NP-MRD: Showing NP-Card for (2s,3r,4r,5r,6r)-3,4,5-tris[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-6-{[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]methyl}oxan-2-yl 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate (NP0327909)

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Record Information

Version

1.0

Created at

2022-09-12 10:54:42 UTC

Updated at

2022-09-12 10:54:42 UTC

NP-MRD ID

NP0327909

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4r,5r,6r)-3,4,5-tris[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-6-{[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]methyl}oxan-2-yl 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate

Description

2,3-Dihydroxy-5-({[(2R,3R,4R,5R,6S)-3,4,5,6-tetrakis[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]oxan-2-yl]methoxy}carbonyl)phenyl 3,4,5-trihydroxybenzoate 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. (2s,3r,4r,5r,6r)-3,4,5-tris[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-6-{[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]methyl}oxan-2-yl 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate is found in Achillea millefolium and Camellia sinensis. Based on a literature review very few articles have been published on 2,3-dihydroxy-5-({[(2R,3R,4R,5R,6S)-3,4,5,6-tetrakis[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]oxan-2-yl]methoxy}carbonyl)phenyl 3,4,5-trihydroxybenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122212542D          

122132  0  0  1  0            999 V2000
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

174184  0  0  0  0  0  0  0  0999 V2000
   -2.5959    0.7601    3.6642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4189   -0.4728    4.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309122212542D          

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M  END
> <DATABASE_ID>
NP0327909

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(=CC(O)=C1O)C(=O)OC1=CC(=CC(O)=C1O)C(=O)OC[C@H]1O[C@@H](OC(=O)C2=CC(O)=C(O)C(OC(=O)C3=CC(O)=C(O)C(O)=C3)=C2)[C@H](OC(=O)C2=CC(O)=C(O)C(OC(=O)C3=CC(O)=C(O)C(O)=C3)=C2)[C@H](OC(=O)C2=CC(O)=C(O)C(OC(=O)C3=CC(O)=C(O)C(O)=C3)=C2)[C@@H]1OC(=O)C1=CC(O)=C(O)C(OC(=O)C2=CC(O)=C(O)C(O)=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C76H52O46/c77-32-1-22(2-33(78)53(32)92)67(103)113-47-16-27(11-42(87)58(47)97)66(102)112-21-52-63(119-72(108)28-12-43(88)59(98)48(17-28)114-68(104)23-3-34(79)54(93)35(80)4-23)64(120-73(109)29-13-44(89)60(99)49(18-29)115-69(105)24-5-36(81)55(94)37(82)6-24)65(121-74(110)30-14-45(90)61(100)50(19-30)116-70(106)25-7-38(83)56(95)39(84)8-25)76(118-52)122-75(111)31-15-46(91)62(101)51(20-31)117-71(107)26-9-40(85)57(96)41(86)10-26/h1-20,52,63-65,76-101H,21H2/t52-,63-,64-,65-,76+/m1/s1

> <INCHI_KEY>
LRBQNJMCXXYXIU-JPZKJCTESA-N

> <FORMULA>
C76H52O46

> <MOLECULAR_WEIGHT>
1701.206

> <EXACT_MASS>
1700.172974194

> <JCHEM_ACCEPTOR_COUNT>
36

> <JCHEM_ATOM_COUNT>
174

> <JCHEM_AVERAGE_POLARIZABILITY>
153.49814708569954

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
25

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,5R,6R)-3,4,5-tris[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-6-{[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]methyl}oxan-2-yl 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate

> <JCHEM_LOGP>
13.512004047

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
11

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.059665938059188

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.605963885458599

> <JCHEM_PKA_STRONGEST_BASIC>
-4.773003704204116

> <JCHEM_POLAR_SURFACE_AREA>
777.9800000000005

> <JCHEM_REFRACTIVITY>
393.57039999999984

> <JCHEM_ROTATABLE_BOND_COUNT>
31

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5R,6R)-3,4,5-tris[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-6-{[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]methyl}oxan-2-yl 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000 -12.320   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.667 -18.480   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.335 -16.940   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.668 -16.170   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0     -12.003 -14.630   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0     -10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0     -12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.334 -16.170   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.667 -18.480   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.334 -19.250   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.334 -20.790   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -0.000 -21.560   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       2.667 -21.560   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       1.762 -22.806   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       4.001 -20.790   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       5.335 -21.560   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       5.335 -23.100   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       6.668 -23.870   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       4.001 -23.870   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       4.001 -25.410   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       2.667 -26.180   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       2.667 -27.720   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       1.334 -25.410   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -0.000 -26.180   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       1.334 -23.870   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      -0.000 -23.100   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       2.667 -23.100   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       4.001 -19.250   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0       5.335 -16.940   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0       8.002 -16.940   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       9.336 -16.170   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      10.669 -16.940   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      12.003 -16.170   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0      10.669 -18.480   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0      12.003 -19.250   0.000  0.00  0.00           O+0
HETATM   65  C   UNK     0       9.336 -19.250   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0       9.336 -20.790   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0      10.669 -21.560   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0      12.003 -20.790   0.000  0.00  0.00           O+0
HETATM   69  C   UNK     0      10.669 -23.100   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      12.003 -23.870   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      12.003 -25.410   0.000  0.00  0.00           C+0
HETATM   72  O   UNK     0      13.337 -26.180   0.000  0.00  0.00           O+0
HETATM   73  C   UNK     0      10.669 -26.180   0.000  0.00  0.00           C+0
HETATM   74  O   UNK     0      10.669 -27.720   0.000  0.00  0.00           O+0
HETATM   75  C   UNK     0       9.336 -25.410   0.000  0.00  0.00           C+0
HETATM   76  O   UNK     0       8.002 -26.180   0.000  0.00  0.00           O+0
HETATM   77  C   UNK     0       9.336 -23.870   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0       8.002 -18.480   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   80  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   81  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   82  O   UNK     0       8.002 -13.860   0.000  0.00  0.00           O+0
HETATM   83  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   86  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   87  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   88  O   UNK     0      13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   89  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   90  O   UNK     0      13.337 -12.320   0.000  0.00  0.00           O+0
HETATM   91  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   92  O   UNK     0      14.670 -10.010   0.000  0.00  0.00           O+0
HETATM   93  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   95  C   UNK     0      18.672 -12.320   0.000  0.00  0.00           C+0
HETATM   96  O   UNK     0      20.005 -11.550   0.000  0.00  0.00           O+0
HETATM   97  C   UNK     0      18.672 -13.860   0.000  0.00  0.00           C+0
HETATM   98  O   UNK     0      20.005 -14.630   0.000  0.00  0.00           O+0
HETATM   99  C   UNK     0      17.338 -14.630   0.000  0.00  0.00           C+0
HETATM  100  O   UNK     0      17.338 -16.170   0.000  0.00  0.00           O+0
HETATM  101  C   UNK     0      16.004 -13.860   0.000  0.00  0.00           C+0
HETATM  102  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM  103  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM  104  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM  105  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM  106  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM  107  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM  108  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM  109  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM  110  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM  111  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM  112  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM  113  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM  114  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM  115  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM  116  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM  117  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM  118  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM  119  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM  120  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM  121  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM  122  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3  103                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   79                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   31                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   30                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   30                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   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   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   21                                                       
CONECT   30   17   11                                                       
CONECT   31    7   32   55                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   54                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   54                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46   53                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   45                                                       
CONECT   54   41   35                                                       
CONECT   55   31   56   79                                                  
CONECT   56   55   57                                                       
CONECT   57   56   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   60   78                                                  
CONECT   60   59   61                                                       
CONECT   61   60   62   63                                                  
CONECT   62   61                                                            
CONECT   63   61   64   65                                                  
CONECT   64   63                                                            
CONECT   65   63   66   78                                                  
CONECT   66   65   67                                                       
CONECT   67   66   68   69                                                  
CONECT   68   67                                                            
CONECT   69   67   70   77                                                  
CONECT   70   69   71                                                       
CONECT   71   70   72   73                                                  
CONECT   72   71                                                            
CONECT   73   71   74   75                                                  
CONECT   74   73                                                            
CONECT   75   73   76   77                                                  
CONECT   76   75                                                            
CONECT   77   75   69                                                       
CONECT   78   65   59                                                       
CONECT   79   55    5   80                                                  
CONECT   80   79   81                                                       
CONECT   81   80   82   83                                                  
CONECT   82   81                                                            
CONECT   83   81   84  102                                                  
CONECT   84   83   85                                                       
CONECT   85   84   86   87                                                  
CONECT   86   85                                                            
CONECT   87   85   88   89                                                  
CONECT   88   87                                                            
CONECT   89   87   90  102                                                  
CONECT   90   89   91                                                       
CONECT   91   90   92   93                                                  
CONECT   92   91                                                            
CONECT   93   91   94  101                                                  
CONECT   94   93   95                                                       
CONECT   95   94   96   97                                                  
CONECT   96   95                                                            
CONECT   97   95   98   99                                                  
CONECT   98   97                                                            
CONECT   99   97  100  101                                                  
CONECT  100   99                                                            
CONECT  101   99   93                                                       
CONECT  102   89   83                                                       
CONECT  103    2  104  122                                                  
CONECT  104  103  105                                                       
CONECT  105  104  106  107                                                  
CONECT  106  105                                                            
CONECT  107  105  108  109                                                  
CONECT  108  107                                                            
CONECT  109  107  110  122                                                  
CONECT  110  109  111                                                       
CONECT  111  110  112  113                                                  
CONECT  112  111                                                            
CONECT  113  111  114  121                                                  
CONECT  114  113  115                                                       
CONECT  115  114  116  117                                                  
CONECT  116  115                                                            
CONECT  117  115  118  119                                                  
CONECT  118  117                                                            
CONECT  119  117  120  121                                                  
CONECT  120  119                                                            
CONECT  121  119  113                                                       
CONECT  122  109  103                                                       
MASTER        0    0    0    0    0    0    0    0  122    0  264    0
END

View in JSmol

Synonyms

Value	Source
2,3-Dihydroxy-5-({[(2R,3R,4R,5R,6S)-3,4,5,6-tetrakis[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]oxan-2-yl]methoxy}carbonyl)phenyl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₇₆H₅₂O₄₆

Average Mass

1701.2060 Da

Monoisotopic Mass

1700.17297 Da

IUPAC Name

(2S,3R,4R,5R,6R)-3,4,5-tris[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-6-{[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]methyl}oxan-2-yl 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate

Traditional Name

CAS Registry Number

Not Available

SMILES

OC1=CC(=CC(O)=C1O)C(=O)OC1=CC(=CC(O)=C1O)C(=O)OC[C@H]1O[C@@H](OC(=O)C2=CC(O)=C(O)C(OC(=O)C3=CC(O)=C(O)C(O)=C3)=C2)[C@H](OC(=O)C2=CC(O)=C(O)C(OC(=O)C3=CC(O)=C(O)C(O)=C3)=C2)[C@H](OC(=O)C2=CC(O)=C(O)C(OC(=O)C3=CC(O)=C(O)C(O)=C3)=C2)[C@@H]1OC(=O)C1=CC(O)=C(O)C(OC(=O)C2=CC(O)=C(O)C(O)=C2)=C1

InChI Identifier

InChI=1S/C76H52O46/c77-32-1-22(2-33(78)53(32)92)67(103)113-47-16-27(11-42(87)58(47)97)66(102)112-21-52-63(119-72(108)28-12-43(88)59(98)48(17-28)114-68(104)23-3-34(79)54(93)35(80)4-23)64(120-73(109)29-13-44(89)60(99)49(18-29)115-69(105)24-5-36(81)55(94)37(82)6-24)65(121-74(110)30-14-45(90)61(100)50(19-30)116-70(106)25-7-38(83)56(95)39(84)8-25)76(118-52)122-75(111)31-15-46(91)62(101)51(20-31)117-71(107)26-9-40(85)57(96)41(86)10-26/h1-20,52,63-65,76-101H,21H2/t52-,63-,64-,65-,76+/m1/s1

InChI Key

LRBQNJMCXXYXIU-JPZKJCTESA-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
Achillea millefolium	LOTUS Database	35616633
Camellia sinensis	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
Depside backbone
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Phenol ester
Benzoate ester
Pyrogallol derivative
Benzoic acid or derivatives
Benzenetriol
Phenoxy compound
Catechol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	13.51	ChemAxon
pKa (Strongest Acidic)	7.61	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	36	ChemAxon
Hydrogen Donor Count	25	ChemAxon
Polar Surface Area	777.98 Å²	ChemAxon
Rotatable Bond Count	31	ChemAxon
Refractivity	393.57 m³·mol⁻¹	ChemAxon
Polarizability	153.5 Å³	ChemAxon
Number of Rings	11	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

Not Available

Chemspider ID

78430661

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134129492

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4r,5r,6r)-3,4,5-tris[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-6-{[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]methyl}oxan-2-yl 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate (NP0327909)

MOL for NP0327909 ((2s,3r,4r,5r,6r)-3,4,5-tris[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-6-{[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]methyl}oxan-2-yl 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate)

3D MOL for NP0327909 ((2s,3r,4r,5r,6r)-3,4,5-tris[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-6-{[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]methyl}oxan-2-yl 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate)

3D SDF for NP0327909 ((2s,3r,4r,5r,6r)-3,4,5-tris[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-6-{[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]methyl}oxan-2-yl 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate)

3D-SDF for NP0327909 ((2s,3r,4r,5r,6r)-3,4,5-tris[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-6-{[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]methyl}oxan-2-yl 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate)

PDB for NP0327909 ((2s,3r,4r,5r,6r)-3,4,5-tris[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-6-{[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]methyl}oxan-2-yl 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate)

3D PDB for NP0327909 ((2s,3r,4r,5r,6r)-3,4,5-tris[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-6-{[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]methyl}oxan-2-yl 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate)

SMILES for NP0327909 ((2s,3r,4r,5r,6r)-3,4,5-tris[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-6-{[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]methyl}oxan-2-yl 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate)

INCHI for NP0327909 ((2s,3r,4r,5r,6r)-3,4,5-tris[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-6-{[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]methyl}oxan-2-yl 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate)

Structure for NP0327909 ((2s,3r,4r,5r,6r)-3,4,5-tris[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-6-{[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]methyl}oxan-2-yl 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate)

3D Structure for NP0327909 ((2s,3r,4r,5r,6r)-3,4,5-tris[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-6-{[3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]methyl}oxan-2-yl 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate)