NP-MRD: Showing NP-Card for (10r,11s,12r,13s,15r)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-12,13-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2(7),3,5,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate (NP0187828)

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Record Information

Version

2.0

Created at

2022-09-04 04:03:54 UTC

Updated at

2022-09-04 04:03:55 UTC

NP-MRD ID

NP0187828

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(10r,11s,12r,13s,15r)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-12,13-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2(7),3,5,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate

Description

Eugeniin, also known as tellimagrandin II or cornustannin 2, belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Eugeniin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (10r,11s,12r,13s,15r)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-12,13-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2(7),3,5,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate is found in Betula pubescens, Camellia oleifera, Camptotheca acuminata, Castanopsis fissa, Combretum indicum, Coriaria japonica, Cornus controversa, Cornus officinalis, Corylus heterophylla, Cuphea hyssopifolia, Eucalyptus globulus, Eucalyptus nitens, Eucalyptus viminalis, Euphorbia prostrata, Euphorbia thymifolia, Euphorbia tirucalli, Filipendula camtschatica, Geum japonicum, Juglans regia, Liquidambar formosana, Loropetalum chinense, Mallotus repandus, Melaleuca leucadendra, Myriophyllum aquaticum, Myriophyllum spicatum, Paeonia lactiflora, Paeonia obovata, Platycarya strobilacea, Quercus acutissima, Quercus aliena, Quercus coccifera, Quercus phillyraeoides, Quercus robur, Quercus suber, Rosa gallica, Rosa roxburghii, Rosa rugosa, Sanguisorba officinalis, Schima wallichii, Syzygium aqueum, Syzygium aromaticum, Tamarix nilotica, Tamarix parviflora, Tellima grandiflora and Trapa bicornis. (10r,11s,12r,13s,15r)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-12,13-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2(7),3,5,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate was first documented in 2016 (PMID: 27272505). Based on a literature review a small amount of articles have been published on eugeniin (PMID: 35851119) (PMID: 33590040) (PMID: 28049912).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042206032D          

 67 73  0  0  1  0            999 V2000
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  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
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 32 31  1  1  0  0  0
  6 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
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  4 46  1  0  0  0  0
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  2 59  1  0  0  0  0
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 59 67  1  0  0  0  0
M  END

     RDKit          3D

 97103  0  0  0  0  0  0  0  0999 V2000
    1.4230   -4.8062    0.4161 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3765   -4.6027   -0.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5531   -3.5678   -1.2367 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309042206032D          

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M  END
> <DATABASE_ID>
NP0187828

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(=CC(O)=C1O)C(=O)O[C@@H]1O[C@@H]2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(C=C(O)C(O)=C3O)C(=O)O[C@H]2[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/C41H30O26/c42-15-1-10(2-16(43)26(15)50)36(57)65-34-33-23(9-62-39(60)13-7-21(48)29(53)31(55)24(13)25-14(40(61)64-33)8-22(49)30(54)32(25)56)63-41(67-38(59)12-5-19(46)28(52)20(47)6-12)35(34)66-37(58)11-3-17(44)27(51)18(45)4-11/h1-8,23,33-35,41-56H,9H2/t23-,33-,34+,35-,41+/m1/s1

> <INCHI_KEY>
JCGHAEBIBSEQAD-UUUCSUBKSA-N

> <FORMULA>
C41H30O26

> <MOLECULAR_WEIGHT>
938.665

> <EXACT_MASS>
938.102531086

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_ATOM_COUNT>
97

> <JCHEM_AVERAGE_POLARIZABILITY>
84.0003393822009

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
15

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(10R,11S,12R,13S,15R)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-12,13-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0^{2,7}.0^{10,15}]tricosa-1(23),2(7),3,5,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate

> <JCHEM_LOGP>
4.264459746333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.713248382916182

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.29176606489496

> <JCHEM_PKA_STRONGEST_BASIC>
-6.0536959167869435

> <JCHEM_POLAR_SURFACE_AREA>
444.1800000000001

> <JCHEM_REFRACTIVITY>
213.8251

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(10R,11S,12R,13S,15R)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-12,13-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0^{2,7}.0^{10,15}]tricosa-1(23),2(7),3,5,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0       0.207   1.172   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.223   0.600   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.442  -0.925   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.232  -1.877   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.198  -1.304   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.409  -2.256   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.417  -1.092   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.895  -0.658   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.372  -1.092   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.205   0.203   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.381  -2.256   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.591  -1.304   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.021  -1.877   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.232  -0.925   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.240  -3.401   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.670  -3.973   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.030  -4.353   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.249  -5.877   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.600  -3.781   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.960  -5.181   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.665  -6.014   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.738  -7.552   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.107  -8.258   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.180  -9.796   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.402  -7.425   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.771  -8.131   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.329  -5.887   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.764  -6.446   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.125  -6.014   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.691  -7.492   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       2.829  -5.181   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.189  -3.781   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.760  -4.353   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.541  -5.877   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -0.889  -6.450   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.100  -5.498   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.108  -7.974   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.102  -8.926   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.117 -10.450   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       1.094 -11.402   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -1.547 -11.023   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -1.766 -12.547   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -2.757 -10.071   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -4.187 -10.643   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -2.538  -8.546   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -0.451  -3.401   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -1.880  -3.973   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -3.091  -3.021   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -2.872  -1.497   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -4.521  -3.594   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -4.740  -5.118   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -6.169  -5.690   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      -6.389  -7.215   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      -7.380  -4.738   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      -8.810  -5.311   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      -7.161  -3.214   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      -8.371  -2.262   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      -5.731  -2.642   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      -2.433   1.552   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      -3.863   0.979   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      -5.074   1.931   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      -6.503   1.359   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0      -4.854   3.456   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0      -6.065   4.408   0.000  0.00  0.00           O+0
HETATM   65  C   UNK     0      -3.425   4.028   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0      -3.206   5.552   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0      -2.214   3.076   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   59                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   46                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   32                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   11   20                                                  
CONECT   20   19   21   27                                                  
CONECT   21   20   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   20   28                                                  
CONECT   28   27                                                            
CONECT   29   21   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31    6   33                                                  
CONECT   33   32   34   46                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   45                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   37                                                       
CONECT   46   33    4   47                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51   58                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   50                                                       
CONECT   59    2   60   67                                                  
CONECT   60   59   61                                                       
CONECT   61   60   62   63                                                  
CONECT   62   61                                                            
CONECT   63   61   64   65                                                  
CONECT   64   63                                                            
CONECT   65   63   66   67                                                  
CONECT   66   65                                                            
CONECT   67   65   59                                                       
MASTER        0    0    0    0    0    0    0    0   67    0  146    0
END

View in JSmol

Synonyms

Value	Source
1,2,3-Trigalloyl-4,6-hexahydroxydiphenoyl beta-D-glucopyranose	ChEBI
beta-D-Glucopyranose,cyclic4,6-(4,4',5,5',6,6'-hexahydroxy(1,1'-biphenyl)-2,2'-dicarboxylate)1,2,3-tris(3,4,5-trihydroxybenzoate)	ChEBI
Cornustannin 2	ChEBI
Tellimagrandin II	ChEBI
1,2,3-Trigalloyl-4,6-hexahydroxydiphenoyl b-D-glucopyranose	Generator
1,2,3-Trigalloyl-4,6-hexahydroxydiphenoyl β-D-glucopyranose	Generator
b-D-Glucopyranose,cyclic4,6-(4,4',5,5',6,6'-hexahydroxy(1,1'-biphenyl)-2,2'-dicarboxylate)1,2,3-tris(3,4,5-trihydroxybenzoate)	Generator
b-D-Glucopyranose,cyclic4,6-(4,4',5,5',6,6'-hexahydroxy(1,1'-biphenyl)-2,2'-dicarboxylic acid)1,2,3-tris(3,4,5-trihydroxybenzoic acid)	Generator
beta-D-Glucopyranose,cyclic4,6-(4,4',5,5',6,6'-hexahydroxy(1,1'-biphenyl)-2,2'-dicarboxylic acid)1,2,3-tris(3,4,5-trihydroxybenzoic acid)	Generator
Β-D-glucopyranose,cyclic4,6-(4,4',5,5',6,6'-hexahydroxy(1,1'-biphenyl)-2,2'-dicarboxylate)1,2,3-tris(3,4,5-trihydroxybenzoate)	Generator
Β-D-glucopyranose,cyclic4,6-(4,4',5,5',6,6'-hexahydroxy(1,1'-biphenyl)-2,2'-dicarboxylic acid)1,2,3-tris(3,4,5-trihydroxybenzoic acid)	Generator

Chemical Formula

C₄₁H₃₀O₂₆

Average Mass

938.6650 Da

Monoisotopic Mass

938.10253 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC1=CC(=CC(O)=C1O)C(=O)O[C@@H]1O[C@@H]2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(C=C(O)C(O)=C3O)C(=O)O[C@H]2[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/C41H30O26/c42-15-1-10(2-16(43)26(15)50)36(57)65-34-33-23(9-62-39(60)13-7-21(48)29(53)31(55)24(13)25-14(40(61)64-33)8-22(49)30(54)32(25)56)63-41(67-38(59)12-5-19(46)28(52)20(47)6-12)35(34)66-37(58)11-3-17(44)27(51)18(45)4-11/h1-8,23,33-35,41-56H,9H2/t23-,33-,34+,35-,41+/m1/s1

InChI Key

JCGHAEBIBSEQAD-UUUCSUBKSA-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
Betula pubescens	LOTUS Database	35616633
Camellia oleifera	LOTUS Database	35616633
Camptotheca acuminata	LOTUS Database	35616633
Castanopsis fissa	LOTUS Database	35616633
Combretum indicum	LOTUS Database	35616633
Coriaria japonica	LOTUS Database	35616633
Cornus controversa	LOTUS Database	35616633
Cornus officinalis	LOTUS Database	35616633
Corylus heterophylla	LOTUS Database	35616633
Cuphea hyssopifolia	LOTUS Database	35616633
Eucalyptus globulus	LOTUS Database	35616633
Eucalyptus nitens	LOTUS Database	35616633
Eucalyptus viminalis	LOTUS Database	35616633
Euphorbia prostrata	LOTUS Database	35616633
Euphorbia thymifolia	LOTUS Database	35616633
Euphorbia tirucalli	LOTUS Database	35616633
Filipendula camtschatica	LOTUS Database	35616633
Geum japonicum	LOTUS Database	35616633
Juglans regia	LOTUS Database	35616633
Liquidambar formosana	LOTUS Database	35616633
Loropetalum chinense	LOTUS Database	35616633
Mallotus repandus	LOTUS Database	35616633
Melaleuca leucadendra	LOTUS Database	35616633
Myriophyllum aquaticum	LOTUS Database	35616633
Myriophyllum spicatum	LOTUS Database	35616633
Paeonia lactiflora	LOTUS Database	35616633
Paeonia obovata	LOTUS Database	35616633
Platycarya strobilacea	LOTUS Database	35616633
Quercus acutissima	LOTUS Database	35616633
Quercus aliena	LOTUS Database	35616633
Quercus coccifera	LOTUS Database	35616633
Quercus phillyraeoides	LOTUS Database	35616633
Quercus robur	LOTUS Database	35616633
Quercus suber	LOTUS Database	35616633
Rosa gallica	LOTUS Database	35616633
Rosa roxburghii	LOTUS Database	35616633
Rosa rugosa	LOTUS Database	35616633
Sanguisorba officinalis	LOTUS Database	35616633
Schima wallichii	LOTUS Database	35616633
Syzygium aqueum	LOTUS Database	35616633
Syzygium aromaticum	LOTUS Database	35616633
Tamarix nilotica	LOTUS Database	35616633
Tamarix parviflora	LOTUS Database	35616633
Tellima grandiflora	LOTUS Database	35616633
Trapa bicornis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable 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
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
Lactone
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:4916 )
gallate ester (CHEBI:4916 )
lactone (CHEBI:4916 )
ellagitannin (CHEBI:4916 )
Ellagitannins (C10224 )

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	4.26	ChemAxon
pKa (Strongest Acidic)	7.29	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002920

Chemspider ID

391036

KEGG Compound ID

C10224

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tellimagrandin_II

METLIN ID

Not Available

PubChem Compound

442679

PDB ID

Not Available

ChEBI ID

4916

Good Scents ID

Not Available

References

General References

Yu YH, Jia L, Zeng HT, Yuan T: [Hydrolyzable tannins from flowers of Punica granatum and their anti-diabetic activities]. Zhongguo Zhong Yao Za Zhi. 2022 Jun;47(12):3258-3264. doi: 10.19540/j.cnki.cjcmm.20220129.201. [PubMed:35851119 ]
Yasuda M, Ikeoka M, Kondo SI: Skin-related enzyme inhibitory activity by hydrolyzable polyphenols in water chestnut (Trapa natans) husk. Biosci Biotechnol Biochem. 2021 Feb 24;85(3):666-674. doi: 10.1093/bbb/zbaa076. [PubMed:33590040 ]
Takeuchi H, Ueda Y, Furuta T, Kawabata T: Total Synthesis of Ellagitannins via Sequential Site-Selective Functionalization of Unprotected D-Glucose. Chem Pharm Bull (Tokyo). 2017;65(1):25-32. doi: 10.1248/cpb.c16-00436. [PubMed:28049912 ]
Shimamura Y, Aoki N, Sugiyama Y, Tanaka T, Murata M, Masuda S: Plant-Derived Polyphenols Interact with Staphylococcal Enterotoxin A and Inhibit Toxin Activity. PLoS One. 2016 Jun 7;11(6):e0157082. doi: 10.1371/journal.pone.0157082. eCollection 2016. [PubMed:27272505 ]
LOTUS database [Link]

Showing NP-Card for (10r,11s,12r,13s,15r)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-12,13-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2(7),3,5,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate (NP0187828)

MOL for NP0187828 ((10r,11s,12r,13s,15r)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-12,13-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2(7),3,5,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate)

3D MOL for NP0187828 ((10r,11s,12r,13s,15r)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-12,13-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2(7),3,5,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate)

3D SDF for NP0187828 ((10r,11s,12r,13s,15r)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-12,13-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2(7),3,5,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate)

3D-SDF for NP0187828 ((10r,11s,12r,13s,15r)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-12,13-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2(7),3,5,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate)

PDB for NP0187828 ((10r,11s,12r,13s,15r)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-12,13-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2(7),3,5,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate)

3D PDB for NP0187828 ((10r,11s,12r,13s,15r)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-12,13-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2(7),3,5,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate)

SMILES for NP0187828 ((10r,11s,12r,13s,15r)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-12,13-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2(7),3,5,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate)

INCHI for NP0187828 ((10r,11s,12r,13s,15r)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-12,13-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2(7),3,5,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate)

Structure for NP0187828 ((10r,11s,12r,13s,15r)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-12,13-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2(7),3,5,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate)

3D Structure for NP0187828 ((10r,11s,12r,13s,15r)-3,4,5,21,22,23-hexahydroxy-8,18-dioxo-12,13-bis(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2(7),3,5,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate)