Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:18 UTC

Update Date

2022-03-07 02:49:17 UTC

HMDB ID

HMDB0002899

Secondary Accession Numbers

HMDB02899

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>
HMDB0002899

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View Stereo Labels

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

Chemical Formula

C₁₄H₆O₈

Average Molecular Weight

302.194

Monoisotopic Molecular Weight

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

476-66-4

SMILES

OC1=C(O)C2=C3C(=C1)C(=O)OC1=C3C(=CC(O)=C1O)C(=O)O2

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 )

Ontology

Not Available

Fibroblasts (HMDB: HMDB0002899)

Fibroblast

Fibroblast (HMDB: HMDB0002899)

Biofluid or Excreta

Non-excretory biofluid

Blood (PMID: 15369737)

Excreta

Urine (PMID: 16172180)

Blood (HMDB: HMDB0002899)
Urine (HMDB: HMDB0002899)

Cellular substructure

Membrane (HMDB: HMDB0002899)

Membrane (HMDB: HMDB0002899)
Cell membrane (HMDB: HMDB0002899)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002899)

Source

Exogenous

Food

Food (HMDB: HMDB0002899)

Fruit

Pome

Apple (FooDB: FOOD00105)

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Grape (FooDB: FOOD00369)
Strawberry (FooDB: FOOD00083)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Lowbush blueberry (FooDB: FOOD00189)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bog bilberry (FooDB: FOOD00212)
European cranberry (FooDB: FOOD00217)
Evergreen blackberry (FooDB: FOOD00901)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Tropical highland blackberry (FooDB: FOOD00904)

Tropical fruit

Drupe

Peach (FooDB: FOOD00149)

Beverage

Distilled beverage

Spirit (FooDB: FOOD00276)
Liquor (FooDB: FOOD00616)
Rum (FooDB: FOOD00629)
Whisky (FooDB: FOOD00623)

Other beverage

Fruit juice (FooDB: FOOD00763)

Fermented beverage

Grape wine (FooDB: FOOD00612)

Nut

Vegetable

Root vegetable

Carrot (FooDB: FOOD00245)

Fruit vegetable

Garden tomato (var.) (FooDB: FOOD00173)

Coffee and coffee product

Cloves (FooDB: FOOD00179)

Oilseed crop

Evening primrose (FooDB: FOOD00120)

Cereal and cereal product

Leavened bread

Rye bread (FooDB: FOOD00809)

Not Available

Industrial application

Manufacturing industry

Material processing agent

pesticide (HMDB: HMDB0002899)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0002899)

EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (HMDB: HMDB0002899)
angiotensin converting enzyme inhibitor (HMDB: HMDB0002899)
EC 1.1.1.21 (aldehyde reductase) inhibitor (HMDB: HMDB0002899)
Candida-secreted-aspartyl-proteinase inhibitor (HMDB: HMDB0002899)
deiodinase inhibitor (HMDB: HMDB0002899)
glucosyl-transferase inhibitor (HMDB: HMDB0002899)
HIV-reverse-transcriptase inhibitor (HMDB: HMDB0002899)
EC 1.17.3.2 (xanthine oxidase) inhibitor (HMDB: HMDB0002899)

anti aflatoxin (HMDB: HMDB0002899)
anti anaphylactic (HMDB: HMDB0002899)
anti bacterial (HMDB: HMDB0002899)
anti cancer (HMDB: HMDB0002899)
anti cariogenic (HMDB: HMDB0002899)
anti cataract (HMDB: HMDB0002899)
anti gingivitic (HMDB: HMDB0002899)
anti glucose-tolerance-factor (HMDB: HMDB0002899)
anti HIV (HMDB: HMDB0002899)
anti hyperthyroid (HMDB: HMDB0002899)
anti inflammatory (HMDB: HMDB0002899)
anti malarial (HMDB: HMDB0002899)
anti mutagenic (HMDB: HMDB0002899)
Antioxidant (HMDB: HMDB0002899)
anti periodontic (HMDB: HMDB0002899)
anti peroxidant (HMDB: HMDB0002899)
anti plaque (HMDB: HMDB0002899)
anti plasmodial (HMDB: HMDB0002899)
anti septic (HMDB: HMDB0002899)
anti streptococcic (HMDB: HMDB0002899)
anti thyroid (HMDB: HMDB0002899)
antitumor (HMDB: HMDB0002899)
antiviral agent (HMDB: HMDB0002899)
anti yeast (HMDB: HMDB0002899)
apoptotic (HMDB: HMDB0002899)
cancer preventive (HMDB: HMDB0002899)
cytotoxic (HMDB: HMDB0002899)
detoxicant (HMDB: HMDB0002899)
hemostatic (HMDB: HMDB0002899)
hepatoprotective (HMDB: HMDB0002899)
juvabional (HMDB: HMDB0002899)
quinone-reductase inducer (HMDB: HMDB0002899)
sunscreen (HMDB: HMDB0002899)
topoisomerase-I antagonist (HMDB: HMDB0002899)

Indirect biological role

antioxidant (HMDB: HMDB0002899)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	> 360 °C	Not Available
Boiling Point	796.50 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	78280 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.239 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	165.494	31661259
DarkChem	[M-H]-	164.651	31661259
DeepCCS	[M+H]+	165.706	30932474
DeepCCS	[M-H]-	163.348	30932474
DeepCCS	[M-2H]-	197.315	30932474
DeepCCS	[M+Na]+	172.672	30932474
AllCCS	[M+H]+	164.0	32859911
AllCCS	[M+H-H2O]+	160.4	32859911
AllCCS	[M+NH4]+	167.3	32859911
AllCCS	[M+Na]+	168.3	32859911
AllCCS	[M-H]-	163.9	32859911
AllCCS	[M+Na-2H]-	162.8	32859911
AllCCS	[M+HCOO]-	161.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ellagic acid	OC1=C(O)C2=C3C(=C1)C(=O)OC1=C3C(=CC(O)=C1O)C(=O)O2	4350.7	Standard polar	33892256
Ellagic acid	OC1=C(O)C2=C3C(=C1)C(=O)OC1=C3C(=CC(O)=C1O)C(=O)O2	2157.1	Standard non polar	33892256
Ellagic acid	OC1=C(O)C2=C3C(=C1)C(=O)OC1=C3C(=CC(O)=C1O)C(=O)O2	3096.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ellagic acid,1TMS,isomer #1	C[Si](C)(C)OC1=CC2=C3C(=C1O)OC(=O)C1=CC(O)=C(O)C(=C13)OC2=O	3339.3	Semi standard non polar	33892256
Ellagic acid,1TMS,isomer #2	C[Si](C)(C)OC1=C(O)C=C2C(=O)OC3=C4C(=CC(O)=C3O)C(=O)OC1=C24	3292.6	Semi standard non polar	33892256
Ellagic acid,2TMS,isomer #1	C[Si](C)(C)OC1=CC2=C3C(=C1O)OC(=O)C1=CC(O)=C(O[Si](C)(C)C)C(=C13)OC2=O	3375.8	Semi standard non polar	33892256
Ellagic acid,2TMS,isomer #2	C[Si](C)(C)OC1=CC2=C3C(=C1O)OC(=O)C1=CC(O[Si](C)(C)C)=C(O)C(=C13)OC2=O	3437.3	Semi standard non polar	33892256
Ellagic acid,2TMS,isomer #3	C[Si](C)(C)OC1=CC2=C3C(=C1O[Si](C)(C)C)OC(=O)C1=CC(O)=C(O)C(=C13)OC2=O	3264.9	Semi standard non polar	33892256
Ellagic acid,2TMS,isomer #4	C[Si](C)(C)OC1=C(O)C=C2C(=O)OC3=C4C(=CC(O)=C3O[Si](C)(C)C)C(=O)OC1=C24	3310.1	Semi standard non polar	33892256
Ellagic acid,3TMS,isomer #1	C[Si](C)(C)OC1=CC2=C3C(=C1O)OC(=O)C1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(=C13)OC2=O	3308.2	Semi standard non polar	33892256
Ellagic acid,3TMS,isomer #2	C[Si](C)(C)OC1=CC2=C3C(=C1O[Si](C)(C)C)OC(=O)C1=CC(O)=C(O[Si](C)(C)C)C(=C13)OC2=O	3265.6	Semi standard non polar	33892256
Ellagic acid,4TMS,isomer #1	C[Si](C)(C)OC1=CC2=C3C(=C1O[Si](C)(C)C)OC(=O)C1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(=C13)OC2=O	3201.2	Semi standard non polar	33892256
Ellagic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C3C(=C1O)OC(=O)C1=CC(O)=C(O)C(=C13)OC2=O	3562.6	Semi standard non polar	33892256
Ellagic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(O)C=C2C(=O)OC3=C4C(=CC(O)=C3O)C(=O)OC1=C24	3527.0	Semi standard non polar	33892256
Ellagic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C3C(=C1O)OC(=O)C1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(=C13)OC2=O	3862.6	Semi standard non polar	33892256
Ellagic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C3C(=C1O)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C(O)C(=C13)OC2=O	3899.9	Semi standard non polar	33892256
Ellagic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC2=C3C(=C1O[Si](C)(C)C(C)(C)C)OC(=O)C1=CC(O)=C(O)C(=C13)OC2=O	3729.2	Semi standard non polar	33892256
Ellagic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=C(O)C=C2C(=O)OC3=C4C(=CC(O)=C3O[Si](C)(C)C(C)(C)C)C(=O)OC1=C24	3816.0	Semi standard non polar	33892256
Ellagic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C3C(=C1O)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(=C13)OC2=O	3996.6	Semi standard non polar	33892256
Ellagic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C3C(=C1O[Si](C)(C)C(C)(C)C)OC(=O)C1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(=C13)OC2=O	3950.5	Semi standard non polar	33892256
Ellagic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C3C(=C1O[Si](C)(C)C(C)(C)C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(=C13)OC2=O	4019.2	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 - Ellagic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uk9-0095000000-fbb3052375510a43a32e	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ellagic acid GC-MS (4 TMS) - 70eV, Positive	splash10-0100-3000090000-98c2eaf6f099a674f556	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ellagic acid 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 - Ellagic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0udi-0009000000-40fcade2aa63aa93a2ae	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ellagic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0zi0-0192000000-778eac8f3ed58bcaac74	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ellagic acid DI-ESI-qTof , Positive-QTOF	splash10-0zi0-0093000000-8a6cc05fc65249815e82	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ellagic acid LC-ESI-qTof , Positive-QTOF	splash10-0zfr-1589000000-a4f6e3a25012f7426f7d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ellagic acid Linear Ion Trap , negative-QTOF	splash10-0a6r-0192000000-39923f8b1dd96716ea79	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ellagic acid Linear Ion Trap , positive-QTOF	splash10-001i-0090000000-a1f823c8fd710f0476d9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ellagic acid Linear Ion Trap , positive-QTOF	splash10-0udi-0039000000-911cfbddb0cc618af274	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ellagic acid , positive-QTOF	splash10-0zfr-1589000000-a4f6e3a25012f7426f7d	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ellagic acid 10V, Positive-QTOF	splash10-0udi-0009000000-67c5a949d6d186ed40d5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ellagic acid 20V, Positive-QTOF	splash10-0udi-0039000000-d2f61e8b5cdaa0f142ba	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ellagic acid 40V, Positive-QTOF	splash10-000i-0090000000-961daa97dff240069d92	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ellagic acid 10V, Negative-QTOF	splash10-0udi-0029000000-246b5797e3aacdc8f2f2	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ellagic acid 20V, Negative-QTOF	splash10-0udi-0059000000-cc29f1c85d471f50bb6b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ellagic acid 40V, Negative-QTOF	splash10-114i-0190000000-6c3c3d5d2c468609b612	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ellagic acid 10V, Negative-QTOF	splash10-0udi-0009000000-9600b3c9d9dcbf3cca2a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ellagic acid 20V, Negative-QTOF	splash10-0udi-0029000000-9f6b76087b40406d9ff3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ellagic acid 40V, Negative-QTOF	splash10-0006-0090000000-e7359efe114a8fa3c0e3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ellagic acid 10V, Positive-QTOF	splash10-0udi-0009000000-49d4f264ad1b5c5b0fff	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ellagic acid 20V, Positive-QTOF	splash10-0udi-0009000000-49d4f264ad1b5c5b0fff	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ellagic acid 40V, Positive-QTOF	splash10-0a6s-0090000000-6cad49e11cb1c2a2c0ee	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Fibroblasts

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 417	16172180	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 417	20218618	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 417	16988113	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 417	18598186	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 417	17090147	details
Blood	Detected and Quantified	0.067 +/- 0.0056 uM	Adult (>18 years old)	Both	Normal	15369737	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 417	16172180	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 417	20218618	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 417	16988113	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 417	18598186	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 417	17090147	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

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

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1098851

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Stoner GD, Sardo C, Apseloff G, Mullet D, Wargo W, Pound V, Singh A, Sanders J, Aziz R, Casto B, Sun X: Pharmacokinetics of anthocyanins and ellagic acid in healthy volunteers fed freeze-dried black raspberries daily for 7 days. J Clin Pharmacol. 2005 Oct;45(10):1153-64. [PubMed:16172180 ]
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. [PubMed:1111277 ]
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. [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. Epub 2004 Jan 6. [PubMed:15309440 ]
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. [PubMed:1579892 ]
Jimenez F, Mitts TF, Liu K, Wang Y, Hinek A: Ellagic and tannic acids protect newly synthesized elastic fibers from premature enzymatic degradation in dermal fibroblast cultures. J Invest Dermatol. 2006 Jun;126(6):1272-80. [PubMed:16601672 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Ellagic acid → 3,4,5-trihydroxy-6-({6,13,14-trihydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaen-7-yl}oxy)oxane-2-carboxylic acid	details
Ellagic acid → 3,4,5-trihydroxy-6-({7,13,14-trihydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(15),4,6,8(16),11,13-hexaen-6-yl}oxy)oxane-2-carboxylic acid	details

Showing metabocard for Ellagic acid (HMDB0002899)

MOL for HMDB0002899 (Ellagic acid)

3D MOL for HMDB0002899 (Ellagic acid)

3D SDF for HMDB0002899 (Ellagic acid)

3D-SDF for HMDB0002899 (Ellagic acid)

PDB for HMDB0002899 (Ellagic acid)

3D PDB for HMDB0002899 (Ellagic acid)

SMILES for HMDB0002899 (Ellagic acid)

INCHI for HMDB0002899 (Ellagic acid)

Structure for HMDB0002899 (Ellagic acid)

3D Structure for HMDB0002899 (Ellagic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions