NP-MRD: Showing NP-Card for (2s,3r,4s,5r)-2-{[(3s)-1,7-bis(3,4-dihydroxyphenyl)-5-oxoheptan-3-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0229919)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-06 10:11:25 UTC

Updated at

2022-09-06 10:11:26 UTC

NP-MRD ID

NP0229919

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5r)-2-{[(3s)-1,7-bis(3,4-dihydroxyphenyl)-5-oxoheptan-3-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate

Description

Oregonoyl A belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain. (2s,3r,4s,5r)-2-{[(3s)-1,7-bis(3,4-dihydroxyphenyl)-5-oxoheptan-3-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate is found in Alnus japonica. Based on a literature review very few articles have been published on oregonoyl A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062212112D          

 45 48  0  0  1  0            999 V2000
    8.7947   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3822   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3197   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9072   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822   -3.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697   -2.6961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9072   -3.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7947   -5.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6197   -5.5539    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0322   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6197   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0322   -3.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6197   -2.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0322   -1.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572   -1.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2697   -1.2671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2697   -2.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -2.6961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572   -3.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0322   -6.2684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572   -6.2684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.2697   -5.5539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -5.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5072   -6.2684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.3322   -6.2684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -6.9829    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.5072   -7.6974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2697   -6.9829    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8572   -7.6974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2697   -8.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -8.4118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572   -9.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2697   -9.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572  -10.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2697  -11.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572  -11.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0322  -11.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6197  -12.6987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6197  -11.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0322  -10.5552    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 17 24  1  0  0  0  0
 14 25  1  6  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 26 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  2  0  0  0  0
 39 45  1  0  0  0  0
M  END

     RDKit          3D

 81 84  0  0  0  0  0  0  0  0999 V2000
   -2.8322   -1.5572    2.1653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3265   -1.0310    1.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7982   -1.5237   -0.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6710   -2.7130   -0.1762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9476   -2.6639    0.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0571   -3.2316    1.7772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2550   -3.1912    2.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3667   -2.5754    1.9655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5583   -2.5292    2.6708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2759   -2.0016    0.7129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3609   -1.3643    0.1163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0835   -2.0581    0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3358   -0.0056    1.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7642    0.8097    0.3391 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4527    2.0291   -0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5757    2.0207   -1.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9829    3.4433   -1.2281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4277    4.2355   -2.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8253    5.5603   -2.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8084    6.0614   -1.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2260    7.3705   -1.6655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3802    5.2888   -0.5498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3611    5.8248    0.2715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9543    3.9710   -0.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1505    0.0241   -0.6067 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2146    0.0357   -0.6259 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6027    0.6610   -1.7974 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8868   -0.1898   -2.8415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1872   -1.5336   -2.6953 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5506   -2.3686   -3.7787 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5684   -2.2546   -1.4458 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4689   -2.9833   -0.9846 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9344   -1.2336   -0.4064 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3419   -0.9311   -0.4771 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2259   -1.1485    0.5451 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7898   -1.6489    1.6403 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6278   -0.8188    0.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4619   -1.0316    1.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9001   -0.7431    1.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6432   -1.0180    2.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0000   -0.7724    2.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6102   -0.2430    1.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9666   -0.0049    1.3667 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8759    0.0386    0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4974   -0.2130    0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3378   -0.7294   -0.7245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8810   -1.6998   -0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9285   -2.8806   -1.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1748   -3.6631    0.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2541   -3.7576    2.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3202   -3.6389    3.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6261   -2.9401    3.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2212   -1.3334    0.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0379   -1.5997   -0.9494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4662   -0.4267    2.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7734    0.7250    2.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1874    1.2659    0.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8301    2.5366    0.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6862    2.7516   -0.4833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5050    1.5328   -0.6528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3715    1.6020   -2.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6582    3.8765   -2.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3826    6.1890   -3.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8172    7.9441   -2.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7993    5.2566    1.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4403    3.3956    0.3745 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6023    0.7360    0.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9683   -0.3099   -3.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4474    0.2689   -3.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0895   -1.4197   -2.7354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4014   -2.8188   -3.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4060   -2.9830   -1.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053   -3.9582   -1.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8090   -1.6558    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9697   -0.4029   -0.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0307   -1.4620    2.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1331   -1.4358    3.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5415   -1.0061    3.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5244   -0.2050    2.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3110    0.4509   -0.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9079    0.0032   -0.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 29  1  0
 29 28  1  0
 28 27  1  0
 27 26  1  0
 26 25  1  0
 25 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  2  0
 14 13  1  0
 13  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 26 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  2  0
 35 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 42 44  1  0
 44 45  2  0
 33 31  1  0
 31 32  1  0
 31 29  1  0
 24 17  1  0
 12  5  1  0
 45 39  1  0
 30 71  1  0
 29 70  1  1
 28 68  1  0
 28 69  1  0
 26 67  1  1
 14 57  1  1
 15 58  1  0
 15 59  1  0
 16 60  1  0
 16 61  1  0
 18 62  1  0
 19 63  1  0
 21 64  1  0
 23 65  1  0
 24 66  1  0
 13 55  1  0
 13 56  1  0
  3 46  1  0
  3 47  1  0
  4 48  1  0
  4 49  1  0
  6 50  1  0
  7 51  1  0
  9 52  1  0
 11 53  1  0
 12 54  1  0
 33 74  1  1
 37 75  1  0
 38 76  1  0
 40 77  1  0
 41 78  1  0
 43 79  1  0
 44 80  1  0
 45 81  1  0
 31 72  1  6
 32 73  1  0
M  END


  Mrv1652309062212112D          

 45 48  0  0  1  0            999 V2000
    8.7947   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3822   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3197   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9072   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822   -3.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697   -2.6961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9072   -3.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7947   -5.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6197   -5.5539    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0322   -4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6197   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0322   -3.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6197   -2.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0322   -1.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572   -1.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2697   -1.2671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2697   -2.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -2.6961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572   -3.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0322   -6.2684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572   -6.2684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.2697   -5.5539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -5.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5072   -6.2684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.3322   -6.2684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -6.9829    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.5072   -7.6974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2697   -6.9829    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8572   -7.6974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2697   -8.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0947   -8.4118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572   -9.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2697   -9.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572  -10.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2697  -11.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572  -11.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0322  -11.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6197  -12.6987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6197  -11.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0322  -10.5552    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 17 24  1  0  0  0  0
 14 25  1  6  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 26 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  2  0  0  0  0
 39 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0229919

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1CO[C@@H](O[C@@H](CCC2=CC=C(O)C(O)=C2)CC(=O)CCC2=CC=C(O)C(O)=C2)[C@H](OC(=O)\C=C\C2=CC=C(O)C=C2)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C33H36O12/c34-22-8-1-19(2-9-22)7-14-30(41)45-32-31(42)29(40)18-43-33(32)44-24(11-4-21-6-13-26(37)28(39)16-21)17-23(35)10-3-20-5-12-25(36)27(38)15-20/h1-2,5-9,12-16,24,29,31-34,36-40,42H,3-4,10-11,17-18H2/b14-7+/t24-,29+,31-,32+,33-/m0/s1

> <INCHI_KEY>
QIBTYQFSZFGWCS-YETGDIJESA-N

> <FORMULA>
C33H36O12

> <MOLECULAR_WEIGHT>
624.639

> <EXACT_MASS>
624.220676599

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
63.96507181848581

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R)-2-{[(3S)-1,7-bis(3,4-dihydroxyphenyl)-5-oxoheptan-3-yl]oxy}-4,5-dihydroxyoxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
4.6979864466666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.398466714653836

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.912274325164123

> <JCHEM_PKA_STRONGEST_BASIC>
-3.527310390817888

> <JCHEM_POLAR_SURFACE_AREA>
203.43999999999997

> <JCHEM_REFRACTIVITY>
161.48109999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R)-2-{[(3S)-1,7-bis(3,4-dihydroxyphenyl)-5-oxoheptan-3-yl]oxy}-4,5-dihydroxyoxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0      16.417  -7.700   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      15.647  -9.034   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.107  -9.034   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.797  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.027  -9.034   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.487  -9.034   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.717  -7.700   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.177  -7.700   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.487  -6.366   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.717  -5.033   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      11.027  -6.366   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.417 -10.367   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.957 -10.367   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.727  -9.034   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.957  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.727  -6.366   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.957  -5.033   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.727  -3.699   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      20.267  -3.699   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      21.037  -2.365   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      21.037  -5.033   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      22.577  -5.033   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      20.267  -6.366   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      18.727 -11.701   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      20.267 -11.701   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      21.037 -10.367   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      22.577 -10.367   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      23.347 -11.701   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      24.887 -11.701   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      22.577 -13.035   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      23.347 -14.368   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      21.037 -13.035   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      20.267 -14.368   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      21.037 -15.702   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      22.577 -15.702   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      20.267 -17.036   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      21.037 -18.369   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      20.267 -19.703   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      21.037 -21.037   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      20.267 -22.370   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      18.727 -22.370   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      17.957 -23.704   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      17.957 -21.037   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      18.727 -19.703   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5                                                       
CONECT   13    2   14                                                       
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   17                                                       
CONECT   25   14   26                                                       
CONECT   26   25   27   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   26   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   45                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44   39                                                       
MASTER        0    0    0    0    0    0    0    0   45    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₃₆O₁₂

Average Mass

624.6390 Da

Monoisotopic Mass

624.22068 Da

IUPAC Name

(2S,3R,4S,5R)-2-{[(3S)-1,7-bis(3,4-dihydroxyphenyl)-5-oxoheptan-3-yl]oxy}-4,5-dihydroxyoxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

(2S,3R,4S,5R)-2-{[(3S)-1,7-bis(3,4-dihydroxyphenyl)-5-oxoheptan-3-yl]oxy}-4,5-dihydroxyoxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

O[C@@H]1CO[C@@H](O[C@@H](CCC2=CC=C(O)C(O)=C2)CC(=O)CCC2=CC=C(O)C(O)=C2)[C@H](OC(=O)\C=C\C2=CC=C(O)C=C2)[C@H]1O

InChI Identifier

InChI=1S/C33H36O12/c34-22-8-1-19(2-9-22)7-14-30(41)45-32-31(42)29(40)18-43-33(32)44-24(11-4-21-6-13-26(37)28(39)16-21)17-23(35)10-3-20-5-12-25(36)27(38)15-20/h1-2,5-9,12-16,24,29,31-34,36-40,42H,3-4,10-11,17-18H2/b14-7+/t24-,29+,31-,32+,33-/m0/s1

InChI Key

QIBTYQFSZFGWCS-YETGDIJESA-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
Alnus japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Linear diarylheptanoids

Alternative Parents

Substituents

Linear 1,7-diphenylheptane skeleton
Coumaric acid ester
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Monosaccharide
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Ketone
Secondary alcohol
1,2-diol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Acetal
Oxacycle
Carboxylic acid derivative
Alcohol
Organic oxygen compound
Carbonyl group
Organic oxide
Aldehyde
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.7	ChemAxon
pKa (Strongest Acidic)	8.91	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.44 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	161.48 m³·mol⁻¹	ChemAxon
Polarizability	63.97 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

24644548

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44602673

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5r)-2-{[(3s)-1,7-bis(3,4-dihydroxyphenyl)-5-oxoheptan-3-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate (NP0229919)

MOL for NP0229919 ((2s,3r,4s,5r)-2-{[(3s)-1,7-bis(3,4-dihydroxyphenyl)-5-oxoheptan-3-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D MOL for NP0229919 ((2s,3r,4s,5r)-2-{[(3s)-1,7-bis(3,4-dihydroxyphenyl)-5-oxoheptan-3-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D SDF for NP0229919 ((2s,3r,4s,5r)-2-{[(3s)-1,7-bis(3,4-dihydroxyphenyl)-5-oxoheptan-3-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D-SDF for NP0229919 ((2s,3r,4s,5r)-2-{[(3s)-1,7-bis(3,4-dihydroxyphenyl)-5-oxoheptan-3-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

PDB for NP0229919 ((2s,3r,4s,5r)-2-{[(3s)-1,7-bis(3,4-dihydroxyphenyl)-5-oxoheptan-3-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D PDB for NP0229919 ((2s,3r,4s,5r)-2-{[(3s)-1,7-bis(3,4-dihydroxyphenyl)-5-oxoheptan-3-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

SMILES for NP0229919 ((2s,3r,4s,5r)-2-{[(3s)-1,7-bis(3,4-dihydroxyphenyl)-5-oxoheptan-3-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

INCHI for NP0229919 ((2s,3r,4s,5r)-2-{[(3s)-1,7-bis(3,4-dihydroxyphenyl)-5-oxoheptan-3-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

Structure for NP0229919 ((2s,3r,4s,5r)-2-{[(3s)-1,7-bis(3,4-dihydroxyphenyl)-5-oxoheptan-3-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)

3D Structure for NP0229919 ((2s,3r,4s,5r)-2-{[(3s)-1,7-bis(3,4-dihydroxyphenyl)-5-oxoheptan-3-yl]oxy}-4,5-dihydroxyoxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate)