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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

2021-09-07 16:45:34 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 SDF 3D SDF PDB 3D PDB SMILES InChI


  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

$$$$

https://cactus.nci.nih.gov/chemical/structure/OC1=C(O)C2=C3C(=C1)C(=O)OC1=C3C...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:27})
 28 31  0  0  0  0  0  0  0  0999 V2000
    4.7691   -0.8037    0.0148 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4281   -0.5796    0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9597    0.7314    0.1283 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8414    1.7635    0.1905 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917    0.9841    0.1593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7267   -0.1040    0.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1921   -1.4320   -0.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5616   -1.6601   -0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1690   -2.4814   -0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4470   -3.5554   -0.6586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0862   -2.2374    0.2861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5909   -0.9841    0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7263    0.1037    0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1922    1.4321   -0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5616    1.6611   -0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4278    0.5807    0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7688    0.8050    0.0521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9591   -0.7302    0.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8406   -1.7613    0.2333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1697    2.4826   -0.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4482    3.5592   -0.6396 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0864    2.2350    0.2967 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1582   -0.9322    0.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0875    2.1231   -0.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9476   -2.6666   -0.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9478    2.6675   -0.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1622    0.8041   -0.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0979   -2.1244   -0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 23  1  0  0  0  0
  2  3  2  0  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4 24  1  0  0  0  0
  5  6  2  0  0  0  0
  5 22  1  0  0  0  0
  6  7  1  0  0  0  0
  6 13  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  8 25  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 18  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 20  1  0  0  0  0
 15 16  1  0  0  0  0
 15 26  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 17 27  1  0  0  0  0
 18 19  1  0  0  0  0
 19 28  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  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    https://cactus.nci.nih.gov/chemical/structure/OC1=C(O)C2=C3C(=C1)C(=O)OC1=C3C... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  O   UNL     1       4.769  -0.804   0.015  1.00  0.00           O  
HETATM    2  C   UNL     1       3.428  -0.580   0.033  1.00  0.00           C  
HETATM    3  C   UNL     1       2.960   0.731   0.128  1.00  0.00           C  
HETATM    4  O   UNL     1       3.841   1.764   0.191  1.00  0.00           O  
HETATM    5  C   UNL     1       1.592   0.984   0.159  1.00  0.00           C  
HETATM    6  C   UNL     1       0.727  -0.104   0.075  1.00  0.00           C  
HETATM    7  C   UNL     1       1.192  -1.432  -0.035  1.00  0.00           C  
HETATM    8  C   UNL     1       2.562  -1.660  -0.050  1.00  0.00           C  
HETATM    9  C   UNL     1       0.169  -2.481  -0.160  1.00  0.00           C  
HETATM   10  O   UNL     1       0.447  -3.555  -0.659  1.00  0.00           O  
HETATM   11  O   UNL     1      -1.086  -2.237   0.286  1.00  0.00           O  
HETATM   12  C   UNL     1      -1.591  -0.984   0.171  1.00  0.00           C  
HETATM   13  C   UNL     1      -0.726   0.104   0.079  1.00  0.00           C  
HETATM   14  C   UNL     1      -1.192   1.432  -0.025  1.00  0.00           C  
HETATM   15  C   UNL     1      -2.562   1.661  -0.025  1.00  0.00           C  
HETATM   16  C   UNL     1      -3.428   0.581   0.061  1.00  0.00           C  
HETATM   17  O   UNL     1      -4.769   0.805   0.052  1.00  0.00           O  
HETATM   18  C   UNL     1      -2.959  -0.730   0.156  1.00  0.00           C  
HETATM   19  O   UNL     1      -3.841  -1.761   0.233  1.00  0.00           O  
HETATM   20  C   UNL     1      -0.170   2.483  -0.147  1.00  0.00           C  
HETATM   21  O   UNL     1      -0.448   3.559  -0.640  1.00  0.00           O  
HETATM   22  O   UNL     1       1.086   2.235   0.297  1.00  0.00           O  
HETATM   23  H   UNL     1       5.158  -0.932   0.891  1.00  0.00           H  
HETATM   24  H   UNL     1       4.088   2.123  -0.673  1.00  0.00           H  
HETATM   25  H   UNL     1       2.948  -2.667  -0.116  1.00  0.00           H  
HETATM   26  H   UNL     1      -2.948   2.667  -0.092  1.00  0.00           H  
HETATM   27  H   UNL     1      -5.162   0.804  -0.831  1.00  0.00           H  
HETATM   28  H   UNL     1      -4.098  -2.124  -0.625  1.00  0.00           H  
CONECT    1    2   23                                                 
CONECT    2    1    3    3    8                                       
CONECT    3    2    2    4    5                                       
CONECT    4    3   24                                                 
CONECT    5    3    6    6   22                                       
CONECT    6    5    5    7   13                                       
CONECT    7    6    8    8    9                                       
CONECT    8    7    7    2   25                                       
CONECT    9    7   10   10   11                                       
CONECT   10    9    9                                                 
CONECT   11    9   12                                                 
CONECT   12   11   13   13   18                                       
CONECT   13   12   12    6   14                                       
CONECT   14   13   15   15   20                                       
CONECT   15   14   14   16   26                                       
CONECT   16   15   17   18   18                                       
CONECT   17   16   27                                                 
CONECT   18   16   16   12   19                                       
CONECT   19   18   28                                                 
CONECT   20   14   21   21   22                                       
CONECT   21   20   20                                                 
CONECT   22   20    5                                                 
CONECT   23    1                                                      
CONECT   24    4                                                      
CONECT   25    8                                                      
CONECT   26   15                                                      
CONECT   27   17                                                      
CONECT   28   19                                                      
MASTER        0    0    0    0    0    0    0    0   28    0   28    0
END

https://cactus.nci.nih.gov/chemical/structure/OC1=C(O)C2=C3C(=C1)C(=O)OC1=C3C...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:27})
 28 31  0  0  0  0  0  0  0  0999 V2000
    4.7691   -0.8037    0.0148 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4281   -0.5796    0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9597    0.7314    0.1283 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8414    1.7635    0.1905 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917    0.9841    0.1593 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7267   -0.1040    0.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1921   -1.4320   -0.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5616   -1.6601   -0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1690   -2.4814   -0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4470   -3.5554   -0.6586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0862   -2.2374    0.2861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5909   -0.9841    0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7263    0.1037    0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1922    1.4321   -0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5616    1.6611   -0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4278    0.5807    0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7688    0.8050    0.0521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9591   -0.7302    0.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8406   -1.7613    0.2333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1697    2.4826   -0.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4482    3.5592   -0.6396 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0864    2.2350    0.2967 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1582   -0.9322    0.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0875    2.1231   -0.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9476   -2.6666   -0.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9478    2.6675   -0.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1622    0.8041   -0.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0979   -2.1244   -0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 23  1  0  0  0  0
  2  3  2  0  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4 24  1  0  0  0  0
  5  6  2  0  0  0  0
  5 22  1  0  0  0  0
  6  7  1  0  0  0  0
  6 13  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  8 25  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 18  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 20  1  0  0  0  0
 15 16  1  0  0  0  0
 15 26  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 17 27  1  0  0  0  0
 18 19  1  0  0  0  0
 19 28  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  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
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
Acid, benzoaric	HMDB
Acid, ellagic	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

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Fibroblast

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	> 360 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	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 Spectral Properties

Collision Cross Sections

Name	Adduct	Type	Data Source	Value	Reference
DarkChem	[M+H]+	Predicted	Not Available	165.494	31661259
DarkChem	[M-H]-	Predicted	Not Available	164.651	31661259

Retention Indices

Underivatized

Not Available

Derivatized

Derivative	Value	Reference
Ellagic acid,1TMS,#1	3339.2876	https://arxiv.org/abs/1905.12712
Ellagic acid,1TMS,#2	3292.6292	https://arxiv.org/abs/1905.12712
Ellagic acid,2TMS,#1	3375.795	https://arxiv.org/abs/1905.12712
Ellagic acid,2TMS,#2	3437.3003	https://arxiv.org/abs/1905.12712
Ellagic acid,2TMS,#3	3264.8691	https://arxiv.org/abs/1905.12712
Ellagic acid,2TMS,#4	3310.0596	https://arxiv.org/abs/1905.12712
Ellagic acid,3TMS,#1	3308.2036	https://arxiv.org/abs/1905.12712
Ellagic acid,3TMS,#2	3265.5989	https://arxiv.org/abs/1905.12712
Ellagic acid,4TMS,#1	3201.2158	https://arxiv.org/abs/1905.12712
Ellagic acid,1TBDMS,#1	3562.5596	https://arxiv.org/abs/1905.12712
Ellagic acid,1TBDMS,#2	3527.0256	https://arxiv.org/abs/1905.12712
Ellagic acid,2TBDMS,#1	3862.566	https://arxiv.org/abs/1905.12712
Ellagic acid,2TBDMS,#2	3899.9182	https://arxiv.org/abs/1905.12712
Ellagic acid,2TBDMS,#3	3729.171	https://arxiv.org/abs/1905.12712
Ellagic acid,2TBDMS,#4	3815.9868	https://arxiv.org/abs/1905.12712
Ellagic acid,3TBDMS,#1	3996.5854	https://arxiv.org/abs/1905.12712
Ellagic acid,3TBDMS,#2	3950.543	https://arxiv.org/abs/1905.12712
Ellagic acid,4TBDMS,#1	4019.1826	https://arxiv.org/abs/1905.12712

Spectra

GC-MS

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

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
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 - 20V, Positive	splash10-0udi-0009000000-49d4f264ad1b5c5b0fff	2021-09-09	View Spectrum

NMR

Spectrum Type	Description	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	2012-12-05	View Spectrum
2D NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, 100%_DMSO, predicted)	2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Fibroblasts

Pathways

Not Available

Name	SMPDB/Pathwhiz	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

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

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. [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 ]
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 ]

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)

Collision Cross Sections

Retention Indices

Underivatized

Derivatized

GC-MS

LC-MS/MS

NMR

Enzymes

Reactions