NP-MRD: Showing NP-Card for Paeonianin D (NP0080049)

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Record Information

Version

2.0

Created at

2022-04-29 01:06:27 UTC

Updated at

2022-04-29 01:06:27 UTC

NP-MRD ID

NP0080049

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Paeonianin D

Description

[(2S,3R,4S,5R,6S)-3,4,5,6-tetrakis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]methyl 2-[(14R,15R,19S)-14-[(10S,11S)-3,4,5,11,17,18,19-heptahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.4.0.0²,⁷]Nonadeca-1(19),2,4,6,15,17-hexaen-10-yl]-2,3,4,7,8,9-hexahydroxy-12,17-dioxo-13,16-dioxatetracyclo[13.3.1.0⁵,¹⁸.0⁶,¹¹]Nonadeca-1,3,5(18),6,8,10-hexaen-19-yl]-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. Paeonianin D is found in Paeonia albiflora . Based on a literature review very few articles have been published on [(2S,3R,4S,5R,6S)-3,4,5,6-tetrakis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]methyl 2-[(14R,15R,19S)-14-[(10S,11S)-3,4,5,11,17,18,19-heptahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.4.0.0²,⁷]Nonadeca-1(19),2,4,6,15,17-hexaen-10-yl]-2,3,4,7,8,9-hexahydroxy-12,17-dioxo-13,16-dioxatetracyclo[13.3.1.0⁵,¹⁸.0⁶,¹¹]Nonadeca-1,3,5(18),6,8,10-hexaen-19-yl]-3,4,5-trihydroxybenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292203062D          

122134  0  0  1  0            999 V2000
    7.1854    2.3893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5077    3.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0112    3.8076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1923    3.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8700    2.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3666    2.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0351    1.4039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1334    2.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2438    2.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2419    2.8389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4383    2.4881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9037    3.6208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6959    3.9514    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1211    4.6879    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.0828    1.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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M  END

     RDKit          3D

176188  0  0  0  0  0  0  0  0999 V2000
   -3.7496   -1.4841    1.7788 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304292203062D          

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M  END
> <DATABASE_ID>
NP0080049

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1COC(=O)C2=C(C(O)=C(O)C(O)=C2)C2=C(C=C(O)C(O)=C2O)C(=O)O[C@@H]1[C@@H]1OC(=O)C2=CC(O)=C(O)C(O)=C2C2=C3C(=O)O[C@@H]1[C@@H](C1=C(C=C(O)C(O)=C1O)C(=O)OC[C@@H]1O[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](OC(=O)C4=CC(O)=C(O)C(O)=C4)[C@@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1)C3=C(O)C(O)=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C75H54O47/c76-23-1-15(2-24(77)45(23)89)66(104)117-61-36(115-75(122-69(107)18-7-29(82)48(92)30(83)8-18)65(121-68(106)17-5-27(80)47(91)28(81)6-17)64(61)119-67(105)16-3-25(78)46(90)26(79)4-16)14-114-71(109)20-10-32(85)52(96)56(100)40(20)43-42-44-41(57(101)59(103)58(42)102)39-22(12-34(87)51(95)55(39)99)73(111)120-63(62(43)118-74(44)112)60-35(88)13-113-70(108)19-9-31(84)49(93)53(97)37(19)38-21(72(110)116-60)11-33(86)50(94)54(38)98/h1-12,35-36,43,60-65,75-103H,13-14H2/t35-,36-,43-,60-,61+,62+,63-,64-,65+,75-/m0/s1

> <INCHI_KEY>
IADPIYNHCXUODW-ZIJIKNGASA-N

> <FORMULA>
C75H54O47

> <MOLECULAR_WEIGHT>
1707.21

> <EXACT_MASS>
1706.183538879

> <JCHEM_ACCEPTOR_COUNT>
38

> <JCHEM_ATOM_COUNT>
176

> <JCHEM_AVERAGE_POLARIZABILITY>
150.85746586241356

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
28

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S,3R,4S,5R,6S)-3,4,5,6-tetrakis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]methyl 2-[(14R,15R,19S)-14-[(10S,11S)-3,4,5,11,17,18,19-heptahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.4.0.0^{2,7}]nonadeca-1(15),2(7),3,5,16,18-hexaen-10-yl]-2,3,4,7,8,9-hexahydroxy-12,17-dioxo-13,16-dioxatetracyclo[13.3.1.0^{5,18}.0^{6,11}]nonadeca-1,3,5(18),6,8,10-hexaen-19-yl]-3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
3.89

> <JCHEM_LOGP>
6.402357479666665

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
13

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.671981527961034

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.2331020933733665

> <JCHEM_PKA_STRONGEST_BASIC>
-6.173381853540886

> <JCHEM_POLAR_SURFACE_AREA>
812.3700000000005

> <JCHEM_REFRACTIVITY>
389.8915999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.83e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,3R,4S,5R,6S)-3,4,5,6-tetrakis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]methyl 2-[(14R,15R,19S)-14-[(10S,11S)-3,4,5,11,17,18,19-heptahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.4.0.0^{2,7}]nonadeca-1(15),2(7),3,5,16,18-hexaen-10-yl]-2,3,4,7,8,9-hexahydroxy-12,17-dioxo-13,16-dioxatetracyclo[13.3.1.0^{5,18}.0^{6,11}]nonadeca-1,3,5(18),6,8,10-hexaen-19-yl]-3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      13.413   4.460   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.014   5.878   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.087   7.108   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.559   6.920   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.957   5.502   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.884   4.272   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.265   2.621   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.582   4.841   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.922   4.932   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.051   5.299   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.552   4.645   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.420   6.759   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.899   7.376   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.693   8.751   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.307   9.074   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.788   8.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.672   9.739   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.795  10.002   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.523  11.522   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.920  12.170   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.734  13.699   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.223  13.996   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.863  12.643   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.154  15.298   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.625  15.113   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.021  13.696   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.206  12.168   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.945  12.465   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.216  13.718   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.266   9.817   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.974  11.243   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.558  11.847   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.373  13.376   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.604  14.300   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.444  15.823   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -0.171  13.791   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.277  10.888   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.700  16.344   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.304  17.761   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.833  17.946   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       6.758  16.715   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       6.568  19.369   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       3.845  19.316   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       1.883  16.709   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       6.135  12.062   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       6.996   5.748   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       6.799   4.026   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       7.621   2.619   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       9.183   2.262   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      10.422   3.284   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      11.965   2.003   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       8.455   0.652   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       6.744   1.147   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       8.535   5.706   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       9.269   4.352   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       8.453   2.894   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       9.450   1.264   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0       6.601   2.596   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0       6.053   1.157   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       4.533   0.912   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       3.984  -0.527   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       2.464  -0.772   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       1.492   0.422   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0       2.040   1.861   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0       1.068   3.056   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      -0.453   2.811   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      -1.001   1.372   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      -1.425   4.005   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      -2.945   3.760   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      -3.918   4.955   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      -3.370   6.394   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      -1.849   6.639   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      -0.877   5.444   0.000  0.00  0.00           C+0
HETATM   74  O   UNK     0      -1.301   8.078   0.000  0.00  0.00           O+0
HETATM   75  O   UNK     0      -4.342   7.588   0.000  0.00  0.00           O+0
HETATM   76  O   UNK     0      -5.438   4.710   0.000  0.00  0.00           O+0
HETATM   77  O   UNK     0       3.560   2.106   0.000  0.00  0.00           O+0
HETATM   78  O   UNK     0      -0.029   0.177   0.000  0.00  0.00           O+0
HETATM   79  C   UNK     0      -0.669  -1.909   0.000  0.00  0.00           C+0
HETATM   80  O   UNK     0       0.303  -3.103   0.000  0.00  0.00           O+0
HETATM   81  C   UNK     0      -2.097  -1.507   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0      -2.645  -2.946   0.000  0.00  0.00           C+0
HETATM   83  C   UNK     0      -4.166  -3.191   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0      -5.138  -1.996   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0      -4.590  -0.557   0.000  0.00  0.00           C+0
HETATM   86  C   UNK     0      -3.069  -0.312   0.000  0.00  0.00           C+0
HETATM   87  O   UNK     0      -5.562   0.637   0.000  0.00  0.00           O+0
HETATM   88  O   UNK     0      -6.658  -2.241   0.000  0.00  0.00           O+0
HETATM   89  O   UNK     0      -4.714  -4.630   0.000  0.00  0.00           O+0
HETATM   90  O   UNK     0       1.916  -2.211   0.000  0.00  0.00           O+0
HETATM   91  C   UNK     0       0.395  -2.456   0.000  0.00  0.00           C+0
HETATM   92  O   UNK     0      -0.577  -1.262   0.000  0.00  0.00           O+0
HETATM   93  C   UNK     0      -0.153  -3.895   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0       0.820  -5.089   0.000  0.00  0.00           C+0
HETATM   95  C   UNK     0       0.271  -6.529   0.000  0.00  0.00           C+0
HETATM   96  C   UNK     0      -1.249  -6.773   0.000  0.00  0.00           C+0
HETATM   97  C   UNK     0      -2.221  -5.579   0.000  0.00  0.00           C+0
HETATM   98  C   UNK     0      -1.673  -4.140   0.000  0.00  0.00           C+0
HETATM   99  O   UNK     0      -3.742  -5.824   0.000  0.00  0.00           O+0
HETATM  100  O   UNK     0      -1.797  -8.213   0.000  0.00  0.00           O+0
HETATM  101  O   UNK     0       1.244  -7.723   0.000  0.00  0.00           O+0
HETATM  102  O   UNK     0       4.957  -1.721   0.000  0.00  0.00           O+0
HETATM  103  C   UNK     0       4.409  -3.161   0.000  0.00  0.00           C+0
HETATM  104  O   UNK     0       2.888  -3.405   0.000  0.00  0.00           O+0
HETATM  105  C   UNK     0       5.381  -4.355   0.000  0.00  0.00           C+0
HETATM  106  C   UNK     0       6.901  -4.110   0.000  0.00  0.00           C+0
HETATM  107  C   UNK     0       7.873  -5.304   0.000  0.00  0.00           C+0
HETATM  108  C   UNK     0       7.325  -6.743   0.000  0.00  0.00           C+0
HETATM  109  C   UNK     0       5.805  -6.988   0.000  0.00  0.00           C+0
HETATM  110  C   UNK     0       4.833  -5.794   0.000  0.00  0.00           C+0
HETATM  111  O   UNK     0       5.257  -8.427   0.000  0.00  0.00           O+0
HETATM  112  O   UNK     0       8.298  -7.938   0.000  0.00  0.00           O+0
HETATM  113  O   UNK     0       9.394  -5.059   0.000  0.00  0.00           O+0
HETATM  114  C   UNK     0      10.808   4.310   0.000  0.00  0.00           C+0
HETATM  115  C   UNK     0      11.614   5.622   0.000  0.00  0.00           C+0
HETATM  116  C   UNK     0      10.881   6.976   0.000  0.00  0.00           C+0
HETATM  117  C   UNK     0       9.341   7.018   0.000  0.00  0.00           C+0
HETATM  118  O   UNK     0       8.484   8.109   0.000  0.00  0.00           O+0
HETATM  119  O   UNK     0      12.179   8.239   0.000  0.00  0.00           O+0
HETATM  120  O   UNK     0      13.168   5.479   0.000  0.00  0.00           O+0
HETATM  121  O   UNK     0      15.571   6.532   0.000  0.00  0.00           O+0
HETATM  122  O   UNK     0      14.728   3.340   0.000  0.00  0.00           O+0
CONECT    1    2    6  122                                                  
CONECT    2    1    3  121                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   50                                                  
CONECT    9    8   10   47                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   46                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15    4   17                                                  
CONECT   17   16                                                            
CONECT   18   14   19   30                                                  
CONECT   19   18   20   45                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   41                                                  
CONECT   25   24   26   38                                                  
CONECT   26   25   27   34                                                  
CONECT   27   26   28   31                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   18                                                       
CONECT   31   27   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34   36                                                  
CONECT   34   33   26   35                                                  
CONECT   35   34                                                            
CONECT   36   33                                                            
CONECT   37   32                                                            
CONECT   38   25   39   44                                                  
CONECT   39   38   40   43                                                  
CONECT   40   39   41   42                                                  
CONECT   41   40   24                                                       
CONECT   42   40                                                            
CONECT   43   39                                                            
CONECT   44   38                                                            
CONECT   45   19                                                            
CONECT   46   13   47   54                                                  
CONECT   47   46    9   48                                                  
CONECT   48   47   49   53                                                  
CONECT   49   48   50   52                                                  
CONECT   50   49    8   51                                                  
CONECT   51   50                                                            
CONECT   52   49                                                            
CONECT   53   48                                                            
CONECT   54   46   55  117                                                  
CONECT   55   54   56  114                                                  
CONECT   56   55   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61   77                                                  
CONECT   61   60   62  102                                                  
CONECT   62   61   63   90                                                  
CONECT   63   62   64   78                                                  
CONECT   64   63   65   77                                                  
CONECT   65   64   66                                                       
CONECT   66   65   67   68                                                  
CONECT   67   66                                                            
CONECT   68   66   69   73                                                  
CONECT   69   68   70                                                       
CONECT   70   69   71   76                                                  
CONECT   71   70   72   75                                                  
CONECT   72   71   73   74                                                  
CONECT   73   72   68                                                       
CONECT   74   72                                                            
CONECT   75   71                                                            
CONECT   76   70                                                            
CONECT   77   64   60                                                       
CONECT   78   63   79                                                       
CONECT   79   78   80   81                                                  
CONECT   80   79                                                            
CONECT   81   79   82   86                                                  
CONECT   82   81   83                                                       
CONECT   83   82   84   89                                                  
CONECT   84   83   85   88                                                  
CONECT   85   84   86   87                                                  
CONECT   86   85   81                                                       
CONECT   87   85                                                            
CONECT   88   84                                                            
CONECT   89   83                                                            
CONECT   90   62   91                                                       
CONECT   91   90   92   93                                                  
CONECT   92   91                                                            
CONECT   93   91   94   98                                                  
CONECT   94   93   95                                                       
CONECT   95   94   96  101                                                  
CONECT   96   95   97  100                                                  
CONECT   97   96   98   99                                                  
CONECT   98   97   93                                                       
CONECT   99   97                                                            
CONECT  100   96                                                            
CONECT  101   95                                                            
CONECT  102   61  103                                                       
CONECT  103  102  104  105                                                  
CONECT  104  103                                                            
CONECT  105  103  106  110                                                  
CONECT  106  105  107                                                       
CONECT  107  106  108  113                                                  
CONECT  108  107  109  112                                                  
CONECT  109  108  110  111                                                  
CONECT  110  109  105                                                       
CONECT  111  109                                                            
CONECT  112  108                                                            
CONECT  113  107                                                            
CONECT  114   55  115                                                       
CONECT  115  114  116  120                                                  
CONECT  116  115  117  119                                                  
CONECT  117  116   54  118                                                  
CONECT  118  117                                                            
CONECT  119  116                                                            
CONECT  120  115                                                            
CONECT  121    2                                                            
CONECT  122    1                                                            
MASTER        0    0    0    0    0    0    0    0  122    0  268    0
END

View in JSmol

Synonyms

Value	Source
[(2S,3R,4S,5R,6S)-3,4,5,6-Tetrakis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]methyl 2-[(14R,15R,19S)-14-[(10S,11S)-3,4,5,11,17,18,19-heptahydroxy-8,14-dioxo-9,13-dioxatricyclo[13.4.0.0,]nonadeca-1(19),2,4,6,15,17-hexaen-10-yl]-2,3,4,7,8,9-hexahydroxy-12,17-dioxo-13,16-dioxatetracyclo[13.3.1.0,.0,]nonadeca-1,3,5(18),6,8,10-hexaen-19-yl]-3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₇₅H₅₄O₄₇

Average Mass

1707.2100 Da

Monoisotopic Mass

1706.18354 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

O[C@H]1COC(=O)C2=C(C(O)=C(O)C(O)=C2)C2=C(C=C(O)C(O)=C2O)C(=O)O[C@@H]1[C@@H]1OC(=O)C2=CC(O)=C(O)C(O)=C2C2=C3C(=O)O[C@@H]1[C@@H](C1=C(C=C(O)C(O)=C1O)C(=O)OC[C@@H]1O[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](OC(=O)C4=CC(O)=C(O)C(O)=C4)[C@@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1)C3=C(O)C(O)=C2O

InChI Identifier

InChI=1S/C75H54O47/c76-23-1-15(2-24(77)45(23)89)66(104)117-61-36(115-75(122-69(107)18-7-29(82)48(92)30(83)8-18)65(121-68(106)17-5-27(80)47(91)28(81)6-17)64(61)119-67(105)16-3-25(78)46(90)26(79)4-16)14-114-71(109)20-10-32(85)52(96)56(100)40(20)43-42-44-41(57(101)59(103)58(42)102)39-22(12-34(87)51(95)55(39)99)73(111)120-63(62(43)118-74(44)112)60-35(88)13-113-70(108)19-9-31(84)49(93)53(97)37(19)38-21(72(110)116-60)11-33(86)50(94)54(38)98/h1-12,35-36,43,60-65,75-103H,13-14H2/t35-,36-,43-,60-,61+,62+,63-,64-,65+,75-/m0/s1

InChI Key

IADPIYNHCXUODW-ZIJIKNGASA-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
Paeonia lactiflora	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
2-benzopyran
Isochromane
Benzopyran
Benzoate ester
Pyrogallol derivative
Benzoic acid or derivatives
Benzenetriol
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
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	3.89	ALOGPS
logP	6.4	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	7.23	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	38	ChemAxon
Hydrogen Donor Count	28	ChemAxon
Polar Surface Area	812.37 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	389.89 m³·mol⁻¹	ChemAxon
Polarizability	150.86 Å³	ChemAxon
Number of Rings	13	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

162972921

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Paeonianin D (NP0080049)

MOL for NP0080049 (Paeonianin D)

3D MOL for NP0080049 (Paeonianin D)

3D SDF for NP0080049 (Paeonianin D)

3D-SDF for NP0080049 (Paeonianin D)

PDB for NP0080049 (Paeonianin D)

3D PDB for NP0080049 (Paeonianin D)

SMILES for NP0080049 (Paeonianin D)

INCHI for NP0080049 (Paeonianin D)

Structure for NP0080049 (Paeonianin D)

3D Structure for NP0080049 (Paeonianin D)