NP-MRD: Showing NP-Card for Penta-O-galloyl-beta-D-glucose (NP0075653)

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Record Information

Version

2.0

Created at

2022-04-28 20:54:46 UTC

Updated at

2022-04-28 20:54:46 UTC

NP-MRD ID

NP0075653

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Penta-O-galloyl-beta-D-glucose

Description

1,2,3,4,6-Pentakis-O-galloyl-beta-D-glucose, also known as 1,2,3,4,6-PGG or pentagalloyl-beta-D-glucose, belongs to the class of organic compounds known as tannins. These are naturally occurring polyphenols which be categorized into four main classes: Hydrolyzable tannin (based on ellagic acid or gallic acid), condensed tannins (made of oligomeric or polymeric proanthocyanidins), complex tannins (made of a catechin bound to a gallotannin or elagitannin), and phlorotannins (oligomers of phloroglucinol). 1,2,3,4,6-Pentakis-O-galloyl-beta-D-glucose is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Penta-O-galloyl-beta-D-glucose is found in Acer truncatum, Agrobacterium rhizogenes, Caryocar villosum, Castanopsis fissa, Cercidiphyllum japonicum, Cornulaca monacantha , Cotinus coggygria, Cuphea hyssopifolia, Eucalyptus alba, Eucalyptus globulus, Euphorbia helioscopia, Euphorbia humifusa, Euphorbia jolkinii, Euphorbia maculata, Euphorbia thymifolia, Excoecaria agallocha, Geranium thunbergii, Geum japonicum, Haematoxylum campechianum, Juglans sigillata, Liquidambar formosana, Loropetalum chinense, Lotus corniculatus, Mangifera indica, Melaleuca leucadendra, Nymphaea lotus , Paeonia lactiflora, Paeonia suffruticosa, Phyllagathis rotundifolia, Phyllanthus emblica, Plantago major, Platycarya strobilacea, Punica granatum, Quercus acutissima, Quercus aliena, Quercus infectoria, Quercus phillyraeoides, Quercus robur, Rhodiola rosea, Rhodiola sachalinensis, Rhoiptelea chiliantha, Rhus chinensis, Rhus typhina, Rosa davurica, Sanguisorba officinalis, Syzygium aromaticum, Terminalia chebula, Toxicodendron vernicifluum and Woodfordia fruticosa. Penta-O-galloyl-beta-D-glucose was first documented in 2018 (PMID: 30110480). Based on a literature review very few articles have been published on 1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose (PMID: 34951173).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222542D          

 67 72  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.4289   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 12 18  1  0  0  0  0
  4 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
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 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 27 29  1  0  0  0  0
 26 30  1  0  0  0  0
 25 31  1  0  0  0  0
  3 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
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 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
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 39 41  1  0  0  0  0
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 37 43  1  0  0  0  0
  2 44  1  1  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 50 51  1  0  0  0  0
 51 52  2  0  0  0  0
 47 52  1  0  0  0  0
 51 53  1  0  0  0  0
 50 54  1  0  0  0  0
 49 55  1  0  0  0  0
  1 56  1  6  0  0  0
 56 57  1  0  0  0  0
 57 58  2  0  0  0  0
 57 59  1  0  0  0  0
 59 60  2  0  0  0  0
 60 61  1  0  0  0  0
 61 62  2  0  0  0  0
 62 63  1  0  0  0  0
 63 64  2  0  0  0  0
 59 64  1  0  0  0  0
 63 65  1  0  0  0  0
 62 66  1  0  0  0  0
 61 67  1  0  0  0  0
M  END

     RDKit          3D

 99104  0  0  0  0  0  0  0  0999 V2000
    3.9657   -0.0337   -3.9038 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0254   -1.1473   -3.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8504   -1.8429   -3.1587 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5721   -1.4600   -3.5525 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0904   -0.1456   -2.9827 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1810    0.1714   -3.3636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0752    0.4425   -2.3827 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4274    0.4146   -2.7544 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7382    2.5428   -2.1098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6782    1.5255   -2.9790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3255    0.4626   -3.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.2871   -0.6048   -4.4720 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.2897   -1.2429    2.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8336   -0.1689    3.0033 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.8401   -4.8177    1.8802 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3842    0.0083   -0.5616 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282222542D          

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M  END
> <DATABASE_ID>
NP0075653

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(=CC(O)=C1O)C(=O)OC[C@H]1O[C@@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C41H32O26/c42-17-1-12(2-18(43)28(17)52)36(57)62-11-27-33(64-37(58)13-3-19(44)29(53)20(45)4-13)34(65-38(59)14-5-21(46)30(54)22(47)6-14)35(66-39(60)15-7-23(48)31(55)24(49)8-15)41(63-27)67-40(61)16-9-25(50)32(56)26(51)10-16/h1-10,27,33-35,41-56H,11H2/t27-,33-,34+,35-,41+/m1/s1

> <INCHI_KEY>
QJYNZEYHSMRWBK-NIKIMHBISA-N

> <FORMULA>
C41H32O26

> <MOLECULAR_WEIGHT>
940.681

> <EXACT_MASS>
940.11818115

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_ATOM_COUNT>
99

> <JCHEM_AVERAGE_POLARIZABILITY>
84.4804169280118

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
15

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6R)-3,4,5-tris(3,4,5-trihydroxybenzoyloxy)-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
3.43

> <JCHEM_LOGP>
4.990480200333333

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.8333341961662954

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.434932913585429

> <JCHEM_PKA_STRONGEST_BASIC>
-5.548951582132848

> <JCHEM_POLAR_SURFACE_AREA>
444.18000000000006

> <JCHEM_REFRACTIVITY>
214.74690000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6R)-3,4,5-tris(3,4,5-trihydroxybenzoyloxy)-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -1.334 -16.170   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6   56                                                  
CONECT    2    1    3   44                                                  
CONECT    3    2    4   32                                                  
CONECT    4    3    5   19                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   10                                                       
CONECT   16   14                                                            
CONECT   17   13                                                            
CONECT   18   12                                                            
CONECT   19    4   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25   27   30                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27   23                                                       
CONECT   29   27                                                            
CONECT   30   26                                                            
CONECT   31   25                                                            
CONECT   32    3   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   43                                                  
CONECT   38   37   39   42                                                  
CONECT   39   38   40   41                                                  
CONECT   40   39   35                                                       
CONECT   41   39                                                            
CONECT   42   38                                                            
CONECT   43   37                                                            
CONECT   44    2   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48   52                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50   55                                                  
CONECT   50   49   51   54                                                  
CONECT   51   50   52   53                                                  
CONECT   52   51   47                                                       
CONECT   53   51                                                            
CONECT   54   50                                                            
CONECT   55   49                                                            
CONECT   56    1   57                                                       
CONECT   57   56   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   60   64                                                  
CONECT   60   59   61                                                       
CONECT   61   60   62   67                                                  
CONECT   62   61   63   66                                                  
CONECT   63   62   64   65                                                  
CONECT   64   63   59                                                       
CONECT   65   63                                                            
CONECT   66   62                                                            
CONECT   67   61                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  144    0
END

View in JSmol

Synonyms

Value	Source
1,2,3,4,6-Penta-O-galloyl-beta-D-glucopyranose	ChEBI
1,2,3,4,6-Penta-O-galloyl-beta-D-glucopyranoside	ChEBI
1,2,3,4,6-Penta-O-galloyl-beta-D-glucose	ChEBI
1,2,3,4,6-Penta-O-galloyl-beta-D-glucoside	ChEBI
1,2,3,4,6-Pentagalloyl-beta-D-glucopyranose	ChEBI
1,2,3,4,6-Pentagalloyl-beta-D-glucopyranoside	ChEBI
1,2,3,4,6-Pentagalloyl-beta-D-glucose	ChEBI
1,2,3,4,6-PGG	ChEBI
beta-1,2,3,4,6-Pentagalloylglucose	ChEBI
beta-D-Glucopyranose pentakis(3,4,5-trihydroxybenzoate)	ChEBI
Penta-O-galloyl-beta-D-glucopyranose	ChEBI
Penta-O-galloyl-beta-D-glucose	ChEBI
Pentagalloyl-beta-D-glucose	ChEBI
Pentagalloylglucose	ChEBI
1,2,3,4,6-Penta-O-galloyl-b-D-glucopyranose	Generator
1,2,3,4,6-Penta-O-galloyl-β-D-glucopyranose	Generator
1,2,3,4,6-Penta-O-galloyl-b-D-glucopyranoside	Generator
1,2,3,4,6-Penta-O-galloyl-β-D-glucopyranoside	Generator
1,2,3,4,6-Penta-O-galloyl-b-D-glucose	Generator
1,2,3,4,6-Penta-O-galloyl-β-D-glucose	Generator
1,2,3,4,6-Penta-O-galloyl-b-D-glucoside	Generator
1,2,3,4,6-Penta-O-galloyl-β-D-glucoside	Generator
1,2,3,4,6-Pentagalloyl-b-D-glucopyranose	Generator
1,2,3,4,6-Pentagalloyl-β-D-glucopyranose	Generator
1,2,3,4,6-Pentagalloyl-b-D-glucopyranoside	Generator
1,2,3,4,6-Pentagalloyl-β-D-glucopyranoside	Generator
1,2,3,4,6-Pentagalloyl-b-D-glucose	Generator
1,2,3,4,6-Pentagalloyl-β-D-glucose	Generator
b-1,2,3,4,6-Pentagalloylglucose	Generator
Β-1,2,3,4,6-pentagalloylglucose	Generator
b-D-Glucopyranose pentakis(3,4,5-trihydroxybenzoate)	Generator
b-D-Glucopyranose pentakis(3,4,5-trihydroxybenzoic acid)	Generator
beta-D-Glucopyranose pentakis(3,4,5-trihydroxybenzoic acid)	Generator
Β-D-glucopyranose pentakis(3,4,5-trihydroxybenzoate)	Generator
Β-D-glucopyranose pentakis(3,4,5-trihydroxybenzoic acid)	Generator
Penta-O-galloyl-b-D-glucopyranose	Generator
Penta-O-galloyl-β-D-glucopyranose	Generator
Penta-O-galloyl-b-D-glucose	Generator
Penta-O-galloyl-β-D-glucose	Generator
Pentagalloyl-b-D-glucose	Generator
Pentagalloyl-β-D-glucose	Generator
1,2,3,4,6-Pentakis-O-galloyl-b-D-glucose	Generator
1,2,3,4,6-Pentakis-O-galloyl-β-D-glucose	Generator
1,2,3,4,6-Penta-O-galloylglucose	MeSH
1,2,3,4,6-Pentagalloylglucose	MeSH
Penta-1,2,3,4,6-O-galloyl-beta-D-glucose	MeSH
Penta-O-galloyl-alpha-D-glucopyranose	MeSH
beta-Penta-O-galloyl-glucose	MeSH
beta-Penta-O-galloyl-glucose, (D)-isomer	MeSH
Penta-O-galloyl-alpha-D-glucose	MeSH
Penta-O-galloyl-beta-D-glucoside	MeSH
1,2,3,4,6-Penta-O-galloyl beta-glucopyranose	MeSH

Chemical Formula

C₄₁H₃₂O₂₆

Average Mass

940.6810 Da

Monoisotopic Mass

940.11818 Da

IUPAC Name

(2S,3R,4S,5R,6R)-3,4,5-tris(3,4,5-trihydroxybenzoyloxy)-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl 3,4,5-trihydroxybenzoate

Traditional Name

(2S,3R,4S,5R,6R)-3,4,5-tris(3,4,5-trihydroxybenzoyloxy)-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-2-yl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

OC1=CC(=CC(O)=C1O)C(=O)OC[C@H]1O[C@@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C41H32O26/c42-17-1-12(2-18(43)28(17)52)36(57)62-11-27-33(64-37(58)13-3-19(44)29(53)20(45)4-13)34(65-38(59)14-5-21(46)30(54)22(47)6-14)35(66-39(60)15-7-23(48)31(55)24(49)8-15)41(63-27)67-40(61)16-9-25(50)32(56)26(51)10-16/h1-10,27,33-35,41-56H,11H2/t27-,33-,34+,35-,41+/m1/s1

InChI Key

QJYNZEYHSMRWBK-NIKIMHBISA-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
Acer truncatum	LOTUS Database	35616633
Agrobacterium rhizogenes	LOTUS Database	35616633
Caryocar villosum	LOTUS Database	35616633
Castanopsis fissa	LOTUS Database	35616633
Cercidiphyllum japonicum	LOTUS Database	35616633
Cornulaca monacantha	Plant	KNApSAcK
Cotinus coggygria	LOTUS Database	35616633
Cuphea hyssopifolia	LOTUS Database	35616633
Eucalyptus alba	LOTUS Database	35616633
Eucalyptus globulus	LOTUS Database	35616633
Euphorbia helioscopia	LOTUS Database	35616633
Euphorbia humifusa	LOTUS Database	35616633
Euphorbia jolkini	LOTUS Database	35616633
Euphorbia maculata	LOTUS Database	35616633
Euphorbia thymifolia	LOTUS Database	35616633
Excoecaria agallocha	LOTUS Database	35616633
Geranium thunbergii	LOTUS Database	35616633
Geum japonicum	LOTUS Database	35616633
Haematoxylum campechianum	LOTUS Database	35616633
Juglans sigillata	LOTUS Database	35616633
Liquidambar formosana	LOTUS Database	35616633
Loropetalum chinense	LOTUS Database	35616633
Lotus corniculatus	LOTUS Database	35616633
Mangifera indica	LOTUS Database	35616633
Melaleuca leucadendra	LOTUS Database	35616633
Nymphaea lotus	Plant	KNApSAcK
Paeonia lactiflora	LOTUS Database	35616633
Paeonia suffruticosa	LOTUS Database	35616633
Phyllagathis rotundifolia	LOTUS Database	35616633
Phyllanthus emblica	LOTUS Database	35616633
Plantago major	LOTUS Database	35616633
Platycarya strobilacea	LOTUS Database	35616633
Punica granatum	LOTUS Database	35616633
Quercus acutissima	LOTUS Database	35616633
Quercus aliena	LOTUS Database	35616633
Quercus infectoria	LOTUS Database	35616633
Quercus phillyraeoides	LOTUS Database	35616633
Quercus robur	LOTUS Database	35616633
Rhodiola rosea	LOTUS Database	35616633
Rhodiola sachalinensis	LOTUS Database	35616633
Rhoiptelea chiliantha	LOTUS Database	35616633
Rhus chinensis	LOTUS Database	35616633
Rhus typhina	LOTUS Database	35616633
Rosa davurica	LOTUS Database	35616633
Sanguisorba officinalis	LOTUS Database	35616633
Syzygium aromaticum	LOTUS Database	35616633
Terminalia chebula	LOTUS Database	35616633
Toxicodendron vernicifluum	LOTUS Database	35616633
Woodfordia fruticosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tannins. These are naturally occurring polyphenols which be categorized into four main classes: Hydrolyzable tannin (based on ellagic acid or gallic acid), condensed tannins (made of oligomeric or polymeric proanthocyanidins), complex tannins (made of a catechin bound to a gallotannin or elagitannin), and phlorotannins (oligomers of phloroglucinol).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Not Available

Direct Parent

Tannins

Alternative Parents

Substituents

Tannin
Pentacarboxylic acid or derivatives
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Pyrogallol derivative
Benzenetriol
Benzoic acid or derivatives
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Oxane
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

gallate ester (CHEBI:18082 )
galloyl beta-D-glucose (CHEBI:18082 )
Ellagitannins (C04576 )

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	3.43	ALOGPS
logP	4.99	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.43	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	15	ChemAxon
Polar Surface Area	444.18 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	214.75 m³·mol⁻¹	ChemAxon
Polarizability	84.48 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002933

Chemspider ID

58735

KEGG Compound ID

C04576

BioCyc ID

12346-PENTAKIS-O-GALLOYL-BETA-D-GLUC

BiGG ID

Not Available

Wikipedia Link

1,2,3,4,6-Pentagalloyl glucose

METLIN ID

Not Available

PubChem Compound

65238

PDB ID

Not Available

ChEBI ID

18082

Good Scents ID

rw1736911

References

General References

Zhao QL, Yang PW, Qian DW, Bian XK, Wang YF, Zhu ZH, Guo S, Wang TJ, Yan H, Duan JA: [Effects and evaluation of different processing and drying methods on components in Paeoniae Radix Alba]. Zhongguo Zhong Yao Za Zhi. 2021 Nov;46(22):5839-5847. doi: 10.19540/j.cnki.cjcmm.20210319.303. [PubMed:34951173 ]
Yang L, Yin P, Ho CT, Yu M, Sun L, Liu Y: Effects of thermal treatments on 10 major phenolics and their antioxidant contributions in Acer truncatum leaves and flowers. R Soc Open Sci. 2018 Jun 27;5(6):180364. doi: 10.1098/rsos.180364. eCollection 2018 Jun. [PubMed:30110480 ]

Showing NP-Card for Penta-O-galloyl-beta-D-glucose (NP0075653)

MOL for NP0075653 (Penta-O-galloyl-beta-D-glucose)

3D MOL for NP0075653 (Penta-O-galloyl-beta-D-glucose)

3D SDF for NP0075653 (Penta-O-galloyl-beta-D-glucose)

3D-SDF for NP0075653 (Penta-O-galloyl-beta-D-glucose)

PDB for NP0075653 (Penta-O-galloyl-beta-D-glucose)

3D PDB for NP0075653 (Penta-O-galloyl-beta-D-glucose)

SMILES for NP0075653 (Penta-O-galloyl-beta-D-glucose)

INCHI for NP0075653 (Penta-O-galloyl-beta-D-glucose)

Structure for NP0075653 (Penta-O-galloyl-beta-D-glucose)

3D Structure for NP0075653 (Penta-O-galloyl-beta-D-glucose)