NP-MRD: Showing NP-Card for (2s,3r,4s,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 (NP0232000)

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Record Information

Version

2.0

Created at

2022-09-06 13:05:03 UTC

Updated at

2022-09-06 13:05:03 UTC

NP-MRD ID

NP0232000

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,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

TANNIC ACID, also known as acids, tannic or tannate, 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,4s,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 Acacia mearnsii, Anchomanes difformis, Calluna vulgaris, Ephedra gerardiana, Erodium cicutarium, Hamamelis virginiana, Phaseolus vulgaris, Potentilla chrysantha, Quercus infectoria, Schinopsis balansae, Shorea maxwelliana, Terminalia chebula and Vachellia rigidula. TANNIC ACID is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1572004201615512D          

127137  0  0  1  0            999 V2000
   -3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   14.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   13.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.0039    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.7184    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5749    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315   10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.7158    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   13.6125    0.0000 C   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
    4.5947   -1.3826    2.4116 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1572004201615512D          

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M  END
> <DATABASE_ID>
NP0232000

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(COC(=O)C2=CC(O)=C(O)C(OC(=O)C3=CC(O)=C(O)C(O)=C3)=C2)O[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@]1([H])OC(=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-PPKXGCFTSA-N

> <FORMULA>
C76H52O46

> <MOLECULAR_WEIGHT>
1701.206

> <EXACT_MASS>
1700.172974194

> <JCHEM_ACCEPTOR_COUNT>
36

> <JCHEM_ATOM_COUNT>
174

> <JCHEM_AVERAGE_POLARIZABILITY>
159.31420845840745

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
25

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3-dihydroxy-5-({[(2R,3R,4S,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

> <ALOGPS_LOGP>
4.73

> <JCHEM_LOGP>
13.512004047

> <ALOGPS_LOGS>
-3.62

> <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>
777.9800000000008

> <JCHEM_REFRACTIVITY>
393.5703999999992

> <JCHEM_ROTATABLE_BOND_COUNT>
31

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-dihydroxy-5-({[(2R,3R,4S,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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-16         0                                  
HETATM    1  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.336   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -12.003  26.950   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.669  24.640   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -28.007  16.170   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -29.341  18.480   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -22.673   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -25.340   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -16.004   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -17.338   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.336  16.170   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -17.338  20.790   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -21.339  20.020   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -22.673  11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -14.670   8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -10.669  13.860   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -14.670  20.790   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -22.673  17.710   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -21.339   9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -17.338   8.470   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -14.670  16.170   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -12.003  25.410   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -28.007  17.710   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -24.006   4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -17.338   3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -10.669  15.400   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -16.004  20.020   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -21.339  18.480   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -21.339  10.780   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -16.004   9.240   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -10.669  27.720   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -9.336  25.410   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -29.341  15.400   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -30.675  17.710   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -22.673   2.310   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -25.340   2.310   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -14.670   3.850   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -16.004   1.540   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -8.002  15.400   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -17.338  22.330   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -22.673  20.790   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -24.006  10.780   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -14.670   6.930   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -9.336  13.090   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -14.670  22.330   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -24.006  18.480   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -22.673   8.470   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0     -17.338   6.930   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0     -16.004  15.400   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -9.336  26.950   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0     -30.675  16.170   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0     -24.006   1.540   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0     -14.670   2.310   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -8.002  13.860   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0     -16.004  23.100   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0     -24.006  20.020   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0     -24.006   9.240   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0     -16.004   6.160   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0     -17.338  16.170   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0     -18.672  15.400   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0     -18.672  13.860   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0     -12.003  16.170   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      -8.002  10.780   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0     -13.337  24.640   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0     -26.674  18.480   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0     -24.006   6.160   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0     -18.672   4.620   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0     -16.004  18.480   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0     -20.005  17.710   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0     -20.005  11.550   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0     -16.004  10.780   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0     -17.338  13.090   0.000  0.00  0.00           C+0
HETATM   77  O   UNK     0      -5.335   6.160   0.000  0.00  0.00           O+0
HETATM   78  O   UNK     0     -10.669   6.160   0.000  0.00  0.00           O+0
HETATM   79  O   UNK     0     -10.669  29.260   0.000  0.00  0.00           O+0
HETATM   80  O   UNK     0      -8.002  24.640   0.000  0.00  0.00           O+0
HETATM   81  O   UNK     0     -29.341  13.860   0.000  0.00  0.00           O+0
HETATM   82  O   UNK     0     -32.008  18.480   0.000  0.00  0.00           O+0
HETATM   83  O   UNK     0     -21.339   1.540   0.000  0.00  0.00           O+0
HETATM   84  O   UNK     0     -26.674   1.540   0.000  0.00  0.00           O+0
HETATM   85  O   UNK     0     -13.337   4.620   0.000  0.00  0.00           O+0
HETATM   86  O   UNK     0     -16.004   0.000   0.000  0.00  0.00           O+0
HETATM   87  O   UNK     0      -6.668  16.170   0.000  0.00  0.00           O+0
HETATM   88  O   UNK     0     -18.672  23.100   0.000  0.00  0.00           O+0
HETATM   89  O   UNK     0     -22.673  22.330   0.000  0.00  0.00           O+0
HETATM   90  O   UNK     0     -25.340  11.550   0.000  0.00  0.00           O+0
HETATM   91  O   UNK     0     -13.337   6.160   0.000  0.00  0.00           O+0
HETATM   92  O   UNK     0      -8.002   4.620   0.000  0.00  0.00           O+0
HETATM   93  O   UNK     0      -8.002  27.720   0.000  0.00  0.00           O+0
HETATM   94  O   UNK     0     -32.008  15.400   0.000  0.00  0.00           O+0
HETATM   95  O   UNK     0     -24.006   0.000   0.000  0.00  0.00           O+0
HETATM   96  O   UNK     0     -13.337   1.540   0.000  0.00  0.00           O+0
HETATM   97  O   UNK     0      -6.668  13.090   0.000  0.00  0.00           O+0
HETATM   98  O   UNK     0     -16.004  24.640   0.000  0.00  0.00           O+0
HETATM   99  O   UNK     0     -25.340  20.790   0.000  0.00  0.00           O+0
HETATM  100  O   UNK     0     -25.340   8.470   0.000  0.00  0.00           O+0
HETATM  101  O   UNK     0     -15.099   4.914   0.000  0.00  0.00           O+0
HETATM  102  O   UNK     0     -12.003  17.710   0.000  0.00  0.00           O+0
HETATM  103  O   UNK     0      -6.668  11.550   0.000  0.00  0.00           O+0
HETATM  104  O   UNK     0     -14.670  25.410   0.000  0.00  0.00           O+0
HETATM  105  O   UNK     0     -26.674  20.020   0.000  0.00  0.00           O+0
HETATM  106  O   UNK     0     -25.340   6.930   0.000  0.00  0.00           O+0
HETATM  107  O   UNK     0     -20.005   3.850   0.000  0.00  0.00           O+0
HETATM  108  O   UNK     0     -14.670  17.710   0.000  0.00  0.00           O+0
HETATM  109  O   UNK     0     -18.672  18.480   0.000  0.00  0.00           O+0
HETATM  110  O   UNK     0     -18.672  10.780   0.000  0.00  0.00           O+0
HETATM  111  O   UNK     0     -14.670  11.550   0.000  0.00  0.00           O+0
HETATM  112  O   UNK     0     -13.337  15.400   0.000  0.00  0.00           O+0
HETATM  113  O   UNK     0      -9.336  11.550   0.000  0.00  0.00           O+0
HETATM  114  O   UNK     0     -13.337  23.100   0.000  0.00  0.00           O+0
HETATM  115  O   UNK     0     -25.340  17.710   0.000  0.00  0.00           O+0
HETATM  116  O   UNK     0     -22.673   6.930   0.000  0.00  0.00           O+0
HETATM  117  O   UNK     0     -18.672   6.160   0.000  0.00  0.00           O+0
HETATM  118  O   UNK     0     -16.004  13.860   0.000  0.00  0.00           O+0
HETATM  119  O   UNK     0     -17.338  17.710   0.000  0.00  0.00           O+0
HETATM  120  O   UNK     0     -20.005  16.170   0.000  0.00  0.00           O+0
HETATM  121  O   UNK     0     -20.005  13.090   0.000  0.00  0.00           O+0
HETATM  122  O   UNK     0     -17.338  11.550   0.000  0.00  0.00           O+0
HETATM  123  H   UNK     0     -16.004  16.940   0.000  0.00  0.00           H+0
HETATM  124  H   UNK     0     -18.672  16.940   0.000  0.00  0.00           H+0
HETATM  125  H   UNK     0     -17.338  14.630   0.000  0.00  0.00           H+0
HETATM  126  H   UNK     0     -20.005  14.630   0.000  0.00  0.00           H+0
HETATM  127  H   UNK     0     -18.672  12.320   0.000  0.00  0.00           H+0
CONECT    1   22   32                                                       
CONECT    2   22   33                                                       
CONECT    3   23   34                                                       
CONECT    4   23   35                                                       
CONECT    5   24   36                                                       
CONECT    6   24   37                                                       
CONECT    7   25   38                                                       
CONECT    8   25   39                                                       
CONECT    9   26   40                                                       
CONECT   10   26   41                                                       
CONECT   11   27   42                                                       
CONECT   12   28   43                                                       
CONECT   13   29   44                                                       
CONECT   14   30   45                                                       
CONECT   15   31   46                                                       
CONECT   16   27   47                                                       
CONECT   17   28   48                                                       
CONECT   18   29   49                                                       
CONECT   19   30   50                                                       
CONECT   20   31   51                                                       
CONECT   21   52  112                                                       
CONECT   22    1    2   67                                                  
CONECT   23    3    4   68                                                  
CONECT   24    5    6   69                                                  
CONECT   25    7    8   70                                                  
CONECT   26    9   10   71                                                  
CONECT   27   11   16   66                                                  
CONECT   28   12   17   72                                                  
CONECT   29   13   18   73                                                  
CONECT   30   14   19   74                                                  
CONECT   31   15   20   75                                                  
CONECT   32    1   53   77                                                  
CONECT   33    2   53   78                                                  
CONECT   34    3   54   79                                                  
CONECT   35    4   54   80                                                  
CONECT   36    5   55   81                                                  
CONECT   37    6   55   82                                                  
CONECT   38    7   56   83                                                  
CONECT   39    8   56   84                                                  
CONECT   40    9   57   85                                                  
CONECT   41   10   57   86                                                  
CONECT   42   11   58   87                                                  
CONECT   43   12   59   88                                                  
CONECT   44   13   60   89                                                  
CONECT   45   14   61   90                                                  
CONECT   46   15   62   91                                                  
CONECT   47   16   58  113                                                  
CONECT   48   17   59  114                                                  
CONECT   49   18   60  115                                                  
CONECT   50   19   61  116                                                  
CONECT   51   20   62  117                                                  
CONECT   52   21   63  118  123                                             
CONECT   53   32   33   92                                                  
CONECT   54   34   35   93                                                  
CONECT   55   36   37   94                                                  
CONECT   56   38   39   95                                                  
CONECT   57   40   41   96                                                  
CONECT   58   42   47   97                                                  
CONECT   59   43   48   98                                                  
CONECT   60   44   49   99                                                  
CONECT   61   45   50  100                                                  
CONECT   62   46   51  101                                                  
CONECT   63   52   64  119  124                                             
CONECT   64   63   65  120  125                                             
CONECT   65   64   76  121  126                                             
CONECT   66   27  102  112                                                  
CONECT   67   22  103  113                                                  
CONECT   68   23  104  114                                                  
CONECT   69   24  105  115                                                  
CONECT   70   25  106  116                                                  
CONECT   71   26  107  117                                                  
CONECT   72   28  108  119                                                  
CONECT   73   29  109  120                                                  
CONECT   74   30  110  121                                                  
CONECT   75   31  111  122                                                  
CONECT   76   65  118  122  127                                             
CONECT   77   32                                                            
CONECT   78   33                                                            
CONECT   79   34                                                            
CONECT   80   35                                                            
CONECT   81   36                                                            
CONECT   82   37                                                            
CONECT   83   38                                                            
CONECT   84   39                                                            
CONECT   85   40                                                            
CONECT   86   41                                                            
CONECT   87   42                                                            
CONECT   88   43                                                            
CONECT   89   44                                                            
CONECT   90   45                                                            
CONECT   91   46                                                            
CONECT   92   53                                                            
CONECT   93   54                                                            
CONECT   94   55                                                            
CONECT   95   56                                                            
CONECT   96   57                                                            
CONECT   97   58                                                            
CONECT   98   59                                                            
CONECT   99   60                                                            
CONECT  100   61                                                            
CONECT  101   62                                                            
CONECT  102   66                                                            
CONECT  103   67                                                            
CONECT  104   68                                                            
CONECT  105   69                                                            
CONECT  106   70                                                            
CONECT  107   71                                                            
CONECT  108   72                                                            
CONECT  109   73                                                            
CONECT  110   74                                                            
CONECT  111   75                                                            
CONECT  112   21   66                                                       
CONECT  113   47   67                                                       
CONECT  114   48   68                                                       
CONECT  115   49   69                                                       
CONECT  116   50   70                                                       
CONECT  117   51   71                                                       
CONECT  118   52   76                                                       
CONECT  119   63   72                                                       
CONECT  120   64   73                                                       
CONECT  121   65   74                                                       
CONECT  122   75   76                                                       
CONECT  123   52                                                            
CONECT  124   63                                                            
CONECT  125   64                                                            
CONECT  126   65                                                            
CONECT  127   76                                                            
MASTER        0    0    0    0    0    0    0    0  127    0  274    0
END

View in JSmol

Synonyms

Value	Source
TANNate	Generator
Acids, tannic	MeSH
Tannic acids	MeSH
Tannins	MeSH
Acid, tannic	MeSH
e181	ChEMBL
2,3-Dihydroxy-5-({[(2R,3R,4S,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
Tannic acid	MeSH

Chemical Formula

C₇₆H₅₂O₄₆

Average Mass

1701.2060 Da

Monoisotopic Mass

1700.17297 Da

IUPAC Name

2,3-dihydroxy-5-({[(2R,3R,4S,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

Traditional Name

2,3-dihydroxy-5-({[(2R,3R,4S,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

CAS Registry Number

Not Available

SMILES

[H][C@]1(COC(=O)C2=CC(O)=C(O)C(OC(=O)C3=CC(O)=C(O)C(O)=C3)=C2)O[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@]1([H])OC(=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-PPKXGCFTSA-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
Acacia mearnsii	LOTUS Database	35616633
Anchomanes difformis	LOTUS Database	35616633
Calluna vulgaris	LOTUS Database	35616633
Ephedra gerardiana	LOTUS Database	35616633
Erodium cicutarium	LOTUS Database	35616633
Hamamelis virginiana	LOTUS Database	35616633
Phaseolus vulgaris	LOTUS Database	35616633
Potentilla chrysantha	LOTUS Database	35616633
Quercus infectoria	LOTUS Database	35616633
Schinopsis balansae	LOTUS Database	35616633
Shorea maxwelliana	LOTUS Database	35616633
Terminalia chebula	LOTUS Database	35616633
Vachellia rigidula	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
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
Phenoxy compound
Catechol
Benzoyl
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monosaccharide
Oxane
Benzenoid
Monocyclic benzene moiety
Carboxylic acid ester
Polyol
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

tannin (CHEBI:81066 )

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	4.73	ALOGPS
logP	13.51	ChemAxon
logS	-3.6	ALOGPS
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	159.31 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

Not Available

KEGG Compound ID

C17409

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16129778

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,4s,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 (NP0232000)

MOL for NP0232000 ((2s,3r,4s,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 NP0232000 ((2s,3r,4s,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 NP0232000 ((2s,3r,4s,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 NP0232000 ((2s,3r,4s,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 NP0232000 ((2s,3r,4s,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 NP0232000 ((2s,3r,4s,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 NP0232000 ((2s,3r,4s,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 NP0232000 ((2s,3r,4s,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 NP0232000 ((2s,3r,4s,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 NP0232000 ((2s,3r,4s,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)