NP-MRD: Showing NP-Card for Woodfordin A (NP0074309)

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Record Information

Version

2.0

Created at

2022-04-28 19:27:52 UTC

Updated at

2022-04-28 19:27:52 UTC

NP-MRD ID

NP0074309

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Woodfordin A

Description

(2S,3R,4S,5R,6R)-5-hydroxy-2,4-bis(3,4,5-trihydroxybenzoyloxy)-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-3-yl 3,4,5-trihydroxy-2-{[(10R,11R,12S,13R,15S)-3,4,5,22,23-pentahydroxy-8,18-dioxo-11,12,13-tris(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]Tricosa-1(23),2,4,6,19,21-hexaen-21-yl]oxy}benzoate 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. Woodfordin A is found in Woodfordia fruticosa . Based on a literature review very few articles have been published on (2S,3R,4S,5R,6R)-5-hydroxy-2,4-bis(3,4,5-trihydroxybenzoyloxy)-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-3-yl 3,4,5-trihydroxy-2-{[(10R,11R,12S,13R,15S)-3,4,5,22,23-pentahydroxy-8,18-dioxo-11,12,13-tris(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]Tricosa-1(23),2,4,6,19,21-hexaen-21-yl]oxy}benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221272D          

123134  0  0  1  0            999 V2000
    8.3054    0.6655    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    6.7705    1.2712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8920    0.4552    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6594    0.1523    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7808   -0.6637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5482   -0.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.1451   -3.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6769    3.1712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
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  6  7  1  6  0  0  0
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M  END

     RDKit          3D

179190  0  0  0  0  0  0  0  0999 V2000
   -8.7299    3.5273   -2.7500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3627    3.7881   -1.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2032    3.2715   -1.0002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4041    2.3983   -1.7202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0182    2.1427   -1.1683 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282221272D          

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M  END
> <DATABASE_ID>
NP0074309

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](COC(=O)C2=CC(O)=C(O)C(O)=C2)O[C@@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@H](OC(=O)C2=C(OC3=CC4=C(C(O)=C3O)C3=C(C=C(O)C(O)=C3O)C(=O)O[C@@H]3[C@H](COC4=O)O[C@H](OC(=O)C4=CC(O)=C(O)C(O)=C4)[C@@H](OC(=O)C4=CC(O)=C(O)C(O)=C4)[C@@H]3OC(=O)C3=CC(O)=C(O)C(O)=C3)C(O)=C(O)C(O)=C2)[C@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C75H56O48/c76-27-1-18(2-28(77)46(27)90)65(103)112-16-42-55(99)61(118-66(104)19-3-29(78)47(91)30(79)4-19)63(74(115-42)122-69(107)22-9-35(84)50(94)36(85)10-22)121-73(111)26-14-40(89)53(97)58(102)59(26)114-41-15-25-45(57(101)54(41)98)44-24(13-39(88)52(96)56(44)100)72(110)117-60-43(17-113-71(25)109)116-75(123-70(108)23-11-37(86)51(95)38(87)12-23)64(120-68(106)21-7-33(82)49(93)34(83)8-21)62(60)119-67(105)20-5-31(80)48(92)32(81)6-20/h1-15,42-43,55,60-64,74-102H,16-17H2/t42-,43+,55-,60-,61+,62-,63-,64+,74+,75-/m1/s1

> <INCHI_KEY>
HUDRVRFMJDNTKX-VOWKTHRLSA-N

> <FORMULA>
C75H56O48

> <MOLECULAR_WEIGHT>
1725.225

> <EXACT_MASS>
1724.194103563

> <JCHEM_ACCEPTOR_COUNT>
38

> <JCHEM_ATOM_COUNT>
179

> <JCHEM_AVERAGE_POLARIZABILITY>
153.67925133318778

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
27

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6R)-5-hydroxy-2,4-bis(3,4,5-trihydroxybenzoyloxy)-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-3-yl 3,4,5-trihydroxy-2-{[(10R,11R,12S,13R,15S)-3,4,5,22,23-pentahydroxy-8,18-dioxo-11,12,13-tris(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0^{2,7}.0^{10,15}]tricosa-1(19),2(7),3,5,20,22-hexaen-21-yl]oxy}benzoate

> <ALOGPS_LOGP>
4.26

> <JCHEM_LOGP>
7.500942751666667

> <ALOGPS_LOGS>
-3.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
12

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
7.276349606282258

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.570391900299793

> <JCHEM_PKA_STRONGEST_BASIC>
-5.910949244237174

> <JCHEM_POLAR_SURFACE_AREA>
810.6000000000005

> <JCHEM_REFRACTIVITY>
391.0091999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6R)-5-hydroxy-2,4-bis(3,4,5-trihydroxybenzoyloxy)-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-3-yl 3,4,5-trihydroxy-2-{[(10R,11R,12S,13R,15S)-3,4,5,22,23-pentahydroxy-8,18-dioxo-11,12,13-tris(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0^{2,7}.0^{10,15}]tricosa-1(19),2(7),3,5,20,22-hexaen-21-yl]oxy}benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      15.503   1.242   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.277   2.765   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      13.844   3.331   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      12.638   2.373   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.865   0.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.298   0.284   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      14.524  -1.239   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      15.957  -1.804   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      17.162  -0.846   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      16.183  -3.327   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.616  -3.893   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.842  -5.416   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.637  -6.374   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.204  -5.809   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.978  -4.285   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.998  -6.767   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      16.863  -7.897   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      19.275  -5.981   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      12.232  -0.554   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.941  -1.393   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.382  -2.869   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.401  -1.401   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.101  -0.575   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.455   0.823   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.666   2.348   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.669   3.517   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.830   4.809   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      10.144   3.958   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      11.624   3.532   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.451   3.294   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.024   2.715   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.424   1.421   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.028   0.244   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.816  -1.282   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       3.999  -0.118   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       3.809   3.661   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.021   5.186   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.805   6.132   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.017   7.658   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.444   8.237   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.659   7.291   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       5.447   5.766   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       6.663   4.820   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       7.086   7.871   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       4.656   9.763   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       1.379   5.553   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       1.167   4.028   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       0.163   6.499   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      -1.263   5.920   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -1.475   4.394   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -2.902   3.815   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -4.117   4.761   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      -3.906   6.286   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      -2.479   6.866   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      -2.267   8.391   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      -3.482   9.337   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      -4.909   8.758   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      -3.271  10.862   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      -4.486  11.808   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      -4.274  13.334   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      -2.847  13.913   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      -1.632  12.967   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      -1.844  11.442   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0      -0.205  13.546   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      -2.636  15.438   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0      -5.489  14.280   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0      -5.544   4.181   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0      -6.759   5.127   0.000  0.00  0.00           O+0
HETATM   69  C   UNK     0      -8.186   4.548   0.000  0.00  0.00           C+0
HETATM   70  O   UNK     0      -8.398   3.023   0.000  0.00  0.00           O+0
HETATM   71  C   UNK     0      -9.401   5.494   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0     -10.828   4.915   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0     -12.043   5.861   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0     -11.832   7.386   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0     -10.405   7.965   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      -9.190   7.019   0.000  0.00  0.00           C+0
HETATM   77  O   UNK     0     -10.193   9.491   0.000  0.00  0.00           O+0
HETATM   78  O   UNK     0     -13.047   8.332   0.000  0.00  0.00           O+0
HETATM   79  O   UNK     0     -13.470   5.281   0.000  0.00  0.00           O+0
HETATM   80  O   UNK     0      -3.114   2.289   0.000  0.00  0.00           O+0
HETATM   81  O   UNK     0      -0.260   3.448   0.000  0.00  0.00           O+0
HETATM   82  C   UNK     0      -0.472   1.923   0.000  0.00  0.00           C+0
HETATM   83  O   UNK     0      -1.898   1.343   0.000  0.00  0.00           O+0
HETATM   84  C   UNK     0       0.744   0.977   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0       2.170   1.556   0.000  0.00  0.00           C+0
HETATM   86  C   UNK     0       3.386   0.610   0.000  0.00  0.00           C+0
HETATM   87  C   UNK     0       3.174  -0.915   0.000  0.00  0.00           C+0
HETATM   88  C   UNK     0       1.747  -1.495   0.000  0.00  0.00           C+0
HETATM   89  C   UNK     0       0.532  -0.549   0.000  0.00  0.00           C+0
HETATM   90  O   UNK     0       1.535  -3.020   0.000  0.00  0.00           O+0
HETATM   91  O   UNK     0       4.389  -1.861   0.000  0.00  0.00           O+0
HETATM   92  O   UNK     0       4.812   1.190   0.000  0.00  0.00           O+0
HETATM   93  C   UNK     0       6.736  -1.287   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0       6.670  -2.826   0.000  0.00  0.00           C+0
HETATM   95  C   UNK     0       7.970  -3.652   0.000  0.00  0.00           C+0
HETATM   96  C   UNK     0       9.335  -2.939   0.000  0.00  0.00           C+0
HETATM   97  O   UNK     0       7.904  -5.190   0.000  0.00  0.00           O+0
HETATM   98  O   UNK     0       5.305  -3.538   0.000  0.00  0.00           O+0
HETATM   99  O   UNK     0       5.304  -1.853   0.000  0.00  0.00           O+0
HETATM  100  O   UNK     0      16.482   3.723   0.000  0.00  0.00           O+0
HETATM  101  C   UNK     0      16.256   5.247   0.000  0.00  0.00           C+0
HETATM  102  O   UNK     0      14.823   5.812   0.000  0.00  0.00           O+0
HETATM  103  C   UNK     0      17.462   6.205   0.000  0.00  0.00           C+0
HETATM  104  C   UNK     0      17.235   7.728   0.000  0.00  0.00           C+0
HETATM  105  C   UNK     0      18.441   8.686   0.000  0.00  0.00           C+0
HETATM  106  C   UNK     0      19.873   8.120   0.000  0.00  0.00           C+0
HETATM  107  C   UNK     0      20.100   6.597   0.000  0.00  0.00           C+0
HETATM  108  C   UNK     0      18.894   5.639   0.000  0.00  0.00           C+0
HETATM  109  O   UNK     0      21.532   6.032   0.000  0.00  0.00           O+0
HETATM  110  O   UNK     0      21.079   9.078   0.000  0.00  0.00           O+0
HETATM  111  O   UNK     0      18.214  10.209   0.000  0.00  0.00           O+0
HETATM  112  O   UNK     0      16.936   0.677   0.000  0.00  0.00           O+0
HETATM  113  C   UNK     0      18.142   1.635   0.000  0.00  0.00           C+0
HETATM  114  O   UNK     0      17.915   3.158   0.000  0.00  0.00           O+0
HETATM  115  C   UNK     0      19.574   1.070   0.000  0.00  0.00           C+0
HETATM  116  C   UNK     0      20.780   2.027   0.000  0.00  0.00           C+0
HETATM  117  C   UNK     0      22.212   1.462   0.000  0.00  0.00           C+0
HETATM  118  C   UNK     0      22.439  -0.061   0.000  0.00  0.00           C+0
HETATM  119  C   UNK     0      21.233  -1.019   0.000  0.00  0.00           C+0
HETATM  120  C   UNK     0      19.801  -0.454   0.000  0.00  0.00           C+0
HETATM  121  O   UNK     0      21.460  -2.542   0.000  0.00  0.00           O+0
HETATM  122  O   UNK     0      23.872  -0.626   0.000  0.00  0.00           O+0
HETATM  123  O   UNK     0      23.418   2.420   0.000  0.00  0.00           O+0
CONECT    1    2    6  112                                                  
CONECT    2    1    3  100                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   29                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   10                                                       
CONECT   16   14                                                            
CONECT   17   13                                                            
CONECT   18   12                                                            
CONECT   19    5   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   96                                                  
CONECT   23   22   24   93                                                  
CONECT   24   23   25   33                                                  
CONECT   25   24   26   30                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28    4                                                       
CONECT   30   25   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33   35                                                  
CONECT   33   32   24   34                                                  
CONECT   34   33                                                            
CONECT   35   32                                                            
CONECT   36   31   37                                                       
CONECT   37   36   38   42                                                  
CONECT   38   37   39   46                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   45                                                  
CONECT   41   40   42   44                                                  
CONECT   42   41   37   43                                                  
CONECT   43   42                                                            
CONECT   44   41                                                            
CONECT   45   40                                                            
CONECT   46   38   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49                                                       
CONECT   49   48   50   54                                                  
CONECT   50   49   51   81                                                  
CONECT   51   50   52   80                                                  
CONECT   52   51   53   67                                                  
CONECT   53   52   54                                                       
CONECT   54   53   49   55                                                  
CONECT   55   54   56                                                       
CONECT   56   55   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   59   63                                                  
CONECT   59   58   60                                                       
CONECT   60   59   61   66                                                  
CONECT   61   60   62   65                                                  
CONECT   62   61   63   64                                                  
CONECT   63   62   58                                                       
CONECT   64   62                                                            
CONECT   65   61                                                            
CONECT   66   60                                                            
CONECT   67   52   68                                                       
CONECT   68   67   69                                                       
CONECT   69   68   70   71                                                  
CONECT   70   69                                                            
CONECT   71   69   72   76                                                  
CONECT   72   71   73                                                       
CONECT   73   72   74   79                                                  
CONECT   74   73   75   78                                                  
CONECT   75   74   76   77                                                  
CONECT   76   75   71                                                       
CONECT   77   75                                                            
CONECT   78   74                                                            
CONECT   79   73                                                            
CONECT   80   51                                                            
CONECT   81   50   82                                                       
CONECT   82   81   83   84                                                  
CONECT   83   82                                                            
CONECT   84   82   85   89                                                  
CONECT   85   84   86                                                       
CONECT   86   85   87   92                                                  
CONECT   87   86   88   91                                                  
CONECT   88   87   89   90                                                  
CONECT   89   88   84                                                       
CONECT   90   88                                                            
CONECT   91   87                                                            
CONECT   92   86                                                            
CONECT   93   23   94   99                                                  
CONECT   94   93   95   98                                                  
CONECT   95   94   96   97                                                  
CONECT   96   95   22                                                       
CONECT   97   95                                                            
CONECT   98   94                                                            
CONECT   99   93                                                            
CONECT  100    2  101                                                       
CONECT  101  100  102  103                                                  
CONECT  102  101                                                            
CONECT  103  101  104  108                                                  
CONECT  104  103  105                                                       
CONECT  105  104  106  111                                                  
CONECT  106  105  107  110                                                  
CONECT  107  106  108  109                                                  
CONECT  108  107  103                                                       
CONECT  109  107                                                            
CONECT  110  106                                                            
CONECT  111  105                                                            
CONECT  112    1  113                                                       
CONECT  113  112  114  115                                                  
CONECT  114  113                                                            
CONECT  115  113  116  120                                                  
CONECT  116  115  117                                                       
CONECT  117  116  118  123                                                  
CONECT  118  117  119  122                                                  
CONECT  119  118  120  121                                                  
CONECT  120  119  115                                                       
CONECT  121  119                                                            
CONECT  122  118                                                            
CONECT  123  117                                                            
MASTER        0    0    0    0    0    0    0    0  123    0  268    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4S,5R,6R)-5-Hydroxy-2,4-bis(3,4,5-trihydroxybenzoyloxy)-6-[(3,4,5-trihydroxybenzoyloxy)methyl]oxan-3-yl 3,4,5-trihydroxy-2-{[(10R,11R,12S,13R,15S)-3,4,5,22,23-pentahydroxy-8,18-dioxo-11,12,13-tris(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0,.0,]tricosa-1(23),2,4,6,19,21-hexaen-21-yl]oxy}benzoic acid	Generator

Chemical Formula

C₇₅H₅₆O₄₈

Average Mass

1725.2250 Da

Monoisotopic Mass

1724.19410 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](COC(=O)C2=CC(O)=C(O)C(O)=C2)O[C@@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@H](OC(=O)C2=C(OC3=CC4=C(C(O)=C3O)C3=C(C=C(O)C(O)=C3O)C(=O)O[C@@H]3[C@H](COC4=O)O[C@H](OC(=O)C4=CC(O)=C(O)C(O)=C4)[C@@H](OC(=O)C4=CC(O)=C(O)C(O)=C4)[C@@H]3OC(=O)C3=CC(O)=C(O)C(O)=C3)C(O)=C(O)C(O)=C2)[C@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C75H56O48/c76-27-1-18(2-28(77)46(27)90)65(103)112-16-42-55(99)61(118-66(104)19-3-29(78)47(91)30(79)4-19)63(74(115-42)122-69(107)22-9-35(84)50(94)36(85)10-22)121-73(111)26-14-40(89)53(97)58(102)59(26)114-41-15-25-45(57(101)54(41)98)44-24(13-39(88)52(96)56(44)100)72(110)117-60-43(17-113-71(25)109)116-75(123-70(108)23-11-37(86)51(95)38(87)12-23)64(120-68(106)21-7-33(82)49(93)34(83)8-21)62(60)119-67(105)20-5-31(80)48(92)32(81)6-20/h1-15,42-43,55,60-64,74-102H,16-17H2/t42-,43+,55-,60-,61+,62-,63-,64+,74+,75-/m1/s1

InChI Key

HUDRVRFMJDNTKX-VOWKTHRLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Woodfordia fruticosa	Plant	KNApSAcK

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
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Diaryl ether
Benzoate ester
Pyrogallol derivative
Benzoic acid or derivatives
Benzenetriol
Phenoxy compound
Phenol ether
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	4.26	ALOGPS
logP	7.5	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	6.57	ChemAxon
pKa (Strongest Basic)	-5.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	38	ChemAxon
Hydrogen Donor Count	27	ChemAxon
Polar Surface Area	810.6 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	391.01 m³·mol⁻¹	ChemAxon
Polarizability	153.68 Å³	ChemAxon
Number of Rings	12	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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162974012

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Woodfordin A (NP0074309)

MOL for NP0074309 (Woodfordin A)

3D MOL for NP0074309 (Woodfordin A)

3D SDF for NP0074309 (Woodfordin A)

3D-SDF for NP0074309 (Woodfordin A)

PDB for NP0074309 (Woodfordin A)

3D PDB for NP0074309 (Woodfordin A)

SMILES for NP0074309 (Woodfordin A)

INCHI for NP0074309 (Woodfordin A)

Structure for NP0074309 (Woodfordin A)

3D Structure for NP0074309 (Woodfordin A)