NP-MRD: Showing NP-Card for Geraniinic acid C (NP0074256)

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Record Information

Version

2.0

Created at

2022-04-28 19:24:42 UTC

Updated at

2022-04-28 19:24:42 UTC

NP-MRD ID

NP0074256

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Geraniinic acid C

Description

(1R,3S,4R,13R,14S,21R,22S)-9,10,11,27,28,29,32,33,34-nonahydroxy-6,16,19,24,37-pentaoxo-3-(3,4,5-trihydroxybenzoyloxy)-2,5,15,20,23,38-hexaoxaheptacyclo[19.18.0.0⁴,²².0⁷,¹².0¹³,¹⁸.0²⁵,³⁰.0³¹,³⁶]Nonatriaconta-7,9,11,17,25,27,29,31,33,35-decaene-14-carboxylic acid 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. Geraniinic acid C is found in Geranium thunbergii. Based on a literature review very few articles have been published on (1R,3S,4R,13R,14S,21R,22S)-9,10,11,27,28,29,32,33,34-nonahydroxy-6,16,19,24,37-pentaoxo-3-(3,4,5-trihydroxybenzoyloxy)-2,5,15,20,23,38-hexaoxaheptacyclo[19.18.0.0⁴,²².0⁷,¹².0¹³,¹⁸.0²⁵,³⁰.0³¹,³⁶]Nonatriaconta-7,9,11,17,25,27,29,31,33,35-decaene-14-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221242D          

 68 75  0  0  1  0            999 V2000
    0.2123   -0.9395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0178   -1.1181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5752   -0.5099    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3272    0.2770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1950    0.7235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5288    1.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3826    1.8637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5575    2.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5258    1.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3989    1.0759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3587    0.2719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8780    1.7476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4280    2.7052    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1819    2.6311    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5014    2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5086    1.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0891    0.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0354    0.6374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411    0.0260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0357   -0.1526    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5217    0.4556    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2737    1.2424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7772    1.7471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2704    2.5603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6958    1.7859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2814    2.3670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9994    2.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2474    1.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6900    0.7066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2787    1.3068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9380   -0.0803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3806   -0.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0528    1.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6102    1.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3622    2.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5568    2.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4546    3.5827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0223    3.0827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4528    1.5818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0708    3.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2748    3.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6892    2.8001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8997    2.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5237    3.7918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4613    4.2555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7282    3.7955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2267    1.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9375    1.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9303    2.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2122    2.7480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7714    3.4432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7659    2.6105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8305    1.4131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0683    3.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8503    4.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0021    3.9811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1360   -1.7686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133   -2.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9176   -2.7617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4480   -3.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2051   -3.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7665   -4.5754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5707   -4.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8136   -3.6031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2523   -2.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6179   -3.4193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1321   -4.9961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5236   -5.3639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14  8  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 20 19  1  6  0  0  0
  1 20  1  0  0  0  0
 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
  3 32  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 27 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 38  1  0  0  0  0
 34 39  1  0  0  0  0
 26 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 25 43  1  0  0  0  0
 42 44  1  0  0  0  0
 41 45  1  0  0  0  0
 40 46  1  0  0  0  0
 16 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 15 50  1  0  0  0  0
 50 51  1  0  0  0  0
 49 52  1  0  0  0  0
 48 53  1  0  0  0  0
 13 54  1  6  0  0  0
 54 55  2  0  0  0  0
 54 56  1  0  0  0  0
  1 57  1  1  0  0  0
 57 58  1  0  0  0  0
 58 59  2  0  0  0  0
 58 60  1  0  0  0  0
 60 61  2  0  0  0  0
 61 62  1  0  0  0  0
 62 63  2  0  0  0  0
 63 64  1  0  0  0  0
 64 65  2  0  0  0  0
 60 65  1  0  0  0  0
 64 66  1  0  0  0  0
 63 67  1  0  0  0  0
 62 68  1  0  0  0  0
M  END

     RDKit          3D

 96103  0  0  0  0  0  0  0  0999 V2000
   -2.6647   -5.9960   -1.2883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4701   -4.7920   -0.9971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3025   -4.1411   -0.4966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1703   -2.7985   -0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1197   -2.5119    0.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4291   -3.2852    1.4407 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1146   -1.6104    0.2138 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0769   -0.3921   -0.2599 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5445    0.5539    0.8548 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6128    0.0304    2.0643 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2516    0.2317    3.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3577    0.5990    4.1745 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6484    0.1609    3.7051 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0594    1.2899    4.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2382    1.4035    5.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5519    2.6001    5.7643 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9781    0.2476    5.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1999    0.2526    5.9544 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6424   -0.9137    4.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4738   -1.9827    4.7220 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4405   -0.9681    3.7761 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3676   -2.2585    3.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5760   -2.6400    1.6973 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4050   -3.9944    1.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0366   -4.9805    2.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8640   -6.3088    1.8858 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8488   -4.5956    3.5816 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4845   -5.5199    4.5744 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0143   -3.2816    3.9198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7974   -2.9919    5.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1060   -1.7862    0.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3091   -2.2924    0.3216 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8226   -0.7504   -0.0921 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2932   -0.1879   -1.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0655    0.4973   -0.8106 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3722    1.4172   -1.5641 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3536    2.1136   -0.8884 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5087    2.7082   -1.7896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798    3.9461   -1.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4908    4.6513   -0.7309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8230    4.7662   -2.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2374    6.0336   -2.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0069    6.8238   -3.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4279    8.0930   -2.6540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3939    6.3819   -4.2668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1835    7.2180   -5.0793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0115    5.1414   -4.7019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4394    4.7575   -5.9811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2444    4.3594   -3.8834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4737    1.1636    0.0345 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6930    1.4681    0.4684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8273    1.1811   -0.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9183    1.7676   -0.0631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8573    0.2969   -1.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1767    0.9565   -2.7268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1676    0.3716   -3.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4982    1.0908   -5.1169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8301   -0.9301   -4.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7892   -1.6113   -5.2711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5104   -1.6267   -2.8597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660   -2.9540   -3.0463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5140   -1.0734   -1.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3303   -1.9492   -0.4300 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5909   -2.8425   -0.3110 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8210   -2.1162   -0.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5615   -2.3490   -1.5089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3721   -1.1171    0.3466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5878   -3.9232   -1.2016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4622   -4.8491   -0.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2796   -0.5449   -1.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3176    1.4374    0.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4611    2.2285    4.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3895    2.7277    6.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4956    1.0842    6.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2904   -2.1223    5.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5828   -4.3780    0.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5655   -6.9684    2.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3379   -6.5033    4.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5608   -3.6868    5.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0386    0.4781   -1.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0057   -0.9436   -2.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5346    1.2554   -0.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
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  9 71  1  1
  8 70  1  6
M  END


  Mrv1652304282221242D          

 68 75  0  0  1  0            999 V2000
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   -2.8305    1.4131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0683    3.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8503    4.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9176   -2.7617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 40 46  1  0  0  0  0
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 54 55  2  0  0  0  0
 54 56  1  0  0  0  0
  1 57  1  1  0  0  0
 57 58  1  0  0  0  0
 58 59  2  0  0  0  0
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 63 64  1  0  0  0  0
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 64 66  1  0  0  0  0
 63 67  1  0  0  0  0
 62 68  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074256

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)[C@H]1OC(=O)C=C2[C@H]1C1=C(C=C(O)C(O)=C1O)C(=O)O[C@H]1[C@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)O[C@@H]3COC(=O)C4=C(C(O)=C(O)C(O)=C4)C4=C(C=C(O)C(O)=C4O)C(=O)O[C@H]1[C@@H]3OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C41H28O27/c42-13-1-8(2-14(43)24(13)48)36(57)68-41-34-33-31(65-40(61)12-6-19(47)64-32(35(55)56)23(12)22-11(39(60)67-34)5-17(46)27(51)30(22)54)18(63-41)7-62-37(58)9-3-15(44)25(49)28(52)20(9)21-10(38(59)66-33)4-16(45)26(50)29(21)53/h1-6,18,23,31-34,41-46,48-54H,7H2,(H,55,56)/t18-,23+,31-,32+,33+,34-,41+/m1/s1

> <INCHI_KEY>
WYUXUOKOWFMOCI-RQXCGLAYSA-N

> <FORMULA>
C41H28O27

> <MOLECULAR_WEIGHT>
952.648

> <EXACT_MASS>
952.081795642

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
83.39125257199629

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3S,4R,13R,14S,21R,22S)-9,10,11,27,28,29,32,33,34-nonahydroxy-6,16,19,24,37-pentaoxo-3-(3,4,5-trihydroxybenzoyloxy)-2,5,15,20,23,38-hexaoxaheptacyclo[19.18.0.0^{4,22}.0^{7,12}.0^{13,18}.0^{25,30}.0^{31,36}]nonatriaconta-7(12),8,10,17,25(30),26,28,31(36),32,34-decaene-14-carboxylic acid

> <ALOGPS_LOGP>
3.32

> <JCHEM_LOGP>
2.8534615639999994

> <ALOGPS_LOGS>
-2.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
7.335526734102301

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7232759233642088

> <JCHEM_PKA_STRONGEST_BASIC>
-6.112241185381145

> <JCHEM_POLAR_SURFACE_AREA>
447.0900000000001

> <JCHEM_REFRACTIVITY>
210.90830000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.79e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,4R,13R,14S,21R,22S)-9,10,11,27,28,29,32,33,34-nonahydroxy-6,16,19,24,37-pentaoxo-3-(3,4,5-trihydroxybenzoyloxy)-2,5,15,20,23,38-hexaoxaheptacyclo[19.18.0.0^{4,22}.0^{7,12}.0^{13,18}.0^{25,30}.0^{31,36}]nonatriaconta-7(12),8,10,17,25(30),26,28,31(36),32,34-decaene-14-carboxylic acid

> <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       0.396  -1.754   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.900  -2.087   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.940  -0.952   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.477   0.517   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.097   1.351   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.854   2.735   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.448   3.479   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.041   3.758   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.981   2.055   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.745   2.008   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.670   0.508   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.639   3.262   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.799   5.050   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.340   4.911   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.936   4.348   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.949   2.808   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.033   1.517   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.799   1.190   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.570   0.049   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.067  -0.285   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.974   0.850   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.511   2.319   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.451   3.261   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.371   4.779   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.165   3.334   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.259   4.418   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.599   3.923   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.062   2.454   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.021   1.319   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.254   2.439   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       5.484  -0.150   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.444  -1.285   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.565   2.121   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.606   3.256   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.143   4.725   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.639   5.058   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       6.449   6.688   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       9.375   5.754   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      10.179   2.953   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       3.866   5.907   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.380   6.312   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.287   5.227   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.679   3.738   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       0.978   7.078   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       2.728   7.944   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       5.093   7.085   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -2.290   2.050   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -3.617   2.831   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -3.603   4.371   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -2.263   5.130   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -3.307   6.427   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      -5.163   4.873   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      -5.284   2.638   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      -1.994   6.655   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      -1.587   8.267   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      -3.737   7.431   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      -0.254  -3.301   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       0.212  -4.812   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0       1.713  -5.155   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      -0.836  -5.941   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      -0.383  -7.412   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      -1.431  -8.541   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      -2.932  -8.198   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      -3.385  -6.726   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      -2.338  -5.597   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0      -4.887  -6.383   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0      -3.980  -9.326   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0      -0.977 -10.013   0.000  0.00  0.00           O+0
CONECT    1    2   20   57                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   54                                                  
CONECT   14   13    8   15                                                  
CONECT   15   14   16   50                                                  
CONECT   16   15   17   47                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19    1   21                                                  
CONECT   21   20    4   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   43                                                  
CONECT   26   25   27   40                                                  
CONECT   27   26   28   36                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31    3                                                       
CONECT   33   28   34                                                       
CONECT   34   33   35   39                                                  
CONECT   35   34   36   38                                                  
CONECT   36   35   27   37                                                  
CONECT   37   36                                                            
CONECT   38   35                                                            
CONECT   39   34                                                            
CONECT   40   26   41   46                                                  
CONECT   41   40   42   45                                                  
CONECT   42   41   43   44                                                  
CONECT   43   42   25                                                       
CONECT   44   42                                                            
CONECT   45   41                                                            
CONECT   46   40                                                            
CONECT   47   16   48                                                       
CONECT   48   47   49   53                                                  
CONECT   49   48   50   52                                                  
CONECT   50   49   15   51                                                  
CONECT   51   50                                                            
CONECT   52   49                                                            
CONECT   53   48                                                            
CONECT   54   13   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54                                                            
CONECT   57    1   58                                                       
CONECT   58   57   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58   61   65                                                  
CONECT   61   60   62                                                       
CONECT   62   61   63   68                                                  
CONECT   63   62   64   67                                                  
CONECT   64   63   65   66                                                  
CONECT   65   64   60                                                       
CONECT   66   64                                                            
CONECT   67   63                                                            
CONECT   68   62                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  150    0
END

View in JSmol

Synonyms

Value	Source
(1R,3S,4R,13R,14S,21R,22S)-9,10,11,27,28,29,32,33,34-Nonahydroxy-6,16,19,24,37-pentaoxo-3-(3,4,5-trihydroxybenzoyloxy)-2,5,15,20,23,38-hexaoxaheptacyclo[19.18.0.0,.0,.0,.0,.0,]nonatriaconta-7,9,11,17,25,27,29,31,33,35-decaene-14-carboxylate	Generator

Chemical Formula

C₄₁H₂₈O₂₇

Average Mass

952.6480 Da

Monoisotopic Mass

952.08180 Da

IUPAC Name

(1R,3S,4R,13R,14S,21R,22S)-9,10,11,27,28,29,32,33,34-nonahydroxy-6,16,19,24,37-pentaoxo-3-(3,4,5-trihydroxybenzoyloxy)-2,5,15,20,23,38-hexaoxaheptacyclo[19.18.0.0^{4,22}.0^{7,12}.0^{13,18}.0^{25,30}.0^{31,36}]nonatriaconta-7(12),8,10,17,25(30),26,28,31(36),32,34-decaene-14-carboxylic acid

Traditional Name

(1R,3S,4R,13R,14S,21R,22S)-9,10,11,27,28,29,32,33,34-nonahydroxy-6,16,19,24,37-pentaoxo-3-(3,4,5-trihydroxybenzoyloxy)-2,5,15,20,23,38-hexaoxaheptacyclo[19.18.0.0^{4,22}.0^{7,12}.0^{13,18}.0^{25,30}.0^{31,36}]nonatriaconta-7(12),8,10,17,25(30),26,28,31(36),32,34-decaene-14-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)[C@H]1OC(=O)C=C2[C@H]1C1=C(C=C(O)C(O)=C1O)C(=O)O[C@H]1[C@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)O[C@@H]3COC(=O)C4=C(C(O)=C(O)C(O)=C4)C4=C(C=C(O)C(O)=C4O)C(=O)O[C@H]1[C@@H]3OC2=O

InChI Identifier

InChI=1S/C41H28O27/c42-13-1-8(2-14(43)24(13)48)36(57)68-41-34-33-31(65-40(61)12-6-19(47)64-32(35(55)56)23(12)22-11(39(60)67-34)5-17(46)27(51)30(22)54)18(63-41)7-62-37(58)9-3-15(44)25(49)28(52)20(9)21-10(38(59)66-33)4-16(45)26(50)29(21)53/h1-6,18,23,31-34,41-46,48-54H,7H2,(H,55,56)/t18-,23+,31-,32+,33+,34-,41+/m1/s1

InChI Key

WYUXUOKOWFMOCI-RQXCGLAYSA-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
Geranium thunbergii	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
Saccharolipid
Macrolide
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Dihydropyranone
Phenol
Oxane
Benzenoid
Monosaccharide
Pyran
Monocyclic benzene moiety
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Polyol
Acetal
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Carboxylic acid
Organic oxide
Carbonyl group
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
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	3.32	ALOGPS
logP	2.85	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	2.72	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	447.09 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	210.91 m³·mol⁻¹	ChemAxon
Polarizability	83.39 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	No	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

8923761

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10748436

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Geraniinic acid C (NP0074256)

MOL for NP0074256 (Geraniinic acid C)

3D MOL for NP0074256 (Geraniinic acid C)

3D SDF for NP0074256 (Geraniinic acid C)

3D-SDF for NP0074256 (Geraniinic acid C)

PDB for NP0074256 (Geraniinic acid C)

3D PDB for NP0074256 (Geraniinic acid C)

SMILES for NP0074256 (Geraniinic acid C)

INCHI for NP0074256 (Geraniinic acid C)

Structure for NP0074256 (Geraniinic acid C)

3D Structure for NP0074256 (Geraniinic acid C)