NP-MRD: Showing NP-Card for epigallocatechin-3-O-gallate (NP0031143)

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Record Information

Version

2.0

Created at

2021-06-19 22:18:31 UTC

Updated at

2021-08-20 00:00:23 UTC

NP-MRD ID

NP0031143

Secondary Accession Numbers

None

Natural Product Identification

Common Name

epigallocatechin-3-O-gallate

Provided By

JEOL Database JEOL Logo

Description

Epigallocatechin gallate, also known as EGCG or catechin deriv., Belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin. Epigallocatechin gallate has been detected, but not quantified in, black tea and green tea. This could make epigallocatechin gallate a potential biomarker for the consumption of these foods. Epigallocatechin gallate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. epigallocatechin-3-O-gallate is found in Senegalia polyacantha, Alhagi sparsifolia, Alnus sieboldiana, Averrhoa carambola L., Camellia crassicolumna, Camellia taliensis, Coccoloba mollis, Cucurbita pepo, Diospyros kaki, Eschweilera coriacea, Eugenia myrcianthes, Eugenia selloi, Euphorbia hirta, Fagopyrum megacarpum, Hibiscus cannabinus, Hippophae rhamnoides, Limoniastrum guyonianum, Limonium gmelinii, Limonium sinense, Lotus corniculatus, Matricaria chamomilla, Myrica esculenta, Myrica rubra, Morus alba, Myrtus communis, Parapiptadenia rigida, Parkia biglobosa, Phyllanthus niruri, Platycarya strobilacea, Polygonum panjutinii, Dasiphora fruticosa, Prunus dulcis, Pteroxygonum giraldii, Quercus robur, Rhodiola crenulata, Rhodiola heterodonta, Rhodiola kirilowii, Rhodiola sacra, Rhodiola semenovii, Rhododendron ponticum, Rosa rugosa, Sclerocarya birrea, Sedum crassularia, Sempervivum tectorum, Sideroxylon inerme, Terminalia catappa, Theobroma cacao, Trifolium pratense, Turnera ulmifolia, Uncaria guianensis, Vitellaria paradoxa, Vitis vinifera and Ziziphus jujuba. epigallocatechin-3-O-gallate was first documented in 1992 (PMID: 1731169). Based on a literature review a small amount of articles have been published on Epigallocatechin gallate (PMID: 16772446) (PMID: 12832052) (PMID: 16054165) (PMID: 16403950).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100183D          

 51 54  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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  Mrv1652306202100183D          

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   -5.4151   -0.9449    2.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6639   -1.0589    4.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8895   -1.3956    6.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4233   -1.5852    4.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1141   -3.0783    0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5467   -3.7347   -0.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9208   -3.5733   -1.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0241   -1.0672   -0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2397    0.6548    1.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1603   -0.2239    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7707    2.0219    1.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1067    5.2652    1.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4150    6.6884   -1.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1148    5.2519   -3.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5883    3.1105   -2.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 24  2  0  0  0  0
 24 16  1  0  0  0  0
 12 13  2  0  0  0  0
 10 11  1  0  0  0  0
 13 14  1  0  0  0  0
  7  8  1  0  0  0  0
  6  5  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
 20 21  1  0  0  0  0
  4 15  1  0  0  0  0
 18 19  1  0  0  0  0
 15 14  1  0  0  0  0
  3  2  1  0  0  0  0
 13  6  1  0  0  0  0
  2  1  2  0  0  0  0
 15 16  1  0  0  0  0
  2 25  1  0  0  0  0
  7  9  1  0  0  0  0
 25 33  2  0  0  0  0
 16 17  2  0  0  0  0
 33 31  1  0  0  0  0
  6  7  2  0  0  0  0
 31 29  2  0  0  0  0
 17 18  1  0  0  0  0
 29 27  1  0  0  0  0
  9 10  2  0  0  0  0
 27 26  2  0  0  0  0
 26 25  1  0  0  0  0
 18 20  2  0  0  0  0
 27 28  1  0  0  0  0
 29 30  1  0  0  0  0
 20 22  1  0  0  0  0
 31 32  1  0  0  0  0
 10 12  1  0  0  0  0
 22 23  1  0  0  0  0
  9 38  1  0  0  0  0
 12 40  1  0  0  0  0
  5 35  1  0  0  0  0
  5 36  1  0  0  0  0
  4 34  1  6  0  0  0
 15 41  1  1  0  0  0
 17 42  1  0  0  0  0
 24 46  1  0  0  0  0
 11 39  1  0  0  0  0
  8 37  1  0  0  0  0
 21 44  1  0  0  0  0
 19 43  1  0  0  0  0
 33 51  1  0  0  0  0
 26 47  1  0  0  0  0
 28 48  1  0  0  0  0
 30 49  1  0  0  0  0
 32 50  1  0  0  0  0
 23 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031143

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(O[C@]([H])(C3=C([H])C(O[H])=C(O[H])C(O[H])=C3[H])[C@]([H])(OC(=O)C3=C([H])C(O[H])=C(O[H])C(O[H])=C3[H])C2([H])[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/m1/s1

> <INCHI_KEY>
WMBWREPUVVBILR-WIYYLYMNSA-N

> <FORMULA>
C22H18O11

> <MOLECULAR_WEIGHT>
458.3717

> <EXACT_MASS>
458.084911418

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
43.269253647488036

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
2.38

> <JCHEM_LOGP>
3.0761455773333326

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.719241714639647

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.992993558286566

> <JCHEM_PKA_STRONGEST_BASIC>
-5.423934990004846

> <JCHEM_POLAR_SURFACE_AREA>
197.36999999999998

> <JCHEM_REFRACTIVITY>
111.74530000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-epigallocatechin gallate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
   -1.1216    0.7525   -2.0020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5275    1.0574   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2562    0.2371    0.0584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6553   -1.1480   -0.0899 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1166   -1.3123    0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2696   -1.3205    1.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5327   -1.1798    2.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6234   -1.0481    1.6001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6887   -1.1726    3.7984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5676   -1.3121    4.6065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7535   -1.2945    5.9578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3029   -1.4692    4.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1598   -1.4898    2.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1203   -1.6544    2.2043 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2173   -2.0319    0.8201 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6816   -1.9843    0.4037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1821   -2.9424   -0.4974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5087   -2.8830   -0.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9826   -3.8184   -1.7793 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3464   -1.8811   -0.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6473   -1.8456   -0.8618 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8658   -0.9249    0.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7297    0.0470    0.8692 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5419   -0.9698    0.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0314    2.4120   -0.7291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6762    2.7403    0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2040    4.0135    0.6383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8455    4.3272    1.8014 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0876    4.9608   -0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6177    6.2069   -0.1749 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4426    4.6439   -1.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3585    5.6164   -2.5164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0876    3.3725   -1.7506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5262   -1.4533   -1.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7200   -0.5030   -0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4974   -2.2675   -0.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4151   -0.9449    2.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6639   -1.0589    4.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8895   -1.3956    6.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4233   -1.5852    4.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1141   -3.0783    0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5467   -3.7347   -0.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9208   -3.5733   -1.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0241   -1.0672   -0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2397    0.6548    1.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1603   -0.2239    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7707    2.0219    1.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1067    5.2652    1.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4150    6.6884   -1.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1148    5.2519   -3.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5883    3.1105   -2.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 24  2  0
 24 16  1  0
 12 13  2  0
 10 11  1  0
 13 14  1  0
  7  8  1  0
  6  5  1  0
  4  3  1  0
  5  4  1  0
 20 21  1  0
  4 15  1  0
 18 19  1  0
 15 14  1  0
  3  2  1  0
 13  6  1  0
  2  1  2  0
 15 16  1  0
  2 25  1  0
  7  9  1  0
 25 33  2  0
 16 17  2  0
 33 31  1  0
  6  7  2  0
 31 29  2  0
 17 18  1  0
 29 27  1  0
  9 10  2  0
 27 26  2  0
 26 25  1  0
 18 20  2  0
 27 28  1  0
 29 30  1  0
 20 22  1  0
 31 32  1  0
 10 12  1  0
 22 23  1  0
  9 38  1  0
 12 40  1  0
  5 35  1  0
  5 36  1  0
  4 34  1  6
 15 41  1  1
 17 42  1  0
 24 46  1  0
 11 39  1  0
  8 37  1  0
 21 44  1  0
 19 43  1  0
 33 51  1  0
 26 47  1  0
 28 48  1  0
 30 49  1  0
 32 50  1  0
 23 45  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  O   UNK     0      -1.122   0.753  -2.002  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.528   1.057  -0.981  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.256   0.237   0.058  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.655  -1.148  -0.090  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.117  -1.312   0.327  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.270  -1.321   1.826  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.533  -1.180   2.414  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.623  -1.048   1.600  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.689  -1.173   3.798  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.568  -1.312   4.606  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.753  -1.295   5.958  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.303  -1.469   4.051  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.160  -1.490   2.662  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.120  -1.654   2.204  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.217  -2.032   0.820  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.682  -1.984   0.404  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.182  -2.942  -0.497  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.509  -2.883  -0.906  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.983  -3.818  -1.779  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.346  -1.881  -0.437  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.647  -1.846  -0.862  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.866  -0.925   0.448  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.730   0.047   0.869  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.542  -0.970   0.874  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.031   2.412  -0.729  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.676   2.740   0.475  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.204   4.013   0.638  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.845   4.327   1.801  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.088   4.961  -0.370  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.618   6.207  -0.175  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.443   4.644  -1.560  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.359   5.616  -2.516  0.00  0.00           O+0
HETATM   33  C   UNK     0      -0.088   3.373  -1.751  0.00  0.00           C+0
HETATM   34  H   UNK     0      -0.526  -1.453  -1.137  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.720  -0.503  -0.099  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.497  -2.268  -0.055  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.415  -0.945   2.154  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.664  -1.059   4.260  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.890  -1.396   6.391  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.423  -1.585   4.676  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.114  -3.078   0.751  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.547  -3.735  -0.885  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.921  -3.573  -1.913  0.00  0.00           H+0
HETATM   44  H   UNK     0       6.024  -1.067  -0.402  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.240   0.655   1.452  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.160  -0.224   1.566  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.771   2.022   1.283  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.107   5.265   1.694  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.415   6.688  -1.004  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.115   5.252  -3.286  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.588   3.111  -2.679  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    3    1   25                                                  
CONECT    3    4    2                                                       
CONECT    4    3    5   15   34                                             
CONECT    5    6    4   35   36                                             
CONECT    6    5   13    7                                                  
CONECT    7    8    9    6                                                  
CONECT    8    7   37                                                       
CONECT    9    7   10   38                                                  
CONECT   10   11    9   12                                                  
CONECT   11   10   39                                                       
CONECT   12   13   10   40                                                  
CONECT   13   12   14    6                                                  
CONECT   14   13   15                                                       
CONECT   15    4   14   16   41                                             
CONECT   16   24   15   17                                                  
CONECT   17   16   18   42                                                  
CONECT   18   19   17   20                                                  
CONECT   19   18   43                                                       
CONECT   20   21   18   22                                                  
CONECT   21   20   44                                                       
CONECT   22   24   20   23                                                  
CONECT   23   22   45                                                       
CONECT   24   22   16   46                                                  
CONECT   25    2   33   26                                                  
CONECT   26   27   25   47                                                  
CONECT   27   29   26   28                                                  
CONECT   28   27   48                                                       
CONECT   29   31   27   30                                                  
CONECT   30   29   49                                                       
CONECT   31   33   29   32                                                  
CONECT   32   31   50                                                       
CONECT   33   25   31   51                                                  
CONECT   34    4                                                            
CONECT   35    5                                                            
CONECT   36    5                                                            
CONECT   37    8                                                            
CONECT   38    9                                                            
CONECT   39   11                                                            
CONECT   40   12                                                            
CONECT   41   15                                                            
CONECT   42   17                                                            
CONECT   43   19                                                            
CONECT   44   21                                                            
CONECT   45   23                                                            
CONECT   46   24                                                            
CONECT   47   26                                                            
CONECT   48   28                                                            
CONECT   49   30                                                            
CONECT   50   32                                                            
CONECT   51   33                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  108    0
END

RDKit          3D

51 54  0  0  0  0  0  0  0  0999 V2000
   -1.1216    0.7525   -2.0020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5275    1.0574   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2562    0.2371    0.0584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6553   -1.1480   -0.0899 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1166   -1.3123    0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2696   -1.3205    1.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5327   -1.1798    2.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6234   -1.0481    1.6001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6887   -1.1726    3.7984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5676   -1.3121    4.6065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7535   -1.2945    5.9578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3029   -1.4692    4.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1598   -1.4898    2.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1203   -1.6544    2.2043 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2173   -2.0319    0.8201 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6816   -1.9843    0.4037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1821   -2.9424   -0.4974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5087   -2.8830   -0.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9826   -3.8184   -1.7793 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3464   -1.8811   -0.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6473   -1.8456   -0.8618 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8658   -0.9249    0.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7297    0.0470    0.8692 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5419   -0.9698    0.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0314    2.4120   -0.7291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6762    2.7403    0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2040    4.0135    0.6383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8455    4.3272    1.8014 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0876    4.9608   -0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6177    6.2069   -0.1749 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4426    4.6439   -1.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3585    5.6164   -2.5164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0876    3.3725   -1.7506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5262   -1.4533   -1.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7200   -0.5030   -0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4974   -2.2675   -0.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4151   -0.9449    2.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6639   -1.0589    4.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8895   -1.3956    6.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4233   -1.5852    4.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1141   -3.0783    0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5467   -3.7347   -0.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9208   -3.5733   -1.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0241   -1.0672   -0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2397    0.6548    1.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1603   -0.2239    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7707    2.0219    1.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1067    5.2652    1.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4150    6.6884   -1.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1148    5.2519   -3.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5883    3.1105   -2.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 24  2  0
 24 16  1  0
 12 13  2  0
 10 11  1  0
 13 14  1  0
  7  8  1  0
  6  5  1  0
  4  3  1  0
  5  4  1  0
 20 21  1  0
  4 15  1  0
 18 19  1  0
 15 14  1  0
  3  2  1  0
 13  6  1  0
  2  1  2  0
 15 16  1  0
  2 25  1  0
  7  9  1  0
 25 33  2  0
 16 17  2  0
 33 31  1  0
  6  7  2  0
 31 29  2  0
 17 18  1  0
 29 27  1  0
  9 10  2  0
 27 26  2  0
 26 25  1  0
 18 20  2  0
 27 28  1  0
 29 30  1  0
 20 22  1  0
 31 32  1  0
 10 12  1  0
 22 23  1  0
  9 38  1  0
 12 40  1  0
  5 35  1  0
  5 36  1  0
  4 34  1  6
 15 41  1  1
 17 42  1  0
 24 46  1  0
 11 39  1  0
  8 37  1  0
 21 44  1  0
 19 43  1  0
 33 51  1  0
 26 47  1  0
 28 48  1  0
 30 49  1  0
 32 50  1  0
 23 45  1  0
M  END

View in JSmol

Synonyms

Value	Source
(-)-Epigallocatechin-3-O-gallate	ChEBI
[(2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate	ChEBI
EGCG	ChEBI
Epigallocatechin 3-gallate	ChEBI
(-)-Epigallocatechin-3-O-gallic acid	Generator
[(2R,3R)-5,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoic acid	Generator
Epigallocatechin 3-gallic acid	Generator
Epigallocatechin gallic acid	Generator
(-)-Epigallocatechin gallat	HMDB
(-)-Epigallocatechin gallate	HMDB
(-)-Epigallocatechol gallate	HMDB
(-)-Epigallocatehin gallate	HMDB
Catechin deriv.	HMDB
Epigallocatcchin gallate	HMDB
Epigallocate	HMDB
Epigallocic acid	HMDB
Galloyl-L-epigallocatechol	HMDB
Tea catechin	HMDB
Epigallo-catechin gallate	HMDB
Epigallocatechin-3-gallate	HMDB
Sunphenon	HMDB
EGCG CPD	HMDB
Epigallocatechin-3-O-gallate	HMDB

Chemical Formula

C₂₂H₁₈O₁₁

Average Mass

458.3717 Da

Monoisotopic Mass

458.08491 Da

IUPAC Name

(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

Traditional Name

(-)-epigallocatechin gallate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(O[H])=C2C(O[C@]([H])(C3=C([H])C(O[H])=C(O[H])C(O[H])=C3[H])[C@]([H])(OC(=O)C3=C([H])C(O[H])=C(O[H])C(O[H])=C3[H])C2([H])[H])=C1[H]

InChI Identifier

InChI=1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/m1/s1

InChI Key

WMBWREPUVVBILR-WIYYLYMNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6 at 303K, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acacia polyacantha	LOTUS Database	35616633
Acacia pycnantha	KNApSAcK Database	22123792
Alhagi sparsifolia	LOTUS Database	35616633
Alnus sieboldiana	LOTUS Database	35616633
Averrhoa carambola	Plant	KNApSAcK
Averrhoa carambola L.	KNApSAcK Database	22123792
Camellia crassicolumna	LOTUS Database	35616633
Camellia sinensis	KNApSAcK Database	22123792
Camellia taliensis	LOTUS Database	35616633
Cistus incanus	KNApSAcK Database	22123792
Cistus salviifolius	KNApSAcK Database	22123792
Coccoloba mollis	LOTUS Database	35616633
Cucurbita pepo	LOTUS Database	35616633
Davidsonia pruriens	KNApSAcK Database	22123792
Diospyros kaki	LOTUS Database	35616633
Eschweilera coriacea	LOTUS Database	35616633
Eskemukerjea megacarpum HARA	KNApSAcK Database	22123792
Eugenia edulis	KNApSAcK Database	22123792
Eugenia myrcianthes	LOTUS Database	35616633
Eugenia selloi	LOTUS Database	35616633
Euphorbia hirta	LOTUS Database	35616633
Fagopyrum megacarpum	LOTUS Database	35616633
Hamamelis virginiana	KNApSAcK Database	22123792
Hibiscus cannabinus	LOTUS Database	35616633
Hippophae rhamnoides	Plant	KNApSAcK
Limoniastrum guyonianum	LOTUS Database	35616633
Limonium gmelinii	LOTUS Database	35616633
Limonium sinense	LOTUS Database	35616633
Lotus corniculatus	LOTUS Database	35616633
Mallotus japonicus	KNApSAcK Database	22123792
Matricaria chamomilla	LOTUS Database	35616633
Morella esculenta	Plant	KNApSAcK
Morella rubra	Plant	KNApSAcK
Morus alba	LOTUS Database	35616633
Myrica esculenta	KNApSAcK Database	22123792
Myrica rubra	KNApSAcK Database	22123792
Myrtus communis	LOTUS Database	35616633
Parapiptadenia rigida	LOTUS Database	35616633
Parkia biglobosa	LOTUS Database	35616633
Phyllanthus emblica	KNApSAcK Database	22123792
Phyllanthus niruri	LOTUS Database	35616633
Platycarya strobilacea	LOTUS Database	35616633
Polygonum panjutinii	Plant	KNApSAcK
Potentilla fruticosa	LOTUS Database	35616633
Prunus dulcis	LOTUS Database	35616633
Pteroxygonum giraldii	LOTUS Database	35616633
Quercus robur	LOTUS Database	35616633
Rhodiola crenulata	LOTUS Database	35616633
Rhodiola heterodonta	LOTUS Database	35616633
Rhodiola kirilowii	LOTUS Database	35616633
Rhodiola sacra	LOTUS Database	35616633
Rhodiola semenovii	LOTUS Database	35616633
Rhododendron brachycarpum ssp.brachycarpum	KNApSAcK Database	22123792
Rhododendron catawbiense	KNApSAcK Database	22123792
Rhododendron Cunningham's white	KNApSAcK Database	22123792
Rhododendron ponticum	Plant	KNApSAcK
Rhododendron smirnowii	KNApSAcK Database	22123792
Rhododendron ungernii	KNApSAcK Database	22123792
Rosa rugosa	LOTUS Database	35616633
Sclerocarya birrea	LOTUS Database	35616633
Scurrula atropurpurea	KNApSAcK Database	22123792
Sedum crassularia	LOTUS Database	35616633
Sedum sediforme	KNApSAcK Database	22123792
Sempervivum tectorum	LOTUS Database	35616633
Sideroxylon inerme	LOTUS Database	35616633
Sideroxylon inerme L.	KNApSAcK Database	22123792
Stryphnodendron adstringens	KNApSAcK Database	22123792
Syzygium samarangense	KNApSAcK Database	22123792
Terminalia catappa	LOTUS Database	35616633
Thea sinensis	KNApSAcK Database	22123792
Theobroma cacao	LOTUS Database	35616633
Trifolium pratense	Plant	KNApSAcK
Turnera ulmifolia	Plant	KNApSAcK
Uncaria guianensis	LOTUS Database	35616633
Vitellaria paradoxa	LOTUS Database	35616633
Vitis vinifera	KNApSAcK Database	22123792
Vitis vinifera L.	Plant	KNApSAcK
Ziziphus jujuba	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Catechin gallates

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	222.00 to 224.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	909.00 to 910.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	32.77 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.639 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	2.38	ALOGPS
logP	3.08	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	7.99	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	197.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	111.75 m³·mol⁻¹	ChemAxon
Polarizability	43.27 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0003153

DrugBank ID

DB12116

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Epigallocatechin_gallate

METLIN ID

3550

PubChem Compound

65064

PDB ID

Not Available

ChEBI ID

4806

Good Scents ID

rw1654041

References

General References

Henning SM, Aronson W, Niu Y, Conde F, Lee NH, Seeram NP, Lee RP, Lu J, Harris DM, Moro A, Hong J, Pak-Shan L, Barnard RJ, Ziaee HG, Csathy G, Go VL, Wang H, Heber D: Tea polyphenols and theaflavins are present in prostate tissue of humans and mice after green and black tea consumption. J Nutr. 2006 Jul;136(7):1839-43. [PubMed:16772446 ]
Lill G, Voit S, Schror K, Weber AA: Complex effects of different green tea catechins on human platelets. FEBS Lett. 2003 Jul 10;546(2-3):265-70. [PubMed:12832052 ]
Uchida S, Ozaki M, Suzuki K, Shikita M: Radioprotective effects of (-)-epigallocatechin 3-O-gallate (green-tea tannin) in mice. Life Sci. 1992;50(2):147-52. doi: 10.1016/0024-3205(92)90296-2. [PubMed:1731169 ]
Dashwood WM, Carter O, Al-Fageeh M, Li Q, Dashwood RH: Lysosomal trafficking of beta-catenin induced by the tea polyphenol epigallocatechin-3-gallate. Mutat Res. 2005 Dec 11;591(1-2):161-72. doi: 10.1016/j.mrfmmm.2005.03.029. Epub 2005 Jul 27. [PubMed:16054165 ]
Dorchies OM, Wagner S, Vuadens O, Waldhauser K, Buetler TM, Kucera P, Ruegg UT: Green tea extract and its major polyphenol (-)-epigallocatechin gallate improve muscle function in a mouse model for Duchenne muscular dystrophy. Am J Physiol Cell Physiol. 2006 Feb;290(2):C616-25. doi: 10.1152/ajpcell.00425.2005. [PubMed:16403950 ]
Davis, A. L., et al. (1996). Davis, A. L., et al, Magn. Reson. Chem. 34, 887 (1996). Mag. Reson. Chem..

Showing NP-Card for epigallocatechin-3-O-gallate (NP0031143)

MOL for NP0031143 (epigallocatechin-3-O-gallate)

3D MOL for NP0031143 (epigallocatechin-3-O-gallate)

3D SDF for NP0031143 (epigallocatechin-3-O-gallate)

3D-SDF for NP0031143 (epigallocatechin-3-O-gallate)

PDB for NP0031143 (epigallocatechin-3-O-gallate)

3D PDB for NP0031143 (epigallocatechin-3-O-gallate)

SMILES for NP0031143 (epigallocatechin-3-O-gallate)

INCHI for NP0031143 (epigallocatechin-3-O-gallate)

Structure for NP0031143 (epigallocatechin-3-O-gallate)

3D Structure for NP0031143 (epigallocatechin-3-O-gallate)