NP-MRD: Showing NP-Card for 7,8,9,12,13,14,25,26,27,30,31,32,35,36,37,46-hexadecahydroxy-3,18,21,41,43-pentaoxanonacyclo[27.13.3.1³⁸,⁴².0²,²⁰.0⁵,¹⁰.0¹¹,¹⁶.0²³,²⁸.0³³,⁴⁵.0³⁴,³⁹]hexatetraconta-5,7,9,11(16),12,14,23,25,27,29,31,33(45),34(39),35,37-pentadecaene-4,17,22,40,44-pentone (NP0183044)

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Record Information

Version

2.0

Created at

2022-09-03 21:53:04 UTC

Updated at

2022-09-03 21:53:04 UTC

NP-MRD ID

NP0183044

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,8,9,12,13,14,25,26,27,30,31,32,35,36,37,46-hexadecahydroxy-3,18,21,41,43-pentaoxanonacyclo[27.13.3.1³⁸,⁴².0²,²⁰.0⁵,¹⁰.0¹¹,¹⁶.0²³,²⁸.0³³,⁴⁵.0³⁴,³⁹]hexatetraconta-5,7,9,11(16),12,14,23,25,27,29,31,33(45),34(39),35,37-pentadecaene-4,17,22,40,44-pentone

Description

Vescalagin, also known as vescalene or castalagin, 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. Castalagin thus forms from a pentagalloyl-glucose structure. After conversion of casuarictin to pedunculagin, the pyranose ring of the glucose opens and the family of compounds including casuariin, casuarinin, castalagin, and castlin, vescalagin and vescalin forms. Vescalagin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, vescalagin has been detected, but not quantified in, a few different foods, such as european chestnuts, nuts, and pomegranates. This could make vescalagin a potential biomarker for the consumption of these foods. Vescalagin is one of the most abundant ellagitannins extracted from oak wood using white wine. Castalagin is an ellagitannin, a type of hydrolyzable tannin, found in oak and chestnut wood and in the stem barks of Anogeissus leiocarpus and Terminalia avicennoides. During aging of alcohols in oak barrels, vescalagin can be extracted from the wood and can subsequently be transformed into new derivatives by chemical reactions. In some plants including oak and chestnut, the ellagitannins are formed from 1,2,3,4,6-pentagalloyl-glucose and further elaborated via oxidative dehydrogenation (tellimagrandin II and casuarictin formations). Castalagin and vescalagin (1,2,3,5-nonahydroxytriphenoyl-4,6-hexahydroxydiphenoyl-glucoses) can be further polymerized in their corresponding dimers roburin A and roburin D, and 33-carboxy-33-deoxyvescalagin. Castalagin is the (33beta)-isomer of vescalagin. Grandinin is a castalagin glycoside by binding of the pentose lyxose. 7,8,9,12,13,14,25,26,27,30,31,32,35,36,37,46-hexadecahydroxy-3,18,21,41,43-pentaoxanonacyclo[27.13.3.1³⁸,⁴².0²,²⁰.0⁵,¹⁰.0¹¹,¹⁶.0²³,²⁸.0³³,⁴⁵.0³⁴,³⁹]hexatetraconta-5,7,9,11(16),12,14,23,25,27,29,31,33(45),34(39),35,37-pentadecaene-4,17,22,40,44-pentone is found in Bredia tuberculata, Castanea crenata, Castanea sativa, Chrysolepis sempervirens, Combretum indicum, Hippophae rhamnoides, Lagerstroemia speciosa, Lumnitzera racemosa, Lythrum salicaria, Melaleuca leucadendra, Melastoma candidum, Morella esculenta, Psidium guajava, Quercus alba, Quercus lusitanica, Quercus mongolica, Quercus petraea, Quercus phillyraeoides, Quercus robur, Quercus salicina, Quercus suber, Siphoneugena densiflora, Syzygium aqueum, Syzygium grande, Terminalia catappa, Thiloa glaucocarpa and Pleroma semidecandrum. The flavono-ellagitannin known as acutissimin A is created when the oak tannin vescalagin interacts with a flavonoid in wine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241217182D          

 67 75  0  0  0  0            999 V2000
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   -0.8618   -4.6378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6826   -5.1299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2 66  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4 59  1  0  0  0  0
  5  6  1  0  0  0  0
  5 53  1  0  0  0  0
  6  7  1  0  0  0  0
  6 66  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  2  0  0  0  0
 10 11  1  0  0  0  0
 10 16  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
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 27 28  1  0  0  0  0
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 66 67  1  0  0  0  0
M  END

     RDKit          3D

 93101  0  0  0  0  0  0  0  0999 V2000
    4.6935    2.1387    1.5178 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6654    1.3580    1.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9986    1.1298    2.6648 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7415    1.6286    3.0643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6500    1.0450    2.1489 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5142    1.7109    2.4064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0018    2.9738    2.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4465    3.6990    2.9556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0744    3.5983    0.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0946    4.6465    0.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2636    5.2674   -0.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3438    4.8683   -1.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8583    3.4642   -2.8559 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8943    2.2935   -0.6558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7547    2.6517   -1.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.5023    2.1626   -3.3110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7927    0.5011   -1.7726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7124   -0.3496   -2.3624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9972    0.1506   -0.7502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0086    1.0240   -0.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4968    0.5804    1.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1422    0.9552    2.3603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4464   -0.1641    1.2902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6180   -1.1241    1.8210 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5464   -0.4565    2.5580 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7329   -0.9688    2.4884 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5252    1.6395   -2.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4971   -1.7466   -0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8517   -1.3001   -0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8963   -1.9617    0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2171   -1.6220    0.1925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6618   -3.1497    0.9611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7055   -3.8541    1.5186 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02241217182D          

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M  END
> <DATABASE_ID>
NP0183044

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C2OC(=O)C3=C(C(O)=C(O)C(O)=C13)C1=C3C(=C(O)C(O)=C1O)C1=C(C=C(O)C(O)=C1O)C(=O)OC1COC(=O)C4=C(C(O)=C(O)C(O)=C4)C4=C(C=C(O)C(O)=C4O)C(=O)OC1C2OC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C41H26O26/c42-8-1-5-12(24(48)21(8)45)13-6(2-9(43)22(46)25(13)49)39(60)65-34-11(4-63-37(5)58)64-38(59)7-3-10(44)23(47)26(50)14(7)15-18-16(28(52)32(56)27(15)51)17-19-20(30(54)33(57)29(17)53)31(55)35(66-41(19)62)36(34)67-40(18)61/h1-3,11,31,34-36,42-57H,4H2

> <INCHI_KEY>
UDYKDZHZAKSYCO-UHFFFAOYSA-N

> <FORMULA>
C41H26O26

> <MOLECULAR_WEIGHT>
934.6295

> <EXACT_MASS>
934.071231004

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
81.95412395344825

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
16

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7,8,9,12,13,14,25,26,27,30,31,32,35,36,37,46-hexadecahydroxy-3,18,21,41,43-pentaoxanonacyclo[27.13.3.1³⁸,⁴².0²,²⁰.0⁵,¹⁰.0¹¹,¹⁶.0²³,²⁸.0³³,⁴⁵.0³⁴,³⁹]hexatetraconta-5(10),6,8,11(16),12,14,23(28),24,26,29,31,33(45),34(39),35,37-pentadecaene-4,17,22,40,44-pentone

> <ALOGPS_LOGP>
2.74

> <JCHEM_LOGP>
2.0259335789999997

> <ALOGPS_LOGS>
-2.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.563872995015127

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.139480581657935

> <JCHEM_PKA_STRONGEST_BASIC>
-6.177204321276062

> <JCHEM_POLAR_SURFACE_AREA>
455.1800000000001

> <JCHEM_REFRACTIVITY>
212.68650000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.79e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,8,9,12,13,14,25,26,27,30,31,32,35,36,37,46-hexadecahydroxy-3,18,21,41,43-pentaoxanonacyclo[27.13.3.1³⁸,⁴².0²,²⁰.0⁵,¹⁰.0¹¹,¹⁶.0²³,²⁸.0³³,⁴⁵.0³⁴,³⁹]hexatetraconta-5(10),6,8,11(16),12,14,23(28),24,26,29,31,33(45),34(39),35,37-pentadecaene-4,17,22,40,44-pentone

> <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  O   UNK     0      -5.898  -8.351   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.673  -7.431   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.673  -5.899   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.600  -4.826   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.068  -5.439   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.068  -6.971   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.609  -8.657   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       7.278   6.204   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.898   5.439   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.898   3.907   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.430   3.447   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.826   7.737   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.520   6.357   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.294   5.285   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.906   3.907   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.826   3.140   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.374   3.753   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.988   2.680   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.914   2.221   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.221   0.995   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.448   0.384   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.060  -1.608   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.761   8.503   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.302   7.124   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.149   5.439   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.681   5.132   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.753   4.060   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.439   4.519   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.898   5.899   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -7.430   6.204   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -0.078   2.221   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.689   0.841   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.535  -0.076   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.535  -1.608   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.689  -2.375   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.068  -1.762   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -0.995   3.753   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       0.536   3.600   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.382   5.132   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.761   5.899   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.456   7.431   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       2.528   8.503   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       0.076   7.891   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -0.078   9.576   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      -3.753   8.656   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -3.294   6.664   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -4.826   7.124   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -5.285   8.503   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       3.906  -6.206   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       2.528  -5.899   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       2.068  -4.367   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       0.536  -4.060   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -0.689  -4.979   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -0.078  -6.511   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       1.456  -6.971   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       1.914  -8.351   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      -0.078  -8.044   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      -5.898  -3.754   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      -4.366  -3.447   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      -4.059  -1.915   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0      -2.834  -1.149   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      -2.221   0.230   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      -2.527   1.761   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      -3.906   2.527   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      -5.285   1.761   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      -3.294  -7.891   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      -3.141  -9.576   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   66                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   59                                                  
CONECT    5    4    6   53                                                  
CONECT    6    5    7   66                                                  
CONECT    7    6                                                            
CONECT    8    9                                                            
CONECT    9    8   10   13                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10                                                            
CONECT   12   13                                                            
CONECT   13    9   12   14                                                  
CONECT   14   13   15   40                                                  
CONECT   15   14   16   18                                                  
CONECT   16   10   15   21                                                  
CONECT   17   18                                                            
CONECT   18   15   17   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   32                                                  
CONECT   21   16   20   22                                                  
CONECT   22   21                                                            
CONECT   23   24                                                            
CONECT   24   23   25   43                                                  
CONECT   25   24   26   39                                                  
CONECT   26   25   27   46                                                  
CONECT   27   26   28   64                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   47                                                  
CONECT   30   29                                                            
CONECT   31   32   38                                                       
CONECT   32   20   31   33                                                  
CONECT   33   32   34   62                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   52                                                  
CONECT   36   35                                                            
CONECT   37   38                                                            
CONECT   38   31   37   39                                                  
CONECT   39   25   38   40                                                  
CONECT   40   14   39   41                                                  
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   24   41   44                                                  
CONECT   44   43                                                            
CONECT   45   46                                                            
CONECT   46   26   45   47                                                  
CONECT   47   29   46   48                                                  
CONECT   48   47                                                            
CONECT   49   50                                                            
CONECT   50   49   51   55                                                  
CONECT   51   50   52                                                       
CONECT   52   35   51   53                                                  
CONECT   53    5   52   54                                                  
CONECT   54   53   55   57                                                  
CONECT   55   50   54   56                                                  
CONECT   56   55                                                            
CONECT   57   54                                                            
CONECT   58   59                                                            
CONECT   59    4   58   60                                                  
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   33   61   63                                                  
CONECT   63   62   64                                                       
CONECT   64   27   63   65                                                  
CONECT   65   64                                                            
CONECT   66    2    6   67                                                  
CONECT   67   66                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  150    0
END

View in JSmol

Synonyms

Value	Source
Vescalagin, (33beta)-isomer	HMDB
Vescalene	HMDB
Castalagin	HMDB
Vescalin	HMDB
Vescalagin	MeSH

Chemical Formula

C₄₁H₂₆O₂₆

Average Mass

934.6295 Da

Monoisotopic Mass

934.07123 Da

IUPAC Name

7,8,9,12,13,14,25,26,27,30,31,32,35,36,37,46-hexadecahydroxy-3,18,21,41,43-pentaoxanonacyclo[27.13.3.1³⁸,⁴².0²,²⁰.0⁵,¹⁰.0¹¹,¹⁶.0²³,²⁸.0³³,⁴⁵.0³⁴,³⁹]hexatetraconta-5(10),6,8,11(16),12,14,23(28),24,26,29,31,33(45),34(39),35,37-pentadecaene-4,17,22,40,44-pentone

Traditional Name

7,8,9,12,13,14,25,26,27,30,31,32,35,36,37,46-hexadecahydroxy-3,18,21,41,43-pentaoxanonacyclo[27.13.3.1³⁸,⁴².0²,²⁰.0⁵,¹⁰.0¹¹,¹⁶.0²³,²⁸.0³³,⁴⁵.0³⁴,³⁹]hexatetraconta-5(10),6,8,11(16),12,14,23(28),24,26,29,31,33(45),34(39),35,37-pentadecaene-4,17,22,40,44-pentone

CAS Registry Number

Not Available

SMILES

OC1C2OC(=O)C3=C(C(O)=C(O)C(O)=C13)C1=C3C(=C(O)C(O)=C1O)C1=C(C=C(O)C(O)=C1O)C(=O)OC1COC(=O)C4=C(C(O)=C(O)C(O)=C4)C4=C(C=C(O)C(O)=C4O)C(=O)OC1C2OC3=O

InChI Identifier

InChI=1S/C41H26O26/c42-8-1-5-12(24(48)21(8)45)13-6(2-9(43)22(46)25(13)49)39(60)65-34-11(4-63-37(5)58)64-38(59)7-3-10(44)23(47)26(50)14(7)15-18-16(28(52)32(56)27(15)51)17-19-20(30(54)33(57)29(17)53)31(55)35(66-41(19)62)36(34)67-40(18)61/h1-3,11,31,34-36,42-57H,4H2

InChI Key

UDYKDZHZAKSYCO-UHFFFAOYSA-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
Bredia tuberculata	LOTUS Database	35616633
Castanea crenata	LOTUS Database	35616633
Castanea sativa	LOTUS Database	35616633
Chrysolepis sempervirens	LOTUS Database	35616633
Combretum indicum	LOTUS Database	35616633
Hippophae rhamnoides	LOTUS Database	35616633
Lagerstroemia speciosa	LOTUS Database	35616633
Lumnitzera racemosa	LOTUS Database	35616633
Lythrum salicaria	LOTUS Database	35616633
Melaleuca leucadendra	LOTUS Database	35616633
Melastoma candidum	LOTUS Database	35616633
Morella esculenta	LOTUS Database	35616633
Psidium guajava	LOTUS Database	35616633
Quercus alba	LOTUS Database	35616633
Quercus lusitanica	LOTUS Database	35616633
Quercus mongolica	LOTUS Database	35616633
Quercus petraea	LOTUS Database	35616633
Quercus phillyraeoides	LOTUS Database	35616633
Quercus robur	LOTUS Database	35616633
Quercus salicina	LOTUS Database	35616633
Quercus suber	LOTUS Database	35616633
Siphoneugena densiflora	LOTUS Database	35616633
Syzygium aqueum	LOTUS Database	35616633
Syzygium grande	LOTUS Database	35616633
Terminalia catappa	LOTUS Database	35616633
Thiloa glaucocarpa	LOTUS Database	35616633
Tibouchina semidecandra	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
Gallic acid or derivatives
Benzopyran
Isochromane
2-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	2.03	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	7.14	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	16	ChemAxon
Polar Surface Area	455.18 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	212.69 m³·mol⁻¹	ChemAxon
Polarizability	81.95 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon