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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:14 UTC

Update Date

2022-03-07 02:52:42 UTC

HMDB ID

HMDB0030822

Secondary Accession Numbers

HMDB30822

Metabolite Identification

Common Name

(-)-Epiafzelechin

Description

(-)-Epiafzelechin belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4. Thus, (-)-epiafzelechin is considered to be a flavonoid (-)-Epiafzelechin is found, on average, in the highest concentration within a few different foods, such as teas (Camellia sinensis), red tea, and herbal tea and in a lower concentration in green tea and black tea (-)-Epiafzelechin has also been detected, but not quantified in, several different foods, such as hibiscus teas (Hibiscus sabbariffa), green bell peppers (Capsicum annuum), muscadine grapes (Vitis rotundifolia), white mustards (Sinapis alba), and black plums (Syzygium cumini). This could make (-)-epiafzelechin a potential biomarker for the consumption of these foods (-)-Epiafzelechin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on (-)-Epiafzelechin.

Structure

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

HMDB0030822
     RDKit          3D
(-)-Epiafzelechin
 34 36  0  0  0  0  0  0  0  0999 V2000
   -5.8932    1.1867   -0.0968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5656    0.7960   -0.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1407   -0.4393    0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8310   -0.8743    0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9019   -0.0691   -0.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4889   -0.4467   -0.7943 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3120    0.6416   -0.4404 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6322    0.5911   -0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4007    1.7073    0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7379    1.6505    0.4407 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5028    2.8074    0.5858 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2622    0.3924    0.6538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4910   -0.7650    0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1432   -1.9658    0.7518 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1811   -0.6703    0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3701   -1.8819   -0.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1054   -1.6302    0.0548 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4391   -1.4395    1.4009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3218    1.1689   -1.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6261    1.6000   -0.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2041    1.6872    0.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8441   -1.1004    0.6585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4987   -1.8407    0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3805   -0.7525   -1.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9533    2.6865   -0.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9885    3.1211   -0.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3153    0.3379    0.9448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323   -2.8194    0.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6728   -2.4567   -0.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6178   -2.5622    0.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6186   -2.5253   -0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8135   -0.5280    1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5849    1.8237   -1.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9549    2.5693   -1.2368 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 17  6  1  0
 15  8  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  6
  9 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  6
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END


  Mrv1652309042000372D          

 20 22  0  0  0  0            999 V2000
    1.7854    1.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    1.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7854   -0.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5004    0.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5004    1.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2154    1.4849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7868   -2.2275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7868   -1.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5004   -0.9901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5004   -0.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2154    0.2475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7868    0.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.9901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3581   -1.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3568   -0.9901    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3568   -0.1651    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3581    0.2475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.4025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 15  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 20  1  6  0  0  0
 18 19  1  0  0  0  0
 18  3  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0030822

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2/t13-,15-/m1/s1

> <INCHI_KEY>
RSYUFYQTACJFML-UKRRQHHQSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.2687

> <EXACT_MASS>
274.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.512347734652174

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.29

> <JCHEM_LOGP>
2.098672337

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.732353999322413

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.149760394668172

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2843440587393635

> <JCHEM_POLAR_SURFACE_AREA>
90.15

> <JCHEM_REFRACTIVITY>
72.01880000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
epiafzelechin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030822
     RDKit          3D
(-)-Epiafzelechin
 34 36  0  0  0  0  0  0  0  0999 V2000
   -5.8932    1.1867   -0.0968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5656    0.7960   -0.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1407   -0.4393    0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8310   -0.8743    0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9019   -0.0691   -0.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4889   -0.4467   -0.7943 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3120    0.6416   -0.4404 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6322    0.5911   -0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4007    1.7073    0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7379    1.6505    0.4407 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5028    2.8074    0.5858 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2622    0.3924    0.6538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4910   -0.7650    0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1432   -1.9658    0.7518 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1811   -0.6703    0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3701   -1.8819   -0.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1054   -1.6302    0.0548 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4391   -1.4395    1.4009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3218    1.1689   -1.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6261    1.6000   -0.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2041    1.6872    0.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8441   -1.1004    0.6585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4987   -1.8407    0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3805   -0.7525   -1.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9533    2.6865   -0.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9885    3.1211   -0.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3153    0.3379    0.9448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323   -2.8194    0.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6728   -2.4567   -0.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6178   -2.5622    0.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6186   -2.5253   -0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8135   -0.5280    1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5849    1.8237   -1.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9549    2.5693   -1.2368 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 17  6  1  0
 15  8  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  6
  9 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  6
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0       3.333   2.772   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.001   2.002   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.001   0.462   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.333  -0.308   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.667   0.462   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.667   2.002   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.002   2.772   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -3.335  -4.158   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.335  -2.618   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.667  -1.848   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.667  -0.308   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -6.002   0.462   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.335   0.462   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.001  -0.308   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.001  -1.848   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.668  -2.618   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.666  -1.848   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.666  -0.308   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.668   0.462   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.001  -2.618   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6                                                            
CONECT    8    9                                                            
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15    9   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19    3                                                  
CONECT   19   14   18                                                       
CONECT   20   17                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0030822
HETATM    1  O1  UNL     1      -5.893   1.187  -0.097  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.566   0.796  -0.273  1.00  0.00           C  
HETATM    3  C2  UNL     1      -4.141  -0.439   0.173  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.831  -0.874   0.021  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.902  -0.069  -0.590  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.489  -0.447  -0.794  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.312   0.642  -0.440  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.632   0.591  -0.077  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.401   1.707   0.072  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.738   1.651   0.441  1.00  0.00           C  
HETATM   11  O3  UNL     1       4.503   2.807   0.586  1.00  0.00           O  
HETATM   12  C9  UNL     1       4.262   0.392   0.654  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.491  -0.765   0.507  1.00  0.00           C  
HETATM   14  O4  UNL     1       4.143  -1.966   0.752  1.00  0.00           O  
HETATM   15  C11 UNL     1       2.181  -0.670   0.143  1.00  0.00           C  
HETATM   16  C12 UNL     1       1.370  -1.882  -0.011  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.105  -1.630   0.055  1.00  0.00           C  
HETATM   18  O5  UNL     1      -0.439  -1.440   1.401  1.00  0.00           O  
HETATM   19  C14 UNL     1      -2.322   1.169  -1.038  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.626   1.600  -0.886  1.00  0.00           C  
HETATM   21  H1  UNL     1      -6.204   1.687   0.743  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.844  -1.100   0.658  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.499  -1.841   0.370  1.00  0.00           H  
HETATM   24  H4  UNL     1      -0.381  -0.753  -1.855  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.953   2.686  -0.105  1.00  0.00           H  
HETATM   26  H6  UNL     1       4.989   3.121  -0.266  1.00  0.00           H  
HETATM   27  H7  UNL     1       5.315   0.338   0.945  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.632  -2.819   0.659  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.673  -2.457  -0.925  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.618  -2.562   0.852  1.00  0.00           H  
HETATM   31  H11 UNL     1      -0.619  -2.525  -0.375  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.814  -0.528   1.466  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.585   1.824  -1.529  1.00  0.00           H  
HETATM   34  H14 UNL     1      -3.955   2.569  -1.237  1.00  0.00           H  
CONECT    1    2   21
CONECT    2    3    3   20
CONECT    3    4   22
CONECT    4    5    5   23
CONECT    5    6   19
CONECT    6    7   17   24
CONECT    7    8
CONECT    8    9    9   15
CONECT    9   10   25
CONECT   10   11   12   12
CONECT   11   26
CONECT   12   13   27
CONECT   13   14   15   15
CONECT   14   28
CONECT   15   16
CONECT   16   17   29   30
CONECT   17   18   31
CONECT   18   32
CONECT   19   20   20   33
CONECT   20   34
END

HMDB0030822
     RDKit          3D
(-)-Epiafzelechin
 34 36  0  0  0  0  0  0  0  0999 V2000
   -5.8932    1.1867   -0.0968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5656    0.7960   -0.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1407   -0.4393    0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8310   -0.8743    0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9019   -0.0691   -0.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4889   -0.4467   -0.7943 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3120    0.6416   -0.4404 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6322    0.5911   -0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4007    1.7073    0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7379    1.6505    0.4407 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5028    2.8074    0.5858 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2622    0.3924    0.6538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4910   -0.7650    0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1432   -1.9658    0.7518 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1811   -0.6703    0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3701   -1.8819   -0.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1054   -1.6302    0.0548 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4391   -1.4395    1.4009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3218    1.1689   -1.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6261    1.6000   -0.8860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2041    1.6872    0.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8441   -1.1004    0.6585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4987   -1.8407    0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3805   -0.7525   -1.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9533    2.6865   -0.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9885    3.1211   -0.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3153    0.3379    0.9448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323   -2.8194    0.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6728   -2.4567   -0.9249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6178   -2.5622    0.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6186   -2.5253   -0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8135   -0.5280    1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5849    1.8237   -1.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9549    2.5693   -1.2368 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 17  6  1  0
 15  8  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  6
  9 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  6
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2R,3R)-Epiafzelechin	ChEBI
Epi-afzelechin	ChEBI
Epiafzelechin	MeSH

Chemical Formula

C₁₅H₁₄O₅

Average Molecular Weight

274.2687

Monoisotopic Molecular Weight

274.084123558

IUPAC Name

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

Traditional Name

epiafzelechin

CAS Registry Number

24808-04-6

SMILES

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

InChI Identifier

InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2/t13-,15-/m1/s1

InChI Key

RSYUFYQTACJFML-UKRRQHHQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavan-3-ols

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

catechin (CHEBI:31028 )
Flavan 3-ols (C12128 )
Flavans, Flavanols and Leucoanthocyanidins (LMPK12020036 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030822)
Cytoplasm (HMDB: HMDB0030822)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030822)

Source

Endogenous

Endogenous (HMDB: HMDB0030822)

Plant

Plant (HMDB: HMDB0030822)

Exogenous

Food

Food (HMDB: HMDB0030822)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Vegetable

Cabbage

Onion-family vegetable

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Fruits (FooDB: FOOD00871)

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)

Cereal and cereal product

Cereal

Cereal product

Pasta (FooDB: FOOD00273)
Bulgur (FooDB: FOOD00741)
Semolina (FooDB: FOOD00745)
Flour (FooDB: FOOD00799)

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Soy sauce (FooDB: FOOD00694)
Miso (FooDB: FOOD00695)
Tofu (FooDB: FOOD00696)
Soy milk (FooDB: FOOD00736)
Soy cream (FooDB: FOOD00784)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Dish

Other dish

Taco shell (FooDB: FOOD00991)
Tostada shell (FooDB: FOOD00992)

Exogenous (HMDB: HMDB0030822)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Flavonoid Biosynthesis (PathBank: SMP0012021)

Cyclooxygenase 1 inhibitor (HMDB: HMDB0030822)
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor (HMDB: HMDB0030822)

Enzyme inhibitor

Cyclooxygenase inhibitor (HMDB: HMDB0030822)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	240 - 243 °C	Not Available
Boiling Point	583.40 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	8200 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.090 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.46 g/L	ALOGPS
logP	1.29	ALOGPS
logP	2.1	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.15	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	90.15 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.02 m³·mol⁻¹	ChemAxon
Polarizability	27.51 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]+	163.962	31661259
DarkChem	[M-H]-	167.034	31661259
DeepCCS	[M+H]+	159.793	30932474
DeepCCS	[M-H]-	157.435	30932474
DeepCCS	[M-2H]-	191.208	30932474
DeepCCS	[M+Na]+	166.435	30932474
AllCCS	[M+H]+	165.0	32859911
AllCCS	[M+H-H2O]+	161.2	32859911
AllCCS	[M+NH4]+	168.6	32859911
AllCCS	[M+Na]+	169.6	32859911
AllCCS	[M-H]-	164.8	32859911
AllCCS	[M+Na-2H]-	164.3	32859911
AllCCS	[M+HCOO]-	164.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(-)-Epiafzelechin	O[C@@H]1CC2=C(O[C@@H]1C1=CC=C(O)C=C1)C=C(O)C=C2O	4218.7	Standard polar	33892256
(-)-Epiafzelechin	O[C@@H]1CC2=C(O[C@@H]1C1=CC=C(O)C=C1)C=C(O)C=C2O	2898.2	Standard non polar	33892256
(-)-Epiafzelechin	O[C@@H]1CC2=C(O[C@@H]1C1=CC=C(O)C=C1)C=C(O)C=C2O	2962.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(-)-Epiafzelechin,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=C1	2832.3	Semi standard non polar	33892256
(-)-Epiafzelechin,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)C=C1	2865.9	Semi standard non polar	33892256
(-)-Epiafzelechin,1TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=C2C[C@@H](O)[C@@H](C3=CC=C(O)C=C3)OC2=C1	2866.9	Semi standard non polar	33892256
(-)-Epiafzelechin,1TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=CC2=C1C[C@@H](O)[C@@H](C1=CC=C(O)C=C1)O2	2850.2	Semi standard non polar	33892256
(-)-Epiafzelechin,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=C1)O2	2821.2	Semi standard non polar	33892256
(-)-Epiafzelechin,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=C3)OC2=C1	2825.3	Semi standard non polar	33892256
(-)-Epiafzelechin,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=C1	2813.2	Semi standard non polar	33892256
(-)-Epiafzelechin,2TMS,isomer #4	C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O)=C3C[C@H]2O)C=C1	2788.8	Semi standard non polar	33892256
(-)-Epiafzelechin,2TMS,isomer #5	C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O[Si](C)(C)C)=C3C[C@H]2O)C=C1	2780.7	Semi standard non polar	33892256
(-)-Epiafzelechin,2TMS,isomer #6	C[Si](C)(C)OC1=CC2=C(C[C@@H](O)[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C)=C1	2798.2	Semi standard non polar	33892256
(-)-Epiafzelechin,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=C3)O2)C(O[Si](C)(C)C)=C1	2700.8	Semi standard non polar	33892256
(-)-Epiafzelechin,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=C1	2702.4	Semi standard non polar	33892256
(-)-Epiafzelechin,3TMS,isomer #3	C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O)=C3C[C@H]2O[Si](C)(C)C)C=C1	2674.7	Semi standard non polar	33892256
(-)-Epiafzelechin,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C[C@H]2O)C=C1	2776.5	Semi standard non polar	33892256
(-)-Epiafzelechin,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C[C@H]2O[Si](C)(C)C)C=C1	2742.7	Semi standard non polar	33892256
(-)-Epiafzelechin,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=C1	3130.2	Semi standard non polar	33892256
(-)-Epiafzelechin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)C=C1	3142.0	Semi standard non polar	33892256
(-)-Epiafzelechin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C[C@@H](O)[C@@H](C3=CC=C(O)C=C3)OC2=C1	3135.4	Semi standard non polar	33892256
(-)-Epiafzelechin,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C[C@@H](O)[C@@H](C1=CC=C(O)C=C1)O2	3108.7	Semi standard non polar	33892256
(-)-Epiafzelechin,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=C1)O2	3352.6	Semi standard non polar	33892256
(-)-Epiafzelechin,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=C3)OC2=C1	3343.0	Semi standard non polar	33892256
(-)-Epiafzelechin,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=C1	3361.9	Semi standard non polar	33892256
(-)-Epiafzelechin,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C[C@H]2O)C=C1	3356.8	Semi standard non polar	33892256
(-)-Epiafzelechin,2TBDMS,isomer #5	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=C1	3325.2	Semi standard non polar	33892256
(-)-Epiafzelechin,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC2=C(C[C@@H](O)[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3311.4	Semi standard non polar	33892256
(-)-Epiafzelechin,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=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3414.8	Semi standard non polar	33892256
(-)-Epiafzelechin,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=C1	3458.1	Semi standard non polar	33892256
(-)-Epiafzelechin,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C[C@H]2O[Si](C)(C)C(C)(C)C)C=C1	3442.9	Semi standard non polar	33892256
(-)-Epiafzelechin,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2O)C=C1	3527.3	Semi standard non polar	33892256
(-)-Epiafzelechin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C[C@H]2O[Si](C)(C)C(C)(C)C)C=C1	3621.6	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 - (-)-Epiafzelechin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1970000000-97a69c7a45c624cc5456	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Epiafzelechin GC-MS (4 TMS) - 70eV, Positive	splash10-002b-3700890000-ad3a8c90f22f6dcef7bc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Epiafzelechin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-Epiafzelechin 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 - (-)-Epiafzelechin Linear Ion Trap , negative-QTOF	splash10-004r-0690000000-4da2a1e1b8ae2d109c32	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Epiafzelechin Linear Ion Trap , negative-QTOF	splash10-004r-0690000000-3dda57eb8519237ff1d3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Epiafzelechin Linear Ion Trap , negative-QTOF	splash10-004r-0690000000-90138410b48eec3cdf8b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Epiafzelechin Linear Ion Trap , positive-QTOF	splash10-000i-0900000000-197f43a10026114cf6e7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Epiafzelechin 40V, Negative-QTOF	splash10-0a59-0910000000-4f271083ff1af2b4a646	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Epiafzelechin 20V, Negative-QTOF	splash10-000i-0930000000-fd8af365cba78f21a442	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Epiafzelechin 10V, Negative-QTOF	splash10-00di-0490000000-d1cb482bc9fba5c1c77c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Epiafzelechin 40V, Positive-QTOF	splash10-0a4i-0900000000-0931dca1f9eede095b91	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Epiafzelechin 10V, Positive-QTOF	splash10-000j-0910000000-62c438a216915a5cb1cc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (-)-Epiafzelechin 20V, Positive-QTOF	splash10-000i-0900000000-f191f6a8bfb1fdd83316	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Epiafzelechin 10V, Positive-QTOF	splash10-004i-0490000000-102c0099b32eb6cf1c1b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Epiafzelechin 20V, Positive-QTOF	splash10-000i-0920000000-16e90c91e06078017d08	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Epiafzelechin 40V, Positive-QTOF	splash10-05fr-4900000000-1aa083295b52d9560bf8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Epiafzelechin 10V, Negative-QTOF	splash10-00di-0190000000-3f6f215ea99c3e0e4777	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Epiafzelechin 20V, Negative-QTOF	splash10-0079-0940000000-10a1d2bf91d220a561c9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Epiafzelechin 40V, Negative-QTOF	splash10-0a6r-3910000000-d6da6b34ec8094f8de55	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Epiafzelechin 10V, Negative-QTOF	splash10-00di-0190000000-481c391516faccc36069	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Epiafzelechin 20V, Negative-QTOF	splash10-05g0-0970000000-dcc4eab79179a249d464	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Epiafzelechin 40V, Negative-QTOF	splash10-009f-4940000000-776437a8382970f7d1c2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Epiafzelechin 10V, Positive-QTOF	splash10-004i-0090000000-5b1317024b148033f6f6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Epiafzelechin 20V, Positive-QTOF	splash10-004r-0970000000-43adfba1cc7d810c20a9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Epiafzelechin 40V, Positive-QTOF	splash10-0a4r-2920000000-8465db94f8820d798074	2021-09-24	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

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443639

PDB ID

Not Available

ChEBI ID

31028

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1388821

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Pesca MS, Dal Piaz F, Sanogo R, Vassallo A, Bruzual de Abreu M, Rapisarda A, Germano MP, Certo G, De Falco S, De Tommasi N, Braca A: Bioassay-guided isolation of proanthocyanidins with antiangiogenic activities. J Nat Prod. 2013 Jan 25;76(1):29-35. doi: 10.1021/np300614u. Epub 2012 Dec 26. [PubMed:23268742 ]
Xu X, Xie H, Wang Y, Wei X: A-type proanthocyanidins from lychee seeds and their antioxidant and antiviral activities. J Agric Food Chem. 2010 Nov 24;58(22):11667-72. doi: 10.1021/jf1033202. Epub 2010 Oct 22. [PubMed:20964424 ]
Bicker J, Petereit F, Hensel A: Proanthocyanidins and a phloroglucinol derivative from Rumex acetosa L. Fitoterapia. 2009 Dec;80(8):483-95. doi: 10.1016/j.fitote.2009.08.015. Epub 2009 Aug 18. [PubMed:19695312 ]
Zhang HM, Wang CF, Shen SM, Wang GL, Liu P, Liu ZM, Wang YY, Du SS, Liu ZL, Deng ZW: Antioxidant phenolic compounds from Pu-erh tea. Molecules. 2012 Nov 27;17(12):14037-45. doi: 10.3390/molecules171214037. [PubMed:23187287 ]
Yano T, Ohmori K, Takahashi H, Kusumi T, Suzuki K: Unified approach to catechin hetero-oligomers: first total synthesis of trimer EZ-EG-CA isolated from Ziziphus jujuba. Org Biomol Chem. 2012 Oct 14;10(38):7685-8. doi: 10.1039/c2ob26337h. [PubMed:22930202 ]
Savitri Kumar N, Maduwantha B Wijekoon WM, Kumar V, Nimal Punyasiri PA, Sarath B Abeysinghe I: Separation of proanthocyanidins isolated from tea leaves using high-speed counter-current chromatography. J Chromatogr A. 2009 May 8;1216(19):4295-302. doi: 10.1016/j.chroma.2008.12.025. Epub 2008 Dec 24. [PubMed:19136115 ]
Kpegba K, Agbonon A, Petrovic AG, Amouzou E, Gbeassor M, Proni G, Nesnas N: Epiafzelechin from the root bark of Cassia sieberiana: detection by DART mass spectrometry, spectroscopic characterization, and antioxidant properties. J Nat Prod. 2011 Mar 25;74(3):455-9. doi: 10.1021/np100090e. Epub 2010 Nov 11. [PubMed:21070009 ]
Seccon A, Rosa DW, Freitas RA, Biavatti MW, Creczynski-Pasa TB: Antioxidant activity and low cytotoxicity of extracts and isolated compounds from Araucaria angustifolia dead bark. Redox Rep. 2010;15(6):234-42. doi: 10.1179/135100010X12826446921789. [PubMed:21208522 ]
Su J, Wu Z, Shen Y, Liu R, Zhang C, Li H, Zhang W: Flavonoids from Daphne giraldii Nitsche. Nat Prod Res. 2008;22(15):1355-8. doi: 10.1080/14786410701768196. [PubMed:19023794 ]
Liang YH, Ye M, Yang WZ, Qiao X, Wang Q, Yang HJ, Wang XL, Guo DA: Flavan-3-ols from the rhizomes of Drynaria fortunei. Phytochemistry. 2011 Oct;72(14-15):1876-82. doi: 10.1016/j.phytochem.2011.05.011. Epub 2011 Jul 5. [PubMed:21737107 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (-)-Epiafzelechin (HMDB0030822)

MOL for HMDB0030822 ((-)-Epiafzelechin)

3D MOL for HMDB0030822 ((-)-Epiafzelechin)

3D SDF for HMDB0030822 ((-)-Epiafzelechin)

3D-SDF for HMDB0030822 ((-)-Epiafzelechin)

PDB for HMDB0030822 ((-)-Epiafzelechin)

3D PDB for HMDB0030822 ((-)-Epiafzelechin)

SMILES for HMDB0030822 ((-)-Epiafzelechin)

INCHI for HMDB0030822 ((-)-Epiafzelechin)

Structure for HMDB0030822 ((-)-Epiafzelechin)

3D Structure for HMDB0030822 ((-)-Epiafzelechin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra