NP-MRD: Showing NP-Card for Epiafzelechin 3-O-gallate (NP0056105)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 01:59:07 UTC

Updated at

2022-04-28 01:59:07 UTC

NP-MRD ID

NP0056105

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Epiafzelechin 3-O-gallate

Description

(-)-Epiafzelechin 3-gallate, also known as epiafzelechin 3-O-gallic acid, belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4. A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epiafzelechin (-)-Epiafzelechin 3-gallate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, (-)-Epiafzelechin 3-gallate is found, on average, in the highest concentration within tea. Epiafzelechin 3-O-gallate is found in Camellia sinensis and Camellia sinensis var. assamica . This could make (-)-epiafzelechin 3-gallate a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241211082D          

 31 34  0  0  0  0            999 V2000
   -2.0109   -3.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0109   -3.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -4.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5820   -3.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5820   -3.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1325   -2.5928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1325   -4.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8470   -3.8304    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8470   -3.0053    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5614   -2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2759   -1.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5614   -1.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2759   -3.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9904   -2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9904   -1.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7048   -1.3553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7254   -2.5929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -5.0679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9903   -5.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2759   -5.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2759   -6.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9903   -6.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7048   -6.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7048   -5.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4193   -5.0679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4193   -6.7179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9903   -7.5429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5614   -5.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8469   -5.4804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5614   -4.2429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 19  1  2  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
 19  5  1  0  0  0  0
  6  5  1  0  0  0  0
  5  4  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  6  0  0  0
 12 10  2  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 11 15  2  0  0  0  0
 15 16  1  0  0  0  0
  8 31  1  6  0  0  0
  1 17  1  0  0  0  0
  3 18  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 23 28  1  0  0  0  0
 21 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
M  END

     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
    1.7080   -1.7555    1.1111 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7658   -0.6501    0.4764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5764   -0.2279   -0.0732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5944   -0.9595    0.0598 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1347   -1.4726   -1.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2694   -2.3726   -0.9485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4841   -3.5981   -1.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6478   -4.1140   -2.5118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5904   -4.3841   -1.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4568   -3.9249   -0.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5339   -4.6981    0.1443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2254   -2.7031    0.3639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1473   -1.9073    0.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9259   -0.6662    0.6156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6173   -0.1730    0.8332 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5124    1.2899    0.6340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8163    2.0990    1.5353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7168    3.4590    1.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3018    4.0793    0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2038    5.4643    0.0835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9928    3.2879   -0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0876    1.9357   -0.4382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0141    0.0847    0.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1493   -0.4225    0.9465 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3618    0.2743    0.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5368   -0.1909    1.4153 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4182    1.4724    0.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6321    2.1528    0.0636 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2907    1.9775   -0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3754    3.1794   -1.1108 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1005    1.2764   -0.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3740   -1.8722    0.6522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3463   -2.0439   -1.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5400   -0.6499   -1.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8576   -3.5846   -2.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7133   -5.3371   -1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2265   -4.4539    0.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9093   -2.3430    1.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4253   -0.3423    1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3659    1.5882    2.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1785    4.0808    2.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8935    6.1034    0.4704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4536    3.7885   -1.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6371    1.3508   -1.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1914   -1.3447    1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5750   -1.0517    1.9304 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6985    3.0231   -0.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5784    3.6141   -1.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2073    1.6627   -0.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17 16  2  0
 16 22  1  0
 22 21  2  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13  6  2  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 21 19  1  0
  4 15  1  0
 31 23  1  0
 12 13  1  0
 20 42  1  0
 18 41  1  0
 17 40  1  0
 22 44  1  0
 21 43  1  0
 15 39  1  1
  5 33  1  0
  5 34  1  0
  4 32  1  1
 24 45  1  0
 26 46  1  0
 28 47  1  0
 30 48  1  0
 31 49  1  0
  8 35  1  0
  9 36  1  0
 11 37  1  0
 12 38  1  0
M  END


  Mrv0541 02241211082D          

 31 34  0  0  0  0            999 V2000
   -2.0109   -3.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0109   -3.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -4.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5820   -3.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5820   -3.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1325   -2.5928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1325   -4.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8470   -3.8304    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8470   -3.0053    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5614   -2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2759   -1.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5614   -1.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2759   -3.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9904   -2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9904   -1.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7048   -1.3553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7254   -2.5929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -5.0679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9903   -5.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2759   -5.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2759   -6.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9903   -6.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7048   -6.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7048   -5.4804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4193   -5.0679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4193   -6.7179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9903   -7.5429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5614   -5.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8469   -5.4804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5614   -4.2429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 19  1  2  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
 19  5  1  0  0  0  0
  6  5  1  0  0  0  0
  5  4  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  6  0  0  0
 12 10  2  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 11 15  2  0  0  0  0
 15 16  1  0  0  0  0
  8 31  1  6  0  0  0
  1 17  1  0  0  0  0
  3 18  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 23 28  1  0  0  0  0
 21 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056105

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)[C@H]1OC2=C(C[C@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1)C(O)=CC(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C22H18O9/c23-12-3-1-10(2-4-12)21-19(9-14-15(25)7-13(24)8-18(14)30-21)31-22(29)11-5-16(26)20(28)17(27)6-11/h1-8,19,21,23-28H,9H2/t19-,21-/m1/s1

> <INCHI_KEY>
SDZPYNMXGUHFMZ-TZIWHRDSSA-N

> <FORMULA>
C22H18O9

> <MOLECULAR_WEIGHT>
426.3729

> <EXACT_MASS>
426.095082174

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
41.2512128416905

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.74

> <JCHEM_LOGP>
3.683276220666666

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.984331764297282

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.045641003480604

> <JCHEM_PKA_STRONGEST_BASIC>
-4.919154545583639

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
107.78349999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
epiafzelechin 3-O-gallate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.754  -5.610   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.754  -7.150   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.420  -7.920   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.086  -7.150   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.086  -5.610   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.247  -4.840   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.247  -7.920   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.581  -7.150   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.581  -5.610   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.915  -4.840   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.248  -2.530   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.915  -3.300   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.248  -5.610   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.582  -4.840   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.582  -3.300   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.916  -2.530   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -5.087  -4.840   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.420  -9.460   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.420  -4.840   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.582  -9.460   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.248 -10.230   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.248 -11.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.582 -12.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.916 -11.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.916 -10.230   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.249  -9.460   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       8.249 -12.540   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.582 -14.080   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.915  -9.460   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.581 -10.230   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       2.915  -7.920   0.000  0.00  0.00           O+0
CONECT    1   19    2   17                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5    7                                                  
CONECT    5   19    6    4                                                  
CONECT    6    5    9                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   31                                                  
CONECT    9    8    6   10                                                  
CONECT   10    9   12   13                                                  
CONECT   11   12   15                                                       
CONECT   12   10   11                                                       
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11   16                                                  
CONECT   16   15                                                            
CONECT   17    1                                                            
CONECT   18    3                                                            
CONECT   19    1    5                                                       
CONECT   20   21   25                                                       
CONECT   21   20   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25   27                                                  
CONECT   25   24   20   26                                                  
CONECT   26   25                                                            
CONECT   27   24                                                            
CONECT   28   23                                                            
CONECT   29   21   30   31                                                  
CONECT   30   29                                                            
CONECT   31    8   29                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
(-)-Epiafzelechin 3-O-gallate	ChEBI
Epiafzelechin 3-O-gallate	ChEBI
(-)-Epiafzelechin 3-O-gallic acid	Generator
Epiafzelechin 3-O-gallic acid	Generator
(-)-Epiafzelechin 3-gallic acid	Generator
(-)-Epiafzelechin gallate	HMDB
(-)-Epiafzelechin gallic acid	HMDB
3-Galloyl-(-)-epiafzelechin	HMDB
(-)-Epiafzelechin 3-gallate	ChEBI

Chemical Formula

C₂₂H₁₈O₉

Average Mass

426.3729 Da

Monoisotopic Mass

426.09508 Da

IUPAC Name

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

Traditional Name

epiafzelechin 3-O-gallate

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)[C@H]1OC2=C(C[C@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1)C(O)=CC(O)=C2

InChI Identifier

InChI=1S/C22H18O9/c23-12-3-1-10(2-4-12)21-19(9-14-15(25)7-13(24)8-18(14)30-21)31-22(29)11-5-16(26)20(28)17(27)6-11/h1-8,19,21,23-28H,9H2/t19-,21-/m1/s1

InChI Key

SDZPYNMXGUHFMZ-TZIWHRDSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Camellia sinensis	LOTUS Database	35616633
Camellia sinensis var. assamica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavan-3-ols

Alternative Parents

Substituents

Flavan-3-ol
Hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Chromane
Benzopyran
1-benzopyran
Benzoate ester
Pyrogallol derivative
Benzoic acid or derivatives
Benzenetriol
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavans, Flavanols and Leucoanthocyanidins (LMPK12020038 )

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	2.74	ALOGPS
logP	3.68	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	8.05	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.78 m³·mol⁻¹	ChemAxon
Polarizability	41.25 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

HMDB0038846

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018281

KNApSAcK ID

C00008864

Chemspider ID

410660

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

467295

PDB ID

Not Available

ChEBI ID

136552

Good Scents ID

Not Available

References

General References

Showing NP-Card for Epiafzelechin 3-O-gallate (NP0056105)

MOL for NP0056105 (Epiafzelechin 3-O-gallate)

3D MOL for NP0056105 (Epiafzelechin 3-O-gallate)

3D SDF for NP0056105 (Epiafzelechin 3-O-gallate)

3D-SDF for NP0056105 (Epiafzelechin 3-O-gallate)

PDB for NP0056105 (Epiafzelechin 3-O-gallate)

3D PDB for NP0056105 (Epiafzelechin 3-O-gallate)

SMILES for NP0056105 (Epiafzelechin 3-O-gallate)

INCHI for NP0056105 (Epiafzelechin 3-O-gallate)

Structure for NP0056105 (Epiafzelechin 3-O-gallate)

3D Structure for NP0056105 (Epiafzelechin 3-O-gallate)