NP-MRD: Showing NP-Card for epigallocatechin-3-O-(3'-O-methyl)gallate (NP0031145)

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Record Information

Version

2.0

Created at

2021-06-19 22:18:36 UTC

Updated at

2021-06-29 23:59:33 UTC

NP-MRD ID

NP0031145

Secondary Accession Numbers

None

Natural Product Identification

Common Name

epigallocatechin-3-O-(3'-O-methyl)gallate

Provided By

JEOL Database JEOL Logo

Description

(-)-Epigallocatechin 3-(3-methyl-gallate), also known as 3-O-(3-O-methylgalloyl)epigallocatechin or egcg3''me, 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 3-(3-methyl-gallate) is found, on average, in the highest concentration within a few different foods, such as teas (Camellia sinensis), red tea, and herbal tea and in a lower concentration in green tea and black tea. This could make (-)-epigallocatechin 3-(3-methyl-gallate) a potential biomarker for the consumption of these foods. epigallocatechin-3-O-(3'-O-methyl)gallate is found in Camellia sinensis and Limonium sinense. epigallocatechin-3-O-(3'-O-methyl)gallate was first documented in 1996 (Davis, A. L., et al.). Based on a literature review very few articles have been published on (-)-Epigallocatechin 3-(3-methyl-gallate).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100183D          

 54 57  0  0  0  0            999 V2000
   -1.1127   -2.9049   -0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4354   -3.2547    0.8274 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4328   -2.3205    1.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5866   -1.0102    0.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5276   -0.1553    1.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7286    1.2364    1.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7502    1.8782    1.1863 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6147    1.6737    0.3746 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1 37  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652306202100183D          

 54 57  0  0  0  0            999 V2000
   -1.1127   -2.9049   -0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4354   -3.2547    0.8274 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5276   -0.1553    1.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7286    1.2364    1.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7502    1.8782    1.1863 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7061   -3.7698   -0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067   -0.6359    0.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6942    3.1516   -0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7761    5.0319    0.5182 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9452    3.8067    1.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0317    5.8693    3.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2103    5.5555    3.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6337    4.0909    1.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0947    3.2897   -0.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3132    4.1526   -1.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4444    0.6190   -1.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7125   -1.6480   -4.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3918   -0.1187   -6.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3648    2.7276   -5.3335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3348    3.4484   -3.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0594    0.0330    3.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6244   -3.2891    4.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3975   -4.4392    2.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 21  1  0  0  0  0
 17 18  2  0  0  0  0
 15 16  1  0  0  0  0
 18 19  1  0  0  0  0
 12 13  1  0  0  0  0
 11 10  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 25 26  1  0  0  0  0
  9 20  1  0  0  0  0
 23 24  1  0  0  0  0
 20 19  1  0  0  0  0
  8  6  1  0  0  0  0
 18 11  1  0  0  0  0
  6  7  2  0  0  0  0
 20 21  1  0  0  0  0
  6  5  1  0  0  0  0
 12 14  1  0  0  0  0
  5 30  1  0  0  0  0
 21 22  2  0  0  0  0
 30 31  2  0  0  0  0
 11 12  2  0  0  0  0
 31 33  1  0  0  0  0
 22 23  1  0  0  0  0
 33  3  2  0  0  0  0
 14 15  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
 23 25  2  0  0  0  0
  3  2  1  0  0  0  0
 33 34  1  0  0  0  0
 25 27  1  0  0  0  0
 31 32  1  0  0  0  0
 15 17  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
  2  1  1  0  0  0  0
 14 43  1  0  0  0  0
 17 45  1  0  0  0  0
 10 40  1  0  0  0  0
 10 41  1  0  0  0  0
  9 39  1  6  0  0  0
 20 46  1  6  0  0  0
 22 47  1  0  0  0  0
 29 51  1  0  0  0  0
 16 44  1  0  0  0  0
 13 42  1  0  0  0  0
 26 49  1  0  0  0  0
 24 48  1  0  0  0  0
 30 52  1  0  0  0  0
  4 38  1  0  0  0  0
 34 54  1  0  0  0  0
 32 53  1  0  0  0  0
 28 50  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031145

> <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(OC([H])([H])[H])=C(O[H])C(O[H])=C3[H])C2([H])[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H20O11/c1-32-18-5-10(4-16(28)21(18)30)23(31)34-19-8-12-13(25)6-11(24)7-17(12)33-22(19)9-2-14(26)20(29)15(27)3-9/h2-7,19,22,24-30H,8H2,1H3/t19-,22-/m1/s1

> <INCHI_KEY>
WVRDOLPMKOCJRJ-DENIHFKCSA-N

> <FORMULA>
C23H20O11

> <MOLECULAR_WEIGHT>
472.3983

> <EXACT_MASS>
472.100561482

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
44.532458203728254

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <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-dihydroxy-5-methoxybenzoate

> <ALOGPS_LOGP>
2.66

> <JCHEM_LOGP>
3.2220396333333334

> <ALOGPS_LOGS>
-3.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.966120243953597

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.478292208597782

> <JCHEM_PKA_STRONGEST_BASIC>
-4.913037200943858

> <JCHEM_POLAR_SURFACE_AREA>
186.37

> <JCHEM_REFRACTIVITY>
116.2276

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.08e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -1.1127   -2.9049   -0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4354   -3.2547    0.8274 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4328   -2.3205    1.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5866   -1.0102    0.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5276   -0.1553    1.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7286    1.2364    1.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7502    1.8782    1.1863 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6147    1.6737    0.3746 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6904    3.0014   -0.1984 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4136    4.0586    0.8714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0579    4.1941    1.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5027    4.8960    2.2863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5733    5.4687    3.1093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8604    5.0171    2.5741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7872    4.4322    1.7210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1085    4.5623    2.0339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3761    3.7439    0.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0130    3.6418    0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7019    2.9540   -0.8424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588    3.1406   -1.3172 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0927    2.1573   -2.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7281    0.9000   -2.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4404    0.0011   -3.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0528   -1.2189   -3.5205 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4684    0.3347   -4.4987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7326   -0.5710   -5.4903 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1032    1.5706   -4.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9927    1.8410   -5.4827 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8332    2.4848   -3.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3222   -0.6140    2.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1531   -1.9124    2.9942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9151   -2.3645    4.0324 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2187   -2.7546    2.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0958   -4.0310    2.8876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8012   -2.0697   -0.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3997   -2.6833   -1.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7061   -3.7698   -0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067   -0.6359    0.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6942    3.1516   -0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7761    5.0319    0.5182 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9452    3.8067    1.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0317    5.8693    3.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2103    5.5555    3.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6337    4.0909    1.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0947    3.2897   -0.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3132    4.1526   -1.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4444    0.6190   -1.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7125   -1.6480   -4.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3918   -0.1187   -6.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3648    2.7276   -5.3335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3348    3.4484   -3.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0594    0.0330    3.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6244   -3.2891    4.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3975   -4.4392    2.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 21  1  0
 17 18  2  0
 15 16  1  0
 18 19  1  0
 12 13  1  0
 11 10  1  0
  9  8  1  0
 10  9  1  0
 25 26  1  0
  9 20  1  0
 23 24  1  0
 20 19  1  0
  8  6  1  0
 18 11  1  0
  6  7  2  0
 20 21  1  0
  6  5  1  0
 12 14  1  0
  5 30  1  0
 21 22  2  0
 30 31  2  0
 11 12  2  0
 31 33  1  0
 22 23  1  0
 33  3  2  0
 14 15  2  0
  3  4  1  0
  4  5  2  0
 23 25  2  0
  3  2  1  0
 33 34  1  0
 25 27  1  0
 31 32  1  0
 15 17  1  0
 27 28  1  0
 27 29  2  0
  2  1  1  0
 14 43  1  0
 17 45  1  0
 10 40  1  0
 10 41  1  0
  9 39  1  6
 20 46  1  6
 22 47  1  0
 29 51  1  0
 16 44  1  0
 13 42  1  0
 26 49  1  0
 24 48  1  0
 30 52  1  0
  4 38  1  0
 34 54  1  0
 32 53  1  0
 28 50  1  0
  1 35  1  0
  1 36  1  0
  1 37  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  C   UNK     0      -1.113  -2.905  -0.378  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.435  -3.255   0.827  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.433  -2.321   1.330  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.587  -1.010   0.876  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.528  -0.155   1.483  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.729   1.236   1.008  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.750   1.878   1.186  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.615   1.674   0.375  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.690   3.001  -0.198  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.414   4.059   0.871  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.058   4.194   1.159  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.503   4.896   2.286  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.573   5.469   3.109  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.860   5.017   2.574  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.787   4.432   1.721  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.109   4.562   2.034  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.376   3.744   0.585  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.013   3.642   0.299  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.702   2.954  -0.842  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.359   3.141  -1.317  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.093   2.157  -2.453  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.728   0.900  -2.489  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.440   0.001  -3.506  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.053  -1.219  -3.521  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.468   0.335  -4.499  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.733  -0.571  -5.490  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.103   1.571  -4.480  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.993   1.841  -5.483  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.833   2.485  -3.464  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.322  -0.614   2.541  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.153  -1.912   2.994  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.915  -2.365   4.032  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.219  -2.755   2.400  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.096  -4.031   2.888  0.00  0.00           O+0
HETATM   35  H   UNK     0      -1.801  -2.070  -0.214  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.400  -2.683  -1.178  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.706  -3.770  -0.689  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.007  -0.636   0.049  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.694   3.152  -0.618  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.776   5.032   0.518  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.945   3.807   1.796  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.032   5.869   3.867  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.210   5.556   3.449  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.634   4.091   1.366  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.095   3.290  -0.089  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.313   4.153  -1.745  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.444   0.619  -1.720  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.713  -1.648  -4.333  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.392  -0.119  -6.056  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.365   2.728  -5.333  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.335   3.448  -3.445  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.059   0.033   3.009  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.624  -3.289   4.169  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.398  -4.439   2.336  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2    3    1                                                       
CONECT    3   33    4    2                                                  
CONECT    4    3    5   38                                                  
CONECT    5    6   30    4                                                  
CONECT    6    8    7    5                                                  
CONECT    7    6                                                            
CONECT    8    9    6                                                       
CONECT    9    8   10   20   39                                             
CONECT   10   11    9   40   41                                             
CONECT   11   10   18   12                                                  
CONECT   12   13   14   11                                                  
CONECT   13   12   42                                                       
CONECT   14   12   15   43                                                  
CONECT   15   16   14   17                                                  
CONECT   16   15   44                                                       
CONECT   17   18   15   45                                                  
CONECT   18   17   19   11                                                  
CONECT   19   18   20                                                       
CONECT   20    9   19   21   46                                             
CONECT   21   29   20   22                                                  
CONECT   22   21   23   47                                                  
CONECT   23   24   22   25                                                  
CONECT   24   23   48                                                       
CONECT   25   26   23   27                                                  
CONECT   26   25   49                                                       
CONECT   27   25   28   29                                                  
CONECT   28   27   50                                                       
CONECT   29   21   27   51                                                  
CONECT   30    5   31   52                                                  
CONECT   31   30   33   32                                                  
CONECT   32   31   53                                                       
CONECT   33   31    3   34                                                  
CONECT   34   33   54                                                       
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    4                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   10                                                            
CONECT   42   13                                                            
CONECT   43   14                                                            
CONECT   44   16                                                            
CONECT   45   17                                                            
CONECT   46   20                                                            
CONECT   47   22                                                            
CONECT   48   24                                                            
CONECT   49   26                                                            
CONECT   50   28                                                            
CONECT   51   29                                                            
CONECT   52   30                                                            
CONECT   53   32                                                            
CONECT   54   34                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  114    0
END

RDKit          3D

54 57  0  0  0  0  0  0  0  0999 V2000
   -1.1127   -2.9049   -0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4354   -3.2547    0.8274 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4328   -2.3205    1.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5866   -1.0102    0.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5276   -0.1553    1.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7286    1.2364    1.0084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7502    1.8782    1.1863 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6147    1.6737    0.3746 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6904    3.0014   -0.1984 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4136    4.0586    0.8714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0579    4.1941    1.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5027    4.8960    2.2863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5733    5.4687    3.1093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8604    5.0171    2.5741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7872    4.4322    1.7210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1085    4.5623    2.0339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3761    3.7439    0.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0130    3.6418    0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7019    2.9540   -0.8424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588    3.1406   -1.3172 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0927    2.1573   -2.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7281    0.9000   -2.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4404    0.0011   -3.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0528   -1.2189   -3.5205 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4684    0.3347   -4.4987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7326   -0.5710   -5.4903 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1032    1.5706   -4.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9927    1.8410   -5.4827 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8332    2.4848   -3.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3222   -0.6140    2.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1531   -1.9124    2.9942 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9151   -2.3645    4.0324 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2187   -2.7546    2.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0958   -4.0310    2.8876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8012   -2.0697   -0.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3997   -2.6833   -1.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7061   -3.7698   -0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067   -0.6359    0.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6942    3.1516   -0.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7761    5.0319    0.5182 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9452    3.8067    1.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0317    5.8693    3.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2103    5.5555    3.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6337    4.0909    1.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0947    3.2897   -0.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3132    4.1526   -1.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4444    0.6190   -1.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7125   -1.6480   -4.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3918   -0.1187   -6.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3648    2.7276   -5.3335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3348    3.4484   -3.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0594    0.0330    3.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6244   -3.2891    4.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3975   -4.4392    2.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 21  1  0
 17 18  2  0
 15 16  1  0
 18 19  1  0
 12 13  1  0
 11 10  1  0
  9  8  1  0
 10  9  1  0
 25 26  1  0
  9 20  1  0
 23 24  1  0
 20 19  1  0
  8  6  1  0
 18 11  1  0
  6  7  2  0
 20 21  1  0
  6  5  1  0
 12 14  1  0
  5 30  1  0
 21 22  2  0
 30 31  2  0
 11 12  2  0
 31 33  1  0
 22 23  1  0
 33  3  2  0
 14 15  2  0
  3  4  1  0
  4  5  2  0
 23 25  2  0
  3  2  1  0
 33 34  1  0
 25 27  1  0
 31 32  1  0
 15 17  1  0
 27 28  1  0
 27 29  2  0
  2  1  1  0
 14 43  1  0
 17 45  1  0
 10 40  1  0
 10 41  1  0
  9 39  1  6
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 29 51  1  0
 16 44  1  0
 13 42  1  0
 26 49  1  0
 24 48  1  0
 30 52  1  0
  4 38  1  0
 34 54  1  0
 32 53  1  0
 28 50  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
M  END

View in JSmol

Synonyms

Value	Source
(-)-Epigallocatechin 3-(3-methyl-gallic acid)	Generator
3-O-(3-O-Methylgalloyl)epigallocatechin	HMDB
Epigallocatechin 3-(3-methyl-gallate)	HMDB
Epigallocatechin 3-(3-O-methyl-gallate)	HMDB
Epigallocatechin 3-O-(3-O-methylgallate)	HMDB
Epigallocatechin-3-O-(3''-O-methyl)-gallate	HMDB
Epigallocatechin 3-O-(3-O-methylgallic acid)	HMDB
EGCG3''me	HMDB
Epigallocatechin 3-(3-methylgallic acid)	Generator

Chemical Formula

C₂₃H₂₀O₁₁

Average Mass

472.3983 Da

Monoisotopic Mass

472.10056 Da

IUPAC Name

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

Traditional Name

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

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

InChI Identifier

InChI=1S/C23H20O11/c1-32-18-5-10(4-16(28)21(18)30)23(31)34-19-8-12-13(25)6-11(24)7-17(12)33-22(19)9-2-14(26)20(29)15(27)3-9/h2-7,19,22,24-30H,8H2,1H3/t19-,22-/m1/s1

InChI Key

WVRDOLPMKOCJRJ-DENIHFKCSA-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
Camellia sinensis	Plant	KNApSAcK
Limonium sinense	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

Substituents

Catechin gallate
Hydrolyzable tannin
Epigallocatechin
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Tannin
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Dihydroxybenzoic acid
M-methoxybenzoic acid or derivatives
Benzoate ester
Chromane
Benzopyran
1-benzopyran
Methoxyphenol
Pyrogallol derivative
Benzenetriol
Benzoic acid or derivatives
Phenol ether
Methoxybenzene
Anisole
Catechol
Phenoxy compound
Benzoyl
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Carboxylic acid ester
Monocarboxylic acid or derivatives
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavans, Flavanols and Leucoanthocyanidins (LMPK12020121 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.66	ALOGPS
logP	3.22	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.48	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	116.23 m³·mol⁻¹	ChemAxon
Polarizability	44.53 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

HMDB0038363

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017703

KNApSAcK ID

C00008883

Chemspider ID

7980602

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9804842

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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-(3'-O-methyl)gallate (NP0031145)

MOL for NP0031145 (epigallocatechin-3-O-(3'-O-methyl)gallate)

3D MOL for NP0031145 (epigallocatechin-3-O-(3'-O-methyl)gallate)

3D SDF for NP0031145 (epigallocatechin-3-O-(3'-O-methyl)gallate)

3D-SDF for NP0031145 (epigallocatechin-3-O-(3'-O-methyl)gallate)

PDB for NP0031145 (epigallocatechin-3-O-(3'-O-methyl)gallate)

3D PDB for NP0031145 (epigallocatechin-3-O-(3'-O-methyl)gallate)

SMILES for NP0031145 (epigallocatechin-3-O-(3'-O-methyl)gallate)

INCHI for NP0031145 (epigallocatechin-3-O-(3'-O-methyl)gallate)

Structure for NP0031145 (epigallocatechin-3-O-(3'-O-methyl)gallate)

3D Structure for NP0031145 (epigallocatechin-3-O-(3'-O-methyl)gallate)