MiMeDB: Showing metabocard for Ellagic acid (MMDBc0005328)

Not Available

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 22:57:30 UTC

Update Date

2024-09-27 19:54:37 UTC

Metabolite ID

MMDBc0005328

Metabolite Identification

Common Name

Ellagic acid

Description

Ellagic acid is an organic heterotetracyclic compound resulting from the formal dimerisation of gallic acid by oxidative aromatic coupling with intramolecular lactonisation of both carboxylic acid groups of the resulting biaryl. It is found in many fruits and vegetables, including raspberries, strawberries, cranberries, and pomegranates. It has a role as an antioxidant, a food additive, a plant metabolite, an EC 5.99.1.2 (DNA topoisomerase) inhibitor, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an EC 1.14.18.1 (tyrosinase) inhibitor, an EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor, an EC 2.4.1.1 (glycogen phosphorylase) inhibitor, an EC 2.5.1.18 (glutathione transferase) inhibitor, an EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor, an EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor, an EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor, a skin lightening agent, a fungal metabolite and an EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor. It is an organic heterotetracyclic compound, a cyclic ketone, a lactone, a member of catechols and a polyphenol. It derives from a gallic acid. Ellagic acid, also known as ellagate, belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. The antiproliferative and antioxidant properties of ellagic acid have spurred preliminary research into the potential health benefits of ellagic acid consumption. Ellagic acid's therapeutic action mostly involves antioxidant and anti-proliferative/anti-cancer effects. Ellagic acid is found, on average, in the highest concentration within a few different foods, such as chestnuts, common walnuts, and japanese walnuts and in a lower concentration in whiskies, arctic blackberries, and cloudberries. Ellagic acid has also been detected, but not quantified in several different foods, such as lowbush blueberries, bilberries, guava, strawberry guava, and bog bilberries.

Structure

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

HMDB0002899
     RDKit          3D
Ellagic acid
 28 31  0  0  0  0  0  0  0  0999 V2000
    0.4486    3.0259   -2.0044 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0521    2.0312   -1.3276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2342    1.8225   -1.0988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6835    0.8051   -0.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0405    0.5890   -0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9678    1.4705   -0.6725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4606   -0.4951    0.5721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8210   -0.7263    0.8207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5161   -1.3575    1.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1596   -1.1511    0.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1771   -1.9941    1.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5699   -2.9895    1.9895 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1150   -1.7887    1.0854 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5531   -0.7703    0.3901 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9177   -0.5622    0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8275   -1.4518    0.6704 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3616    0.5148   -0.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6954    0.7836   -0.8490 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3806    1.3837   -1.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0358    1.1910   -0.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6174    0.1037   -0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7364   -0.0651    0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6763    2.2801   -1.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1078   -1.5279    1.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8185   -2.2087    1.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8083   -1.3572    0.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4576    0.2117   -0.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6986    2.2328   -1.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20  2  1  0
 22  4  1  0
 22 10  2  0
 21 14  2  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 16 26  1  0
 18 27  1  0
 19 28  1  0
M  END


  Mrv1652309272007332D          

 22 25  0  0  0  0            999 V2000
10002.5049 9999.8209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.504910001.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.652710002.3032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.515010000.2305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.3641 9997.7467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5150 9998.5752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.365510000.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6510 9999.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6510 9998.9913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3655 9998.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0800 9998.9913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0800 9999.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.652510001.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.938010001.0584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.938010000.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.367010001.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2264 9999.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2264 9998.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9408 9998.5765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.077010001.4725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.791510000.2349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.791510001.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  7 12  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 13 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 21 22  2  0  0  0  0
 22 20  1  0  0  0  0
 22  2  1  0  0  0  0
  1 21  1  0  0  0  0
 18  6  1  0  0  0  0
 17  4  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13  3  2  0  0  0  0
 15 17  2  0  0  0  0
 20 16  2  0  0  0  0
 10  5  2  0  0  0  0
 15  8  1  0  0  0  0
  7 16  1  0  0  0  0
 19  9  1  0  0  0  0
 12 21  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0005328

> <DATABASE_NAME>
MIME

> <SMILES>
OC1=CC2=C3C(OC(=O)C4=CC(O)=C(O)C(OC2=O)=C34)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H6O8/c15-5-1-3-7-8-4(14(20)22-11(7)9(5)17)2-6(16)10(18)12(8)21-13(3)19/h1-2,15-18H

> <INCHI_KEY>
AFSDNFLWKVMVRB-UHFFFAOYSA-N

> <FORMULA>
C14H6O8

> <MOLECULAR_WEIGHT>
302.194

> <EXACT_MASS>
302.006267153

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
26.33823800600257

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,7,13,14-tetrahydroxy-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione

> <ALOGPS_LOGP>
1.59

> <JCHEM_LOGP>
2.315922418

> <ALOGPS_LOGS>
-2.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.223512033465745

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.538315807620176

> <JCHEM_PKA_STRONGEST_BASIC>
-4.79589214812241

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
70.60760000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,7,13,14-tetrahydroxy-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002899
     RDKit          3D
Ellagic acid
 28 31  0  0  0  0  0  0  0  0999 V2000
    0.4486    3.0259   -2.0044 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0521    2.0312   -1.3276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2342    1.8225   -1.0988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6835    0.8051   -0.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0405    0.5890   -0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9678    1.4705   -0.6725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4606   -0.4951    0.5721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8210   -0.7263    0.8207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5161   -1.3575    1.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1596   -1.1511    0.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1771   -1.9941    1.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5699   -2.9895    1.9895 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1150   -1.7887    1.0854 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5531   -0.7703    0.3901 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9177   -0.5622    0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8275   -1.4518    0.6704 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3616    0.5148   -0.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6954    0.7836   -0.8490 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3806    1.3837   -1.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0358    1.1910   -0.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6174    0.1037   -0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7364   -0.0651    0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6763    2.2801   -1.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1078   -1.5279    1.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8185   -2.2087    1.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8083   -1.3572    0.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4576    0.2117   -0.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6986    2.2328   -1.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20  2  1  0
 22  4  1  0
 22 10  2  0
 21 14  2  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 16 26  1  0
 18 27  1  0
 19 28  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    8671.3428666.332   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8671.3428669.420   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8666.0188670.966   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8662.0288667.097   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8667.3468662.461   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8662.0288664.007   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8667.3498667.094   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8666.0158666.324   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8666.0158664.784   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8667.3498664.014   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8668.6838664.784   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8668.6838666.324   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.0188669.412   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8664.6848668.642   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    8664.6848667.102   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8667.3528668.642   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8663.3568666.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8663.3568664.779   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8664.6898664.009   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8668.6778669.415   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8670.0118667.105   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8670.0118668.645   0.000  0.00  0.00           C+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3   13                                                            
CONECT    4   17                                                            
CONECT    5   10                                                            
CONECT    6   18                                                            
CONECT    7    8   12   16                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11    5                                                  
CONECT   11   10   12                                                       
CONECT   12    7   11   21                                                  
CONECT   13   16   14    3                                                  
CONECT   14   13   15                                                       
CONECT   15   14   17    8                                                  
CONECT   16   13   20    7                                                  
CONECT   17   18    4   15                                                  
CONECT   18   17   19    6                                                  
CONECT   19   18    9                                                       
CONECT   20   22   16                                                       
CONECT   21   22    1   12                                                  
CONECT   22   21   20    2                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0002899
HETATM    1  O1  UNL     1       0.449   3.026  -2.004  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.052   2.031  -1.328  1.00  0.00           C  
HETATM    3  O2  UNL     1      -1.234   1.822  -1.099  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.683   0.805  -0.403  1.00  0.00           C  
HETATM    5  C3  UNL     1      -3.040   0.589  -0.165  1.00  0.00           C  
HETATM    6  O3  UNL     1      -3.968   1.471  -0.672  1.00  0.00           O  
HETATM    7  C4  UNL     1      -3.461  -0.495   0.572  1.00  0.00           C  
HETATM    8  O4  UNL     1      -4.821  -0.726   0.821  1.00  0.00           O  
HETATM    9  C5  UNL     1      -2.516  -1.358   1.066  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.160  -1.151   0.834  1.00  0.00           C  
HETATM   11  C7  UNL     1      -0.177  -1.994   1.312  1.00  0.00           C  
HETATM   12  O5  UNL     1      -0.570  -2.990   1.989  1.00  0.00           O  
HETATM   13  O6  UNL     1       1.115  -1.789   1.085  1.00  0.00           O  
HETATM   14  C8  UNL     1       1.553  -0.770   0.390  1.00  0.00           C  
HETATM   15  C9  UNL     1       2.918  -0.562   0.156  1.00  0.00           C  
HETATM   16  O7  UNL     1       3.828  -1.452   0.670  1.00  0.00           O  
HETATM   17  C10 UNL     1       3.362   0.515  -0.578  1.00  0.00           C  
HETATM   18  O8  UNL     1       4.695   0.784  -0.849  1.00  0.00           O  
HETATM   19  C11 UNL     1       2.381   1.384  -1.073  1.00  0.00           C  
HETATM   20  C12 UNL     1       1.036   1.191  -0.851  1.00  0.00           C  
HETATM   21  C13 UNL     1       0.617   0.104  -0.112  1.00  0.00           C  
HETATM   22  C14 UNL     1      -0.736  -0.065   0.096  1.00  0.00           C  
HETATM   23  H1  UNL     1      -3.676   2.280  -1.221  1.00  0.00           H  
HETATM   24  H2  UNL     1      -5.108  -1.528   1.364  1.00  0.00           H  
HETATM   25  H3  UNL     1      -2.818  -2.209   1.643  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.808  -1.357   0.538  1.00  0.00           H  
HETATM   27  H5  UNL     1       5.458   0.212  -0.531  1.00  0.00           H  
HETATM   28  H6  UNL     1       2.699   2.233  -1.650  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   20
CONECT    3    4
CONECT    4    5    5   22
CONECT    5    6    7
CONECT    6   23
CONECT    7    8    9    9
CONECT    8   24
CONECT    9   10   25
CONECT   10   11   22   22
CONECT   11   12   12   13
CONECT   13   14
CONECT   14   15   21   21
CONECT   15   16   17   17
CONECT   16   26
CONECT   17   18   19
CONECT   18   27
CONECT   19   20   20   28
CONECT   20   21
CONECT   21   22
END

HMDB0002899
     RDKit          3D
Ellagic acid
 28 31  0  0  0  0  0  0  0  0999 V2000
    0.4486    3.0259   -2.0044 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0521    2.0312   -1.3276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2342    1.8225   -1.0988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6835    0.8051   -0.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0405    0.5890   -0.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9678    1.4705   -0.6725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4606   -0.4951    0.5721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8210   -0.7263    0.8207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5161   -1.3575    1.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1596   -1.1511    0.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1771   -1.9941    1.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5699   -2.9895    1.9895 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1150   -1.7887    1.0854 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5531   -0.7703    0.3901 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9177   -0.5622    0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8275   -1.4518    0.6704 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3616    0.5148   -0.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6954    0.7836   -0.8490 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3806    1.3837   -1.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0358    1.1910   -0.8509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6174    0.1037   -0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7364   -0.0651    0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6763    2.2801   -1.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1078   -1.5279    1.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8185   -2.2087    1.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8083   -1.3572    0.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4576    0.2117   -0.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6986    2.2328   -1.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20  2  1  0
 22  4  1  0
 22 10  2  0
 21 14  2  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 16 26  1  0
 18 27  1  0
 19 28  1  0
M  END

Synonyms

Value	Source
2,3,7,8-Tetrahydroxy[1]benzopyrano[5,4,3-cde][1]benzopyran-5,10-dione	ChEBI
4,4',5,5',6,6'-Hexahydroxydiphenic acid 2,6,2',6'-dilactone	ChEBI
Acide ellagique	ChEBI
Acido elagico	ChEBI
Acidum ellagicum	ChEBI
Benzoaric acid	ChEBI
Ellagsaeure	ChEBI
Lagistase	ChEBI
4,4',5,5',6,6'-Hexahydroxydiphenate 2,6,2',6'-dilactone	Generator
Benzoarate	Generator
Ellagate	Generator
Acid, benzoaric	MeSH
Acid, ellagic	MeSH
Alizarine yellow	HMDB
Elagostasine	HMDB
Eleagate	HMDB
Eleagic acid	HMDB
Ellagic acid dihydrate	HMDB
Ellagic acid hydrate	HMDB
Gallogen	HMDB
Llagate	HMDB
Llagic acid	HMDB
Ellagic acid	PhytoBank

Molecular Formula

C₁₄H₆O₈

Average Mass

302.194

Monoisotopic Mass

302.006267153

IUPAC Name

6,7,13,14-tetrahydroxy-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione

Traditional Name

6,7,13,14-tetrahydroxy-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione

CAS Registry Number

Not Available

SMILES

OC1=CC2=C3C(OC(=O)C4=CC(O)=C(O)C(OC2=O)=C34)=C1O

InChI Identifier

InChI=1S/C14H6O8/c15-5-1-3-7-8-4(14(20)22-11(7)9(5)17)2-6(16)10(18)12(8)21-13(3)19/h1-2,15-18H

InChI Key

AFSDNFLWKVMVRB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Ellagic_acid
7,8-dihydroxycoumarin
Coumarin
Isocoumarin
Benzopyran
2-benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Polyol
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cyclic ketone (CHEBI:4775 )
organic heterotetracyclic compound (CHEBI:4775 )
catechols (CHEBI:4775 )
polyphenol (CHEBI:4775 )
lactone (CHEBI:4775 )
Ellagitannins (C10788 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.82 g/L	ALOGPS
logP	1.59	ALOGPS
logP	2.32	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	5.54	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.61 m³·mol⁻¹	ChemAxon
Polarizability	26.34 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uk9-0095000000-fbb3052375510a43a32e	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0100-3000090000-98c2eaf6f099a674f556	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-0009000000-40fcade2aa63aa93a2ae	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0zi0-0192000000-778eac8f3ed58bcaac74	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-0zi0-0093000000-8a6cc05fc65249815e82	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0zfr-1589000000-a4f6e3a25012f7426f7d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0a6r-0192000000-39923f8b1dd96716ea79	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001i-0090000000-a1f823c8fd710f0476d9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0039000000-911cfbddb0cc618af274	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0zfr-1589000000-a4f6e3a25012f7426f7d	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-67c5a949d6d186ed40d5	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0039000000-d2f61e8b5cdaa0f142ba	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0090000000-961daa97dff240069d92	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0029000000-246b5797e3aacdc8f2f2	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0059000000-cc29f1c85d471f50bb6b	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-114i-0190000000-6c3c3d5d2c468609b612	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-9600b3c9d9dcbf3cca2a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0029000000-9f6b76087b40406d9ff3	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0090000000-e7359efe114a8fa3c0e3	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-49d4f264ad1b5c5b0fff	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0009000000-49d4f264ad1b5c5b0fff	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6s-0090000000-6cad49e11cb1c2a2c0ee	2021-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)		2012-12-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO, experimental)		2021-10-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO, experimental)		2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Fibroblasts

Tissue Locations

Fibroblasts

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	3	Human feces; Human saliva	Metabolic reconstruction; Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Food		Coffea arabica	FooDB	Phenol Explorer
Food			FooDB	Phenol Explorer
Food			FooDB	Phenol Explorer
Food		Coffea canephora	FooDB	Phenol Explorer
Food			FooDB	Phenol Explorer
Plant	Flower	Punica granatum	FooDB	DUKE
Plant		Syzygium cumini	FooDB	24285751
Plant	Plant	Vaccinium corymbosum	FooDB	DUKE
Plant	Fruit	Vaccinium corymbosum	FooDB	S.Hakkinen, M. Heinonen, S. Karenlampi, H. Mykkanen, J. Ruuskanen, R. Torronen. Screening of selected flavonoids and phenolic acids in 19 berries. Food Research International 32 (1999) 345-353. https://www.sciencedirect.com/science/article/pii/S0963996999000952
Plant	Fruit	Rubus idaeus	FooDB	Phenol Explorer
Plant	Fruit	Rubus idaeus	FooDB	Phenol Explorer
Plant	Fruit	Juglans regia	FooDB	DUKE
Plant		Rubus	FooDB	PhytoHub
Plant	Fruit	Rubus idaeus	FooDB	S.Hakkinen, M. Heinonen, S. Karenlampi, H. Mykkanen, J. Ruuskanen, R. Torronen. Screening of selected flavonoids and phenolic acids in 19 berries. Food Research International 32 (1999) 345-353. https://www.sciencedirect.com/science/article/pii/S0963996999000952
Plant		Fragaria x ananassa	FooDB	PhytoHub
Plant	Fruit	Rubus idaeus	FooDB	Phenol Explorer
Plant	Fruit	Rubus idaeus	FooDB	24285751
Plant		Juglans ailanthifolia	FooDB	Phenol Explorer
Plant		Juglans ailanthifolia	FooDB	Phenol Explorer
Plant	Fruit	Vaccinium corymbosum	FooDB	Phenol Explorer
Plant	Fruit	Rubus arcticus	FooDB	Phenol Explorer
Plant	Fruit	Vaccinium macrocarpon	FooDB	S.Hakkinen, M. Heinonen, S. Karenlampi, H. Mykkanen, J. Ruuskanen, R. Torronen. Screening of selected flavonoids and phenolic acids in 19 berries. Food Research International 32 (1999) 345-353. https://www.sciencedirect.com/science/article/pii/S0963996999000952
Plant	Juice	Punica granatum	FooDB	Phenol Explorer
Plant	Seed	Juglans regia	FooDB	DUKE
Plant	Juice	Punica granatum	FooDB	Phenol Explorer
Plant		Rubus idaeus	FooDB	PhytoHub
Plant	Fruit	Juglans nigra	FooDB	DUKE
Plant	Fruit	Vaccinium angustifolium	FooDB	Phenol Explorer
Plant	Testa	Juglans regia	FooDB	DUKE
Plant	Root	Daucus carota ssp. sativus	FooDB	Phenol Explorer
Plant	Fruit	Vaccinium corymbosum	FooDB	Phenol Explorer
Plant	Fruit	Vaccinium corymbosum	FooDB	Sellappan S, Akoh CC, Krewer G. Phenolic Compounds and Antioxidant Capacity of Georgia-Grown Blueberries and Blackberries. 2002. J. Agric. Food Chem. 2002, 50, 2432-2438
Plant	Fruit	Malus pumila	FooDB	Phenol Explorer
Plant	Juice	Vitis rotundifolia	FooDB	Phenol Explorer
Plant	Juice	Vitis rotundifolia	FooDB	Phenol Explorer
Plant		Vitis	FooDB	PhytoHub
Plant		Prunus persica	FooDB	PhytoHub
Plant	Seed	Trigonella foenum-graecum	FooDB	Phenol Explorer
Plant	Plant	Psidium cattleianum	FooDB	DUKE
Plant		Trigonella foenum-graecum	FooDB	Phenol Explorer
Plant		Juglans regia	FooDB	Phenol Explorer
Plant		Juglans regia	FooDB	Phenol Explorer
Plant		Vaccinium macrocarpon	FooDB	PhytoHub
Plant	Nut	Juglans regia	FooDB	Phenol Explorer
Plant	Shoot	Juglans nigra	FooDB	DUKE
Plant		Juglans regia	FooDB	PhytoHub
Plant		Punica granatum	FooDB	24285751
Plant	Fruit	Vitis vinifera	FooDB	DUKE
Plant	Fruit	Rubus	FooDB	Sellappan S, Akoh CC, Krewer G. Phenolic Compounds and Antioxidant Capacity of Georgia-Grown Blueberries and Blackberries. 2002. J. Agric. Food Chem. 2002, 50, 2432-2438
Plant		Punica granatum	FooDB	PhytoHub
Plant		Coriandrum sativum	FooDB	Phenol Explorer
Plant	Fruit	Rubus	FooDB	17896814
Plant	Fruit	Rubus chamaemorus	FooDB	Phenol Explorer
Plant	Fruit	Rubus chamaemorus	FooDB	Phenol Explorer
Plant	Fruit	Fragaria x ananassa	FooDB	Phenol Explorer
Plant	Fruit	Fragaria x ananassa	FooDB	Phenol Explorer
Plant		Carya illinoinensis	FooDB	PhytoHub
Plant	Bark	Psidium guajava	FooDB	DUKE
Plant	Fruit	Vaccinium virgatum	FooDB	Sellappan S, Akoh CC, Krewer G. Phenolic Compounds and Antioxidant Capacity of Georgia-Grown Blueberries and Blackberries. 2002. J. Agric. Food Chem. 2002, 50, 2432-2438
Plant	Fruit	Fragaria x ananassa	FooDB	S.Hakkinen, M. Heinonen, S. Karenlampi, H. Mykkanen, J. Ruuskanen, R. Torronen. Screening of selected flavonoids and phenolic acids in 19 berries. Food Research International 32 (1999) 345-353. https://www.sciencedirect.com/science/article/pii/S0963996999000952
Plant	Fruit	Vaccinium myrtillus	FooDB	Phenol Explorer
Plant	Bark	Syzygium aromaticum	FooDB	DUKE
Plant	Top part	Brassica rapa var. rapa	FooDB	Phenol Explorer
Plant	Fruit	Solanum lycopersicum var. lycopersicum	FooDB	Phenol Explorer
Plant	Bark	Bertholletia excelsa	FooDB	DUKE
Plant	Fruit	Rubus occidentalis	FooDB	Phenol Explorer
Plant	Leaves	Oenothera biennis	FooDB	DUKE
Plant		Vaccinium oxycoccos	FooDB	PhytoHub
Plant	Fruit	Vitis vinifera	FooDB	Phenol Explorer
Plant	Fruit	Vaccinium uliginosum	FooDB	Phenol Explorer
Plant	Fruit	Vitis vinifera	FooDB	Phenol Explorer
Plant	Nut	Castanea	FooDB	Phenol Explorer
Plant	Leaves	Castanea sativa	FooDB	DUKE
Plant	Juice	Rubus idaeus	FooDB	DUKE
Plant	Plant	Salvia officinalis	FooDB	DUKE

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

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	0.067	0.0056			uM	Adult (>18 years old)	Both	Normal	HMDB	15369737
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0002899

DrugBank ID

DB08846

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ellagic_acid

METLIN ID

3430

PubChem Compound

5281855

PDB ID

Not Available

ChEBI ID

4775

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Glover D, Warner ED: The CLUE test. A multiparameter coagulation and fibrinolysis screening test using the platelet aggregometer. Am J Clin Pathol. 1975 Jan;63(1):74-80. doi: 10.1093/ajcp/63.3.74. [PubMed:1111277 ]
Kaiser B, Fareed J, Hoppensteadt D, Birdsong B, Walenga JM, Markwardt F: Influence of recombinant hirudin and unfractionated heparin on thrombin and factor Xa generation in extrinsic and intrinsic activated systems. Thromb Res. 1992 Jan 15;65(2):157-64. doi: 10.1016/0049-3848(92)90235-3. [PubMed:1579892 ]
Banzouzi JT, Prado R, Menan H, Valentin A, Roumestan C, Mallie M, Pelissier Y, Blache Y: In vitro antiplasmodial activity of extracts of Alchornea cordifolia and identification of an active constituent: ellagic acid. J Ethnopharmacol. 2002 Aug;81(3):399-401. doi: 10.1016/s0378-8741(02)00121-6. [PubMed:12127243 ]
Cerda B, Espin JC, Parra S, Martinez P, Tomas-Barberan FA: The potent in vitro antioxidant ellagitannins from pomegranate juice are metabolised into bioavailable but poor antioxidant hydroxy-6H-dibenzopyran-6-one derivatives by the colonic microflora of healthy humans. Eur J Nutr. 2004 Aug;43(4):205-20. doi: 10.1007/s00394-004-0461-7. Epub 2004 Jan 6. [PubMed:15309440 ]
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Showing metabocard for Ellagic acid (MMDBc0005328)

MOL for #<Metabolite:0x00007fdb21eb72e8>

3D MOL for #<Metabolite:0x00007fdb21eb72e8>

3D SDF for #<Metabolite:0x00007fdb21eb72e8>

3D-SDF for #<Metabolite:0x00007fdb21eb72e8>

PDB for #<Metabolite:0x00007fdb21eb72e8>

3D PDB for #<Metabolite:0x00007fdb21eb72e8>

SMILES for #<Metabolite:0x00007fdb21eb72e8>

INCHI for #<Metabolite:0x00007fdb21eb72e8>

Structure for #<Metabolite:0x00007fdb21eb72e8>

3D Structure for #<Metabolite:0x00007fdb21eb72e8>