellia sinensis), and common buckwheats (Fagopyrum esculentum). This could make (+)-epicatechin a potential biomarker for the consumption of these foods (+)-Epicatechin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on (+)-Epicatechin.

Structure

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

HMDB0037954
     RDKit          3D
(+)-Epicatechin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.3366   -3.3165   -0.0404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5321   -2.1609   -0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0137   -1.0261   -0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1918    0.0962   -0.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7012    1.2291   -1.3388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9595    0.0900   -0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4797   -1.0312    0.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2920   -2.1602    0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2306   -1.0322    1.1293 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5217    0.1661    1.3850 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6986    0.1737    0.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4326   -1.0064    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5551   -1.0391   -0.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9984    0.0885   -1.1041 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1396    0.0573   -1.9174 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2888    1.2502   -0.9428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7137    2.4044   -1.5971 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1583    1.2807   -0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4199    1.3020    1.2655 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0638    2.5518    1.5256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0988    1.2951   -0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2113   -3.9540   -0.8169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9964   -1.0209   -1.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5900    1.2603   -1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9414   -3.0533    1.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7950    0.0650    2.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0854   -1.8794    0.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1386   -1.9486   -0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6796   -0.7761   -2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5210    2.4353   -2.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6724    2.2271   -0.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2762    1.0625    1.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1783    2.9075    2.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6911    2.2282   -0.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3221    1.2341   -0.8800 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  1
 20 33  1  0
 21 34  1  0
 21 35  1  0
M  END


  Mrv1652307201900052D          

 21 23  0  0  0  0            999 V2000
   -2.8635   -0.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8647   -1.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1499   -1.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1518    0.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4367   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4333   -1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7182   -1.5226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0019   -1.1078    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0053   -0.2795    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7250    0.1338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7076    0.1349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4221   -0.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1347    0.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1326    0.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4120    1.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7024    0.9557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8500   -0.2740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8449    1.3774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7134   -1.5184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1494   -2.3539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5779    0.1231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  1 21  1  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3 20  1  0  0  0  0
  3  6  2  0  0  0  0
  5  4  2  0  0  0  0
  5 10  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 19  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  1  0  0  0
 16 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 17  1  0  0  0  0
 13 14  2  0  0  0  0
 14 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037954

> <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-/m0/s1

> <INCHI_KEY>
PFTAWBLQPZVEMU-ZFWWWQNUSA-N

> <FORMULA>
C15H14O6

> <MOLECULAR_WEIGHT>
290.2681

> <EXACT_MASS>
290.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
28.38679947484899

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S)-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>
73.9997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
l-epicatechin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037954
     RDKit          3D
(+)-Epicatechin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.3366   -3.3165   -0.0404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5321   -2.1609   -0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0137   -1.0261   -0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1918    0.0962   -0.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7012    1.2291   -1.3388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9595    0.0900   -0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4797   -1.0312    0.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2920   -2.1602    0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2306   -1.0322    1.1293 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5217    0.1661    1.3850 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6986    0.1737    0.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4326   -1.0064    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5551   -1.0391   -0.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9984    0.0885   -1.1041 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1396    0.0573   -1.9174 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2888    1.2502   -0.9428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7137    2.4044   -1.5971 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1583    1.2807   -0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4199    1.3020    1.2655 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0638    2.5518    1.5256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0988    1.2951   -0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2113   -3.9540   -0.8169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9964   -1.0209   -1.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5900    1.2603   -1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9414   -3.0533    1.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7950    0.0650    2.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0854   -1.8794    0.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1386   -1.9486   -0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6796   -0.7761   -2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5210    2.4353   -2.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6724    2.2271   -0.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2762    1.0625    1.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1783    2.9075    2.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6911    2.2282   -0.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3221    1.2341   -0.8800 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  1
 20 33  1  0
 21 34  1  0
 21 35  1  0
M  END

HEADER    PROTEIN                                 20-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUL-19         0                                  
HETATM    1  C   UNK     0      -5.345  -0.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.347  -2.084   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.013  -2.854   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.017   0.231   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.682  -0.533   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.675  -2.079   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.341  -2.842   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.004  -2.068   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.010  -0.522   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.353   0.250   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.321   0.252   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.655  -0.518   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.985   0.254   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.981   1.796   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.636   2.561   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.311   1.784   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.320  -0.511   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.310   2.571   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.332  -2.834   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -4.012  -4.394   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -6.679   0.230   0.000  0.00  0.00           O+0
CONECT    1    4   21    2                                                  
CONECT    2    1    3                                                       
CONECT    3    2   20    6                                                  
CONECT    4    1    5                                                       
CONECT    5    4   10    6                                                  
CONECT    6    3    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7   19    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    5    9                                                       
CONECT   11    9   16   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   17   14                                                  
CONECT   14   13   18   15                                                  
CONECT   15   14   16                                                       
CONECT   16   11   15                                                       
CONECT   17   13                                                            
CONECT   18   14                                                            
CONECT   19    8                                                            
CONECT   20    3                                                            
CONECT   21    1                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0037954
HETATM    1  O1  UNL     1      -4.337  -3.316  -0.040  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.532  -2.161  -0.061  1.00  0.00           C  
HETATM    3  C2  UNL     1      -4.014  -1.026  -0.693  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.192   0.096  -0.694  1.00  0.00           C  
HETATM    5  O2  UNL     1      -3.701   1.229  -1.339  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.959   0.090  -0.099  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.480  -1.031   0.528  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.292  -2.160   0.535  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.231  -1.032   1.129  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.522   0.166   1.385  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.699   0.174   0.528  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.433  -1.006   0.355  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.555  -1.039  -0.444  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.998   0.089  -1.104  1.00  0.00           C  
HETATM   15  O4  UNL     1       5.140   0.057  -1.917  1.00  0.00           O  
HETATM   16  C12 UNL     1       3.289   1.250  -0.943  1.00  0.00           C  
HETATM   17  O5  UNL     1       3.714   2.404  -1.597  1.00  0.00           O  
HETATM   18  C13 UNL     1       2.158   1.281  -0.137  1.00  0.00           C  
HETATM   19  C14 UNL     1      -0.420   1.302   1.265  1.00  0.00           C  
HETATM   20  O6  UNL     1       0.064   2.552   1.526  1.00  0.00           O  
HETATM   21  C15 UNL     1      -1.099   1.295  -0.108  1.00  0.00           C  
HETATM   22  H1  UNL     1      -4.211  -3.954  -0.817  1.00  0.00           H  
HETATM   23  H2  UNL     1      -4.996  -1.021  -1.168  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.590   1.260  -1.778  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.941  -3.053   1.019  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.795   0.065   2.479  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.085  -1.879   0.868  1.00  0.00           H  
HETATM   28  H7  UNL     1       4.139  -1.949  -0.591  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.680  -0.776  -2.055  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.521   2.435  -2.188  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.672   2.227  -0.068  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.276   1.062   1.978  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.178   2.907   2.418  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.691   2.228  -0.201  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.322   1.234  -0.880  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

HMDB0037954
     RDKit          3D
(+)-Epicatechin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.3366   -3.3165   -0.0404 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5321   -2.1609   -0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0137   -1.0261   -0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1918    0.0962   -0.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7012    1.2291   -1.3388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9595    0.0900   -0.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4797   -1.0312    0.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2920   -2.1602    0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2306   -1.0322    1.1293 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5217    0.1661    1.3850 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6986    0.1737    0.5281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4326   -1.0064    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5551   -1.0391   -0.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9984    0.0885   -1.1041 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1396    0.0573   -1.9174 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2888    1.2502   -0.9428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7137    2.4044   -1.5971 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1583    1.2807   -0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4199    1.3020    1.2655 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0638    2.5518    1.5256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0988    1.2951   -0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2113   -3.9540   -0.8169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9964   -1.0209   -1.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5900    1.2603   -1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9414   -3.0533    1.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7950    0.0650    2.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0854   -1.8794    0.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1386   -1.9486   -0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6796   -0.7761   -2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5210    2.4353   -2.1884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6724    2.2271   -0.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2762    1.0625    1.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1783    2.9075    2.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6911    2.2282   -0.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3221    1.2341   -0.8800 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  1
 20 33  1  0
 21 34  1  0
 21 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S,3S)-3',4',5,7-Tetrahydroxyflavan-3-ol	ChEBI
(2S,3S)-3,3',4',5,7-Pentahydroxyflavan	ChEBI
ent-Epicatechin	ChEBI
(+)-cis-3,3',4',5,7-Pentahydroxyflavan	HMDB
(+)-Epicatechol	HMDB
(2S,3S)-(+)-Epicatechin	HMDB
(2S-cis)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol	HMDB
Catechin C	HMDB
D-Epicatechin	HMDB

Chemical Formula

C₁₅H₁₄O₆

Average Molecular Weight

290.2681

Monoisotopic Molecular Weight

290.07903818

IUPAC Name

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

Traditional Name

l-epicatechin

CAS Registry Number

35323-91-2

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-/m0/s1

InChI Key

PFTAWBLQPZVEMU-ZFWWWQNUSA-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:76125 )
catechin (CHEBI:76125 )
Flavans, Flavanols and Leucoanthocyanidins (C09728 )
Flavan 3-ols (C09728 )
Condensed tannins (Proanthocyanidins) (C09728 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037954)
Cytoplasm (HMDB: HMDB0037954)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037954)

Source

Exogenous

Food

Food (HMDB: HMDB0037954)

Fruit

Pome

Apple (FooDB: FOOD00105)
Pear (FooDB: FOOD00152)
Asian pear (FooDB: FOOD00291)

Tropical fruit

Star fruit (FooDB: FOOD00023)

Cereal and cereal product

Cereal

Common buckwheat (FooDB: FOOD00079)

Vegetable

Leaf vegetable

Lettuce (FooDB: FOOD00095)

Tea

Endogenous

Plant

Plant (HMDB: HMDB0037954)
Poaceae (HMDB: HMDB0037954)

Not Available

Nutrient (HMDB: HMDB0037954)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	235 - 237 °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	28.39 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]+	169.28	31661259
DarkChem	[M-H]-	164.226	31661259
DeepCCS	[M+H]+	169.75	30932474
DeepCCS	[M-H]-	167.392	30932474
DeepCCS	[M-2H]-	201.296	30932474
DeepCCS	[M+Na]+	176.524	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 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
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Epicatechin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0940000000-635a87e4fbbe005b1b88	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
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 LC-ESI-QTOF , negative-QTOF	splash10-052r-0980000000-b5cee6aae1e7952a7d9f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Epicatechin LC-ESI-QTOF , positive-QTOF	splash10-0079-0900000000-9a4ec6a24f97ad3fd9f2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Epicatechin 30V, Positive-QTOF	splash10-00di-0900000000-c152f224fc3c49acdeb5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Epicatechin 10V, Positive-QTOF	splash10-007c-0920000000-91de0a80259cfbc0113b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Epicatechin 30V, Positive-QTOF	splash10-00dr-0900000000-437372b0d194754905ce	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Epicatechin 50V, Positive-QTOF	splash10-0g6r-0900000000-5069537b6f392aae0fe1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Epicatechin 10V, Positive-QTOF	splash10-0006-0590000000-516859cd7060b2bf898b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Epicatechin 50V, Positive-QTOF	splash10-000i-0910000000-7236013988c20252d8c7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Epicatechin 30V, Positive-QTOF	splash10-0079-0900000000-9afe75272afab175f889	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Epicatechin 50V, Positive-QTOF	splash10-01bi-2900000000-56fefff3a8f788f1a1ca	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Epicatechin 6V, Positive-QTOF	splash10-0006-0490000000-1b85894a81aba913bda3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Epicatechin 10V, Positive-QTOF	splash10-0006-0490000000-80c202adef30df74053b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Epicatechin 10V, Positive-QTOF	splash10-000i-0910000000-fd8f0d6d6ee1a117d994	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Epicatechin 6V, Positive-QTOF	splash10-007c-0920000000-ca2ff9eca6136f481a1d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Epicatechin 10V, Positive-QTOF	splash10-0006-0690000000-31f869b582ff052495f7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Epicatechin 10V, Positive-QTOF	splash10-0079-0910000000-7c1c4c01e56414dde318	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Epicatechin 6V, Positive-QTOF	splash10-0006-0590000000-b3372a9dc6a409ae8998	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (+)-Epicatechin 6V, Positive-QTOF	splash10-0079-0900000000-9731a6caadd423aea0a1	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Epicatechin 10V, Positive-QTOF	splash10-0006-0590000000-aff1c3cc94786f87cacf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Epicatechin 20V, Positive-QTOF	splash10-000i-0920000000-5e84c0d9207a0a018ab4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Epicatechin 40V, Positive-QTOF	splash10-05fr-4900000000-3e525d17e0b05647387a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Epicatechin 10V, Negative-QTOF	splash10-000i-0290000000-52e8123f5ed55bc47962	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Epicatechin 20V, Negative-QTOF	splash10-000i-0940000000-cfcd9b4e416f64a26916	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Epicatechin 40V, Negative-QTOF	splash10-0a6r-2910000000-be77474275eeee51824b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Epicatechin 10V, Negative-QTOF	splash10-000i-0090000000-f6afeb92914fea4cf8de	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

182232

PDB ID

Not Available

ChEBI ID

76125

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1680961

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (+)-Epicatechin (HMDB0037954)

MOL for HMDB0037954 ((+)-Epicatechin)

3D MOL for HMDB0037954 ((+)-Epicatechin)

3D SDF for HMDB0037954 ((+)-Epicatechin)

3D-SDF for HMDB0037954 ((+)-Epicatechin)

PDB for HMDB0037954 ((+)-Epicatechin)

3D PDB for HMDB0037954 ((+)-Epicatechin)

SMILES for HMDB0037954 ((+)-Epicatechin)

INCHI for HMDB0037954 ((+)-Epicatechin)

Structure for HMDB0037954 ((+)-Epicatechin)

3D Structure for HMDB0037954 ((+)-Epicatechin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra