NP-MRD: Showing NP-Card for gallocatechin 3-o-gallate (NP0294463)

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Record Information

Version

2.0

Created at

2022-09-10 03:00:28 UTC

Updated at

2022-09-10 03:00:28 UTC

NP-MRD ID

NP0294463

Secondary Accession Numbers

None

Natural Product Identification

Common Name

gallocatechin 3-o-gallate

Description

3-Galloylgallocatechin, also known as gallocatechin 3-gallate, belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin. 3-Galloylgallocatechin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 3-Galloylgallocatechin is found, on average, in the highest concentration within a few different foods, such as tea, pecan nuts, and pistachio and in a lower concentration in almonds, common hazelnuts, and german camomiles. 3-Galloylgallocatechin has also been detected, but not quantified in, several different foods, such as peanuts, pine nuts, macadamia nut (m. Tetraphylla), brazil nuts, and peppermints. gallocatechin 3-o-gallate is found in Anacardium occidentale, Camellia sinensis, Cistus incanus, Matricaria chamomilla and Vitis vinifera. This could make 3-galloylgallocatechin a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241221532D          

 33 36  0  0  1  0            999 V2000
    2.1080  -13.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8183  -13.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3942  -13.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8114  -14.7566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287  -13.5360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3907  -14.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5149  -15.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1011  -15.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2356  -13.9497    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2287  -14.7705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1011  -15.9981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9597  -13.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6736  -13.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9631  -12.7118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3943  -13.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6874  -12.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4012  -12.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1219  -12.3117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6817  -13.5165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1050  -13.9721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9403  -15.1879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9345  -16.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2172  -16.4205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6462  -16.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6403  -17.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3519  -17.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0692  -17.2645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0749  -16.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3633  -16.0221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7808  -17.6820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7923  -16.0320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3461  -18.4970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6959  -11.4762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  6  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  2  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
  6  8  1  0  0  0  0
  9 10  1  0  0  0  0
 16 17  1  0  0  0  0
  3 19  1  0  0  0  0
 15 20  1  0  0  0  0
 10 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 24  1  0  0  0  0
 27 30  1  0  0  0  0
 28 31  1  0  0  0  0
 26 32  1  0  0  0  0
 16 33  1  0  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
    1.6316   -1.3418    1.5533 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8844   -0.5825    0.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8412    0.2099    0.1673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4549    0.2124    0.7047 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8297    1.5073    1.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4306    2.4854    0.4507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1791    3.8256    0.5733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3462    4.2897    1.5743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7429    4.7475   -0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5698    4.2586   -1.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1358    5.1956   -2.1471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8442    2.9075   -1.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2575    2.0283   -0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4634    0.6564   -0.6027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4630   -0.2841   -0.2800 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1539   -1.5241    0.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7923   -2.7728   -0.2671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4773   -3.9160    0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0861   -5.1641   -0.2733 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5337   -3.8138    1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2726   -4.8789    1.5338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9006   -2.5304    1.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9789   -2.4248    2.3598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2129   -1.4289    1.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2200   -0.5167   -0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4694    0.3360   -1.0683 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7240    0.4177   -1.6819 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9228    1.2968   -2.7370 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7354   -0.4049   -1.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9926   -0.3749   -1.7514 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5111   -1.2727   -0.1407 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5620   -2.0651    0.2973 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2587   -1.3062    0.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4175   -0.5553    1.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0306    1.8793    1.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6228    1.2646    2.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1193    5.2542    1.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5630    5.8112   -0.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5811    5.3982   -2.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4947    2.5434   -2.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9157   -0.5652   -1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9726   -2.8818   -0.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5486   -5.9931    0.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0480   -5.8099    1.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2265   -1.4906    2.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5186   -0.4394    1.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6556    0.9722   -1.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8227    1.3546   -3.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3233    0.1797   -2.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5177   -2.7204    1.0406 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0504   -1.9738    1.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  9  2  0
  9  7  1  0
  7  8  1  0
  7  6  2  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  2  0
  4 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  2  0
 12 10  1  0
 24 16  1  0
 13  6  1  0
 33 25  1  0
 11 39  1  0
  9 38  1  0
  8 37  1  0
  5 35  1  0
  5 36  1  0
  4 34  1  1
 26 47  1  0
 28 48  1  0
 30 49  1  0
 32 50  1  0
 33 51  1  0
 15 41  1  6
 12 40  1  0
 17 42  1  0
 19 43  1  0
 21 44  1  0
 23 45  1  0
 24 46  1  0
M  END


  Mrv0541 02241221532D          

 33 36  0  0  1  0            999 V2000
    2.1080  -13.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8183  -13.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3942  -13.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8114  -14.7566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287  -13.5360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3907  -14.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5149  -15.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1011  -15.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2356  -13.9497    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2287  -14.7705    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1011  -15.9981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9597  -13.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6736  -13.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9631  -12.7118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3943  -13.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6874  -12.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4012  -12.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1219  -12.3117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6817  -13.5165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1050  -13.9721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9403  -15.1879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9345  -16.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2172  -16.4205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6462  -16.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6403  -17.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3519  -17.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0692  -17.2645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0749  -16.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3633  -16.0221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7808  -17.6820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7923  -16.0320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3461  -18.4970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6959  -11.4762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  6  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  2  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
  6  8  1  0  0  0  0
  9 10  1  0  0  0  0
 16 17  1  0  0  0  0
  3 19  1  0  0  0  0
 15 20  1  0  0  0  0
 10 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 24  1  0  0  0  0
 27 30  1  0  0  0  0
 28 31  1  0  0  0  0
 26 32  1  0  0  0  0
 16 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0294463

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C2C[C@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC2=C1)C1=CC(O)=C(O)C(O)=C1

> <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+/m0/s1

> <INCHI_KEY>
WMBWREPUVVBILR-GHTZIAJQSA-N

> <FORMULA>
C22H18O11

> <MOLECULAR_WEIGHT>
458.3717

> <EXACT_MASS>
458.084911418

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
42.868705283336034

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S)-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>
111.74529999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gallocatechin 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       3.935 -25.248   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.261 -26.014   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.603 -26.007   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.248 -27.546   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.587 -25.267   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.596 -27.539   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.561 -28.331   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.922 -28.318   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.906 -26.039   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.894 -27.572   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.922 -29.863   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.258 -25.280   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.591 -26.059   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.264 -23.729   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.936 -25.299   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.616 -22.963   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.949 -23.754   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      13.294 -22.982   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.273 -25.231   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      13.263 -26.081   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.222 -28.351   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.211 -29.891   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.872 -30.652   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.540 -30.670   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.529 -32.209   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.857 -32.988   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.196 -32.227   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.206 -30.687   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.878 -29.908   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      14.524 -33.006   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      14.546 -29.926   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      11.846 -34.528   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      10.632 -21.422   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4    5                                                  
CONECT    3    1    6   19                                                  
CONECT    4    2    7    8                                                  
CONECT    5    2    9                                                       
CONECT    6    3    8                                                       
CONECT    7    4   10                                                       
CONECT    8    4   11    6                                                  
CONECT    9    5   12   10                                                  
CONECT   10    7    9   21                                                  
CONECT   11    8                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17   20                                                  
CONECT   16   14   17   33                                                  
CONECT   17   15   18   16                                                  
CONECT   18   17                                                            
CONECT   19    3                                                            
CONECT   20   15                                                            
CONECT   21   10   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28   30                                                  
CONECT   28   27   29   31                                                  
CONECT   29   28   24                                                       
CONECT   30   27                                                            
CONECT   31   28                                                            
CONECT   32   26                                                            
CONECT   33   16                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(+)-Gallocatechin 3-O-gallate	HMDB
Gallocatechin 3-gallate	HMDB
Gallocatechin 3-O-gallate	HMDB
Gallocatechin-3-gallate	MeSH
Gallocatechin 3-O-gallic acid	Generator
Gallocatechin gallate	MeSH
Gallocatechin 3-gallic acid	Generator

Chemical Formula

C₂₂H₁₈O₁₁

Average Mass

458.3717 Da

Monoisotopic Mass

458.08491 Da

IUPAC Name

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

Traditional Name

gallocatechin 3-O-gallate

CAS Registry Number

Not Available

SMILES

OC1=CC(O)=C2C[C@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC2=C1)C1=CC(O)=C(O)C(O)=C1

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+/m0/s1

InChI Key

WMBWREPUVVBILR-GHTZIAJQSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Anacardium occidentale	LOTUS Database	35616633
Camellia sinensis	LOTUS Database	35616633
Cistus incanus	LOTUS Database	35616633
Matricaria chamomilla	LOTUS Database	35616633
Vitis vinifera	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
Epigallocatechin
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Chromane
Benzopyran
1-benzopyran
Pyrogallol derivative
Benzenetriol
Benzoic acid or derivatives
Benzoyl
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Carboxylic acid ester
Carboxylic acid derivative
Polyol
Oxacycle
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavans, Flavanols and Leucoanthocyanidins (LMPK12020120 )

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	2.38	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	42.87 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

HMDB0041598

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5276890

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for gallocatechin 3-o-gallate (NP0294463)

MOL for NP0294463 (gallocatechin 3-o-gallate)

3D MOL for NP0294463 (gallocatechin 3-o-gallate)

3D SDF for NP0294463 (gallocatechin 3-o-gallate)

3D-SDF for NP0294463 (gallocatechin 3-o-gallate)

PDB for NP0294463 (gallocatechin 3-o-gallate)

3D PDB for NP0294463 (gallocatechin 3-o-gallate)

SMILES for NP0294463 (gallocatechin 3-o-gallate)

INCHI for NP0294463 (gallocatechin 3-o-gallate)

Structure for NP0294463 (gallocatechin 3-o-gallate)

3D Structure for NP0294463 (gallocatechin 3-o-gallate)