NP-MRD: Showing NP-Card for (2r,3r,4s)-5,7-dihydroxy-4-(2,4,6-trihydroxyphenyl)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate (NP0254074)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 18:07:43 UTC

Updated at

2022-09-07 18:07:43 UTC

NP-MRD ID

NP0254074

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4s)-5,7-dihydroxy-4-(2,4,6-trihydroxyphenyl)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

Description

(2R,3R,4S)-5,7-dihydroxy-4-(2,4,6-trihydroxyphenyl)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin. (2r,3r,4s)-5,7-dihydroxy-4-(2,4,6-trihydroxyphenyl)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate is found in Morella rubra and Psidium guajava. Based on a literature review very few articles have been published on (2R,3R,4S)-5,7-dihydroxy-4-(2,4,6-trihydroxyphenyl)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072220072D          

 42 46  0  0  1  0            999 V2000
   -1.1994   -1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3428    0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  4 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 25 33  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 34 42  1  0  0  0  0
M  END

     RDKit          3D

 64 68  0  0  0  0  0  0  0  0999 V2000
    1.3218   -0.0050    1.9744 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6836    0.1192    0.7695 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6830    0.0466   -0.1784 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6768   -0.1543    0.1526 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2184   -1.4461   -0.4218 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8484   -2.2746    0.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1508   -2.1482    1.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9941   -1.2734    0.4040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7076   -2.8970    2.0775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8822   -3.7859    2.7143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3697   -4.5538    3.7626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5641   -3.9680    2.3680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0702   -3.2143    1.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2610   -3.3605    0.9424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8759   -1.3152   -1.7145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3833   -2.3893   -2.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3405   -3.7086   -1.9388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0137   -2.2064   -3.6243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1474   -0.9869   -4.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7807   -0.8435   -5.4591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6336    0.0918   -3.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0066   -0.0559   -2.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4944    1.0653   -1.6638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4284    1.0674   -0.2756 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7025    2.2587    0.2561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1766    2.9844    1.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5162    4.0848    1.8328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9816    4.8170    2.9108 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6565    4.4773    1.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3198    5.5816    1.7362 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1481    3.7782    0.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3273    4.2033   -0.4015 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4654    2.6748   -0.3135 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0841    0.3263    0.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0399    0.3917    1.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3770    0.5880    1.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3217    0.6501    2.1376 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7819    0.7225   -0.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1155    0.9203   -0.5145 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8401    0.6599   -1.1866 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2315    0.7932   -2.4953 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5015    0.4627   -0.8732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7393   -0.2344    1.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2492   -2.0279   -0.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8997   -0.6521   -0.3320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7470   -2.7667    2.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3073   -4.5032    4.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9256   -4.6913    2.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8253   -4.0221    1.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9122   -3.9665   -1.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4159   -3.0627   -4.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7694   -0.6800   -5.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7309    1.0650   -4.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4557    1.1501    0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1027    2.6502    1.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8636    4.5170    3.3540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9490    6.0913    2.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7894    3.7842   -1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8769    2.1532   -1.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7334    0.2877    2.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0590    0.5551    3.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4027    1.0177   -1.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5409    0.7473   -3.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7459    0.4104   -1.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  9  2  0
  9  7  1  0
  7  8  1  0
  7  6  2  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  1  0
 36 38  2  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 40 42  2  0
  4 24  1  0
 24 23  1  0
 23 22  1  0
 22 21  2  0
 21 19  1  0
 19 20  1  0
 19 18  2  0
 18 16  1  0
 16 17  1  0
 16 15  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  2  0
  6 13  1  0
 13 14  1  0
 13 12  2  0
 12 10  1  0
 15  5  1  0
 33 25  1  0
 42 34  1  0
 15 22  1  0
 11 47  1  0
  9 46  1  0
  8 45  1  0
  5 44  1  6
  4 43  1  1
 35 60  1  0
 37 61  1  0
 39 62  1  0
 41 63  1  0
 42 64  1  0
 24 54  1  1
 21 53  1  0
 20 52  1  0
 18 51  1  0
 17 50  1  0
 26 55  1  0
 28 56  1  0
 30 57  1  0
 32 58  1  0
 33 59  1  0
 14 49  1  0
 12 48  1  0
M  END


  Mrv1652309072220072D          

 42 46  0  0  1  0            999 V2000
   -1.1994   -1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3428    0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  4 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 25 33  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 34 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0254074

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C([C@@H]2[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC3=CC(O)=CC(O)=C23)C2=CC(O)=C(O)C(O)=C2)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H22O14/c29-11-5-13(31)21(14(32)6-11)23-22-15(33)7-12(30)8-20(22)41-26(9-1-16(34)24(38)17(35)2-9)27(23)42-28(40)10-3-18(36)25(39)19(37)4-10/h1-8,23,26-27,29-39H/t23-,26+,27+/m0/s1

> <INCHI_KEY>
CKLKGGJPKUDOSB-HUROMRQRSA-N

> <FORMULA>
C28H22O14

> <MOLECULAR_WEIGHT>
582.47

> <EXACT_MASS>
582.100955388

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
53.997661967034

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S)-5,7-dihydroxy-4-(2,4,6-trihydroxyphenyl)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

> <JCHEM_LOGP>
3.664226411333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.682855653337846

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.984137669114932

> <JCHEM_PKA_STRONGEST_BASIC>
-5.4337148508508575

> <JCHEM_POLAR_SURFACE_AREA>
258.05999999999995

> <JCHEM_REFRACTIVITY>
142.2546

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S)-5,7-dihydroxy-4-(2,4,6-trihydroxyphenyl)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0      -2.239  -2.016   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.240   1.246   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   24                                                  
CONECT    5    4    6   15                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    6   14                                                  
CONECT   14   13                                                            
CONECT   15    5   16   22                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   15   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23    4   25                                                  
CONECT   25   24   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   25                                                       
CONECT   34    2   35   42                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   34                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
(2R,3R,4S)-5,7-Dihydroxy-4-(2,4,6-trihydroxyphenyl)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₂₈H₂₂O₁₄

Average Mass

582.4700 Da

Monoisotopic Mass

582.10096 Da

IUPAC Name

(2R,3R,4S)-5,7-dihydroxy-4-(2,4,6-trihydroxyphenyl)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

Traditional Name

(2R,3R,4S)-5,7-dihydroxy-4-(2,4,6-trihydroxyphenyl)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

OC1=CC(O)=C([C@@H]2[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](OC3=CC(O)=CC(O)=C23)C2=CC(O)=C(O)C(O)=C2)C(O)=C1

InChI Identifier

InChI=1S/C28H22O14/c29-11-5-13(31)21(14(32)6-11)23-22-15(33)7-12(30)8-20(22)41-26(9-1-16(34)24(38)17(35)2-9)27(23)42-28(40)10-3-18(36)25(39)19(37)4-10/h1-8,23,26-27,29-39H/t23-,26+,27+/m0/s1

InChI Key

CKLKGGJPKUDOSB-HUROMRQRSA-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
Morella rubra	LOTUS Database	35616633
Psidium guajava	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Catechin gallates

Alternative Parents

Substituents

Catechin gallate
Epigallocatechin
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Neoflavan
Neoflavonoid skeleton
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzopyran
Chromane
1-benzopyran
Benzoate ester
Pyrogallol derivative
Benzenetriol
Phloroglucinol derivative
Benzoic acid or derivatives
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid ester
Ether
Monocarboxylic acid or derivatives
Polyol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Organic oxide
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	3.66	ChemAxon
pKa (Strongest Acidic)	7.98	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	258.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	142.25 m³·mol⁻¹	ChemAxon
Polarizability	54 Å³	ChemAxon
Number of Rings	5	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

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

163093723

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r,4s)-5,7-dihydroxy-4-(2,4,6-trihydroxyphenyl)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate (NP0254074)

MOL for NP0254074 ((2r,3r,4s)-5,7-dihydroxy-4-(2,4,6-trihydroxyphenyl)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate)

3D MOL for NP0254074 ((2r,3r,4s)-5,7-dihydroxy-4-(2,4,6-trihydroxyphenyl)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate)

3D SDF for NP0254074 ((2r,3r,4s)-5,7-dihydroxy-4-(2,4,6-trihydroxyphenyl)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate)

3D-SDF for NP0254074 ((2r,3r,4s)-5,7-dihydroxy-4-(2,4,6-trihydroxyphenyl)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate)

PDB for NP0254074 ((2r,3r,4s)-5,7-dihydroxy-4-(2,4,6-trihydroxyphenyl)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate)

3D PDB for NP0254074 ((2r,3r,4s)-5,7-dihydroxy-4-(2,4,6-trihydroxyphenyl)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate)

SMILES for NP0254074 ((2r,3r,4s)-5,7-dihydroxy-4-(2,4,6-trihydroxyphenyl)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate)

INCHI for NP0254074 ((2r,3r,4s)-5,7-dihydroxy-4-(2,4,6-trihydroxyphenyl)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate)

Structure for NP0254074 ((2r,3r,4s)-5,7-dihydroxy-4-(2,4,6-trihydroxyphenyl)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate)

3D Structure for NP0254074 ((2r,3r,4s)-5,7-dihydroxy-4-(2,4,6-trihydroxyphenyl)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate)