NP-MRD: Showing NP-Card for 3,4,5-trihydroxy-2-{[3,4,5,21,23-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(7),3,5,19,21-hexaen-22-yl]oxy}benzoic acid (NP0146366)

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Record Information

Version

2.0

Created at

2022-09-02 01:45:17 UTC

Updated at

2022-09-02 01:45:17 UTC

NP-MRD ID

NP0146366

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4,5-trihydroxy-2-{[3,4,5,21,23-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(7),3,5,19,21-hexaen-22-yl]oxy}benzoic acid

Description

Syzyginin A 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. Syzyginin A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, syzyginin a has been detected, but not quantified in, cloves and herbs and spices. 3,4,5-trihydroxy-2-{[3,4,5,21,23-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(7),3,5,19,21-hexaen-22-yl]oxy}benzoic acid is found in Syzygium aromaticum. This could make syzyginin a a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 09111213212D          

 79 86  0  0  0  0            999 V2000
    0.3659    0.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6217   -0.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3659   -1.7226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8611   -1.7226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8215   -0.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8611    0.2448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8215    0.0822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3659   -0.8977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6217   -1.5677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8611   -2.5476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9895    1.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9895    0.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2768    0.1480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9895   -1.9472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4670    1.4592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9959    2.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8190    0.1616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6957   -0.7001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3659    1.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1 69  1  0  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7 77  1  0  0  0  0
  8 66  1  0  0  0  0
  9 72  1  0  0  0  0
 10 75  1  0  0  0  0
 11 12  2  0  0  0  0
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 11 28  1  0  0  0  0
 12 13  1  0  0  0  0
 12 27  1  0  0  0  0
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 14 15  1  0  0  0  0
 14 70  1  0  0  0  0
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 16 26  1  0  0  0  0
 17 18  2  0  0  0  0
 17 22  1  0  0  0  0
 18 19  1  0  0  0  0
 18 72  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 25  1  0  0  0  0
 21 22  2  0  0  0  0
 21 24  1  0  0  0  0
 22 23  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 34  2  0  0  0  0
 30 31  2  0  0  0  0
 30 36  1  0  0  0  0
 31 32  1  0  0  0  0
 31 35  1  0  0  0  0
 32 33  2  0  0  0  0
 32 37  1  0  0  0  0
 33 34  1  0  0  0  0
 34 38  1  0  0  0  0
 38 67  2  0  0  0  0
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 39 40  1  0  0  0  0
 39 44  2  0  0  0  0
 40 41  2  0  0  0  0
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M  END

     RDKit          3D

113120  0  0  0  0  0  0  0  0999 V2000
   -5.2389   -3.6370    1.2959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0888   -3.0773    2.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0465   -2.1789    2.5315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1566   -1.8685    1.4458 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9557   -2.3664    1.7884 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8314   -1.6683    1.6848 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2977   -2.4304    0.9461 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4076   -1.7065    1.1468 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3576   -1.3038    1.9696 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3207   -1.1510    3.2614 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6842   -0.9503    1.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7480   -1.1131    2.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0609   -0.7937    2.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0802   -0.9772    2.9069 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3394   -0.2970    0.7410 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6437    0.0088    0.4577 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5069   -0.1989   -0.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1742   -1.3444   -0.8205 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.0683   -1.3802   -1.9044 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.4319    0.8430   -0.0911 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7244    0.1026   -3.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8037    0.2403   -4.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 09111213212D          

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M  END
> <DATABASE_ID>
NP0146366

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=C(OC2=C(O)C3=C(C=C2O)C(=O)OCC2OC(OC(=O)C4=CC(O)=C(O)C(O)=C4)C(OC(=O)C4=CC(O)=C(O)C(O)=C4)C(OC(=O)C4=CC(O)=C(O)C(O)=C4)C2OC(=O)C2=CC(O)=C(O)C(O)=C32)C(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C48H34O31/c49-17-1-11(2-18(50)29(17)58)43(68)77-40-39-26(74-48(79-45(70)13-5-21(53)31(60)22(54)6-13)41(40)78-44(69)12-3-19(51)30(59)20(52)4-12)10-73-46(71)14-8-25(57)38(75-37-16(42(66)67)9-24(56)33(62)36(37)65)35(64)28(14)27-15(47(72)76-39)7-23(55)32(61)34(27)63/h1-9,26,39-41,48-65H,10H2,(H,66,67)

> <INCHI_KEY>
HYXQWPAKDBAJLB-UHFFFAOYSA-N

> <FORMULA>
C48H34O31

> <MOLECULAR_WEIGHT>
1106.765

> <EXACT_MASS>
1106.10840437

> <JCHEM_ACCEPTOR_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
95.71197972561907

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
18

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4,5-trihydroxy-2-{[3,4,5,21,23-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(19),2,4,6,20,22-hexaen-22-yl]oxy}benzoic acid

> <ALOGPS_LOGP>
3.75

> <JCHEM_LOGP>
4.815199194

> <ALOGPS_LOGS>
-2.97

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
5.777588722921685

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4350719473271876

> <JCHEM_PKA_STRONGEST_BASIC>
-6.093258830151631

> <JCHEM_POLAR_SURFACE_AREA>
531.1700000000002

> <JCHEM_REFRACTIVITY>
251.28390000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.18e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-2-{[3,4,5,21,23-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(19),2,4,6,20,22-hexaen-22-yl]oxy}benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-12         0                                  
HETATM    1  C   UNK     0       0.683   0.457   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.161  -1.387   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.683  -3.216   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.474  -3.216   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.267  -1.387   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.474   0.457   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.267   0.153   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.683  -1.676   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.161  -2.926   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       3.474  -4.756   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -7.447   2.587   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.447   1.046   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.117   0.276   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.786   1.046   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.786   2.587   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.117   3.353   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.786  -3.635   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.786  -2.095   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.117  -1.325   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -7.447  -2.095   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -7.447  -3.635   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.117  -4.398   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.117  -5.938   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -8.781  -4.405   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -8.785  -1.325   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -6.117   4.893   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -8.785   0.276   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -8.781   3.356   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0     -10.321   3.356   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -11.095   4.687   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -12.642   4.687   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -13.412   3.356   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -12.642   2.015   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -11.095   2.015   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0     -13.412   6.024   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0     -10.325   6.024   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0     -14.952   3.356   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0     -10.632   0.862   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      11.098  -1.238   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      12.638  -1.238   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      13.408   0.092   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      12.638   1.422   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      11.098   1.422   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      10.336   0.092   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       7.957  -6.719   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       9.497  -6.719   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      10.267  -5.388   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       9.497  -4.061   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       7.957  -4.061   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       7.194  -5.388   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       7.895   4.061   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       9.435   4.061   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      10.205   5.392   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       9.435   6.719   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       7.895   6.719   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       7.132   5.392   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      10.267  -2.724   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      11.807  -5.388   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      10.267  -8.056   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      13.408  -2.572   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      14.952   0.092   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      13.408   2.760   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      10.205   8.056   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      11.745   5.392   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      10.205   2.724   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0       5.592   5.392   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0     -12.729   0.302   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0     -10.632  -1.307   0.000  0.00  0.00           O+0
HETATM   69  C   UNK     0       0.683   2.626   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      -3.004   1.542   0.000  0.00  0.00           C+0
HETATM   71  O   UNK     0      -3.004   3.711   0.000  0.00  0.00           O+0
HETATM   72  C   UNK     0      -2.689  -2.655   0.000  0.00  0.00           C+0
HETATM   73  O   UNK     0      -3.250  -4.752   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0      -1.124   2.626   0.000  0.00  0.00           O+0
HETATM   75  C   UNK     0       5.643  -4.756   0.000  0.00  0.00           C+0
HETATM   76  O   UNK     0       5.083  -6.852   0.000  0.00  0.00           O+0
HETATM   77  C   UNK     0       7.436   0.153   0.000  0.00  0.00           C+0
HETATM   78  O   UNK     0       7.436   2.323   0.000  0.00  0.00           O+0
HETATM   79  O   UNK     0       5.592   7.561   0.000  0.00  0.00           O+0
CONECT    1    2    6   69                                                  
CONECT    2    1    3    9                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    1    5                                                       
CONECT    7    5   77                                                       
CONECT    8    3   66                                                       
CONECT    9    2   72                                                       
CONECT   10    4   75                                                       
CONECT   11   12   16   28                                                  
CONECT   12   11   13   27                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15   70                                                  
CONECT   15   14   16                                                       
CONECT   16   11   15   26                                                  
CONECT   17   18   22                                                       
CONECT   18   17   19   72                                                  
CONECT   19   13   18   20                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   22   24                                                  
CONECT   22   17   21   23                                                  
CONECT   23   22                                                            
CONECT   24   21                                                            
CONECT   25   20                                                            
CONECT   26   16                                                            
CONECT   27   12                                                            
CONECT   28   11   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31   36                                                  
CONECT   31   30   32   35                                                  
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   29   33   38                                                  
CONECT   35   31                                                            
CONECT   36   30                                                            
CONECT   37   32                                                            
CONECT   38   34   67   68                                                  
CONECT   39   40   44                                                       
CONECT   40   39   41   60                                                  
CONECT   41   40   42   61                                                  
CONECT   42   41   43   62                                                  
CONECT   43   42   44                                                       
CONECT   44   39   43   77                                                  
CONECT   45   46   50                                                       
CONECT   46   45   47   59                                                  
CONECT   47   46   48   58                                                  
CONECT   48   47   49   57                                                  
CONECT   49   48   50                                                       
CONECT   50   45   49   75                                                  
CONECT   51   52   56                                                       
CONECT   52   51   53   65                                                  
CONECT   53   52   54   64                                                  
CONECT   54   53   55   63                                                  
CONECT   55   54   56                                                       
CONECT   56   51   55   66                                                  
CONECT   57   48                                                            
CONECT   58   47                                                            
CONECT   59   46                                                            
CONECT   60   40                                                            
CONECT   61   41                                                            
CONECT   62   42                                                            
CONECT   63   54                                                            
CONECT   64   53                                                            
CONECT   65   52                                                            
CONECT   66    8   56   79                                                  
CONECT   67   38                                                            
CONECT   68   38                                                            
CONECT   69    1   74                                                       
CONECT   70   14   71   74                                                  
CONECT   71   70                                                            
CONECT   72    9   18   73                                                  
CONECT   73   72                                                            
CONECT   74   69   70                                                       
CONECT   75   10   50   76                                                  
CONECT   76   75                                                            
CONECT   77    7   44   78                                                  
CONECT   78   77                                                            
CONECT   79   66                                                            
MASTER        0    0    0    0    0    0    0    0   79    0  172    0
END

View in JSmol

Synonyms

Value	Source
3,4,5-Trihydroxy-2-{[3,4,5,21,23-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-22-yl]oxy}benzoate	Generator

Chemical Formula

C₄₈H₃₄O₃₁

Average Mass

1106.7650 Da

Monoisotopic Mass

1106.10840 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

OC(=O)C1=C(OC2=C(O)C3=C(C=C2O)C(=O)OCC2OC(OC(=O)C4=CC(O)=C(O)C(O)=C4)C(OC(=O)C4=CC(O)=C(O)C(O)=C4)C(OC(=O)C4=CC(O)=C(O)C(O)=C4)C2OC(=O)C2=CC(O)=C(O)C(O)=C32)C(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C48H34O31/c49-17-1-11(2-18(50)29(17)58)43(68)77-40-39-26(74-48(79-45(70)13-5-21(53)31(60)22(54)6-13)41(40)78-44(69)12-3-19(51)30(59)20(52)4-12)10-73-46(71)14-8-25(57)38(75-37-16(42(66)67)9-24(56)33(62)36(37)65)35(64)28(14)27-15(47(72)76-39)7-23(55)32(61)34(27)63/h1-9,26,39-41,48-65H,10H2,(H,66,67)

InChI Key

HYXQWPAKDBAJLB-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Syzygium aromaticum	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
Hexacarboxylic acid or derivatives
Galloyl ester
Gallic acid or derivatives
Gallic acid
Diaryl ether
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Hydroxybenzoic acid
Benzoate ester
Benzenetriol
Pyrogallol derivative
Benzoic acid or derivatives
Benzoic acid
Benzoyl
Phenol ether
Phenoxy compound
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Carboxylic acid ester
Lactone
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Ether
Carboxylic acid
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.75	ALOGPS
logP	4.82	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.44	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	25	ChemAxon
Hydrogen Donor Count	18	ChemAxon
Polar Surface Area	531.17 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	251.28 m³·mol⁻¹	ChemAxon
Polarizability	95.71 Å³	ChemAxon
Number of Rings	8	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

HMDB0030236

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002059

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

131750984

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4,5-trihydroxy-2-{[3,4,5,21,23-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(7),3,5,19,21-hexaen-22-yl]oxy}benzoic acid (NP0146366)

MOL for NP0146366 (3,4,5-trihydroxy-2-{[3,4,5,21,23-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(7),3,5,19,21-hexaen-22-yl]oxy}benzoic acid)

3D MOL for NP0146366 (3,4,5-trihydroxy-2-{[3,4,5,21,23-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(7),3,5,19,21-hexaen-22-yl]oxy}benzoic acid)

3D SDF for NP0146366 (3,4,5-trihydroxy-2-{[3,4,5,21,23-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(7),3,5,19,21-hexaen-22-yl]oxy}benzoic acid)

3D-SDF for NP0146366 (3,4,5-trihydroxy-2-{[3,4,5,21,23-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(7),3,5,19,21-hexaen-22-yl]oxy}benzoic acid)

PDB for NP0146366 (3,4,5-trihydroxy-2-{[3,4,5,21,23-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(7),3,5,19,21-hexaen-22-yl]oxy}benzoic acid)

3D PDB for NP0146366 (3,4,5-trihydroxy-2-{[3,4,5,21,23-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(7),3,5,19,21-hexaen-22-yl]oxy}benzoic acid)

SMILES for NP0146366 (3,4,5-trihydroxy-2-{[3,4,5,21,23-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(7),3,5,19,21-hexaen-22-yl]oxy}benzoic acid)

INCHI for NP0146366 (3,4,5-trihydroxy-2-{[3,4,5,21,23-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(7),3,5,19,21-hexaen-22-yl]oxy}benzoic acid)

Structure for NP0146366 (3,4,5-trihydroxy-2-{[3,4,5,21,23-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(7),3,5,19,21-hexaen-22-yl]oxy}benzoic acid)

3D Structure for NP0146366 (3,4,5-trihydroxy-2-{[3,4,5,21,23-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(7),3,5,19,21-hexaen-22-yl]oxy}benzoic acid)