NP-MRD: Showing NP-Card for 1-(2e)-3-(3-hydroxy-5-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-yl 5-methyl 3-hydroxy-3-methylpentanedioate (NP0190976)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 07:45:46 UTC

Updated at

2022-09-04 07:45:46 UTC

NP-MRD ID

NP0190976

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(2e)-3-(3-hydroxy-5-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-yl 5-methyl 3-hydroxy-3-methylpentanedioate

Description

1-(2E)-3-(3-hydroxy-5-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-yl 5-methyl 3-hydroxy-3-methylpentanedioate belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety. 1-(2e)-3-(3-hydroxy-5-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-yl 5-methyl 3-hydroxy-3-methylpentanedioate is found in Wahlenbergia marginata. Based on a literature review very few articles have been published on 1-(2E)-3-(3-hydroxy-5-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-yl 5-methyl 3-hydroxy-3-methylpentanedioate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042209452D          

 36 37  0  0  1  0            999 V2000
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    3.3000    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   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
   -0.7145   -1.2375    0.0000 C   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
   -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
   -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
    0.0000   -4.1250    0.0000 C   0  0  2  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   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    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   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   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 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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  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 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  1  0  0  0
 20 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 36  2  0  0  0  0
 16 36  1  0  0  0  0
M  END

     RDKit          3D

 68 69  0  0  0  0  0  0  0  0999 V2000
    7.6540    0.5074    2.8046 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7183    1.0991    1.5173 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3397    0.3382    0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9649   -0.8262    0.5772 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4000    0.9337   -0.9485 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7524    0.1535   -2.0497 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0559    0.9840   -3.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2898   -1.0928   -2.2753 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2592    0.1700   -1.9943 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6273   -0.3604   -0.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3134    0.4172    0.1289 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3565   -1.7049   -0.6999 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7339   -2.2637    0.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3445   -1.8221    0.6218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7072   -0.9804   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3357   -0.5771    0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2541    0.3528   -0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5582    0.7948   -0.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0164    1.7260   -1.3969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3123    0.3313    0.5736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5844    0.7882    0.7576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7859    0.2749    0.2906 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3498    1.2044   -0.5836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5117    0.8281   -1.1822 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2066    2.1328   -1.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4143    1.8845   -2.2369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5050    0.0871   -0.3693 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.1806   -0.8108   -1.2200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9336   -0.7305    0.7487 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.9588   -0.9995    1.6598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8238    0.0965    1.3802 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3520   -0.4545    2.5393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7210   -0.5989    1.4118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3753   -1.1378    2.4991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7917   -2.0819    3.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4099   -1.0371    1.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5927    0.5172    3.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3123    1.0745    3.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9936   -0.5430    2.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4909    1.0565   -1.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9353    1.9516   -0.9569 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0124    0.6494   -3.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1637    2.0438   -3.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2676    0.8618   -4.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5399   -1.7369   -2.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9174   -0.4486   -2.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9455    1.2217   -2.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7794   -3.3873    0.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3263   -2.0229    1.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8730   -2.2745    1.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1967   -0.5835   -1.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3192    0.7335   -1.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9330    2.1228   -1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6615   -0.6873   -0.2881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3179    0.2949   -2.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4359    2.6508   -0.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5196    2.7628   -2.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3982    1.2120   -2.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2956    0.7577    0.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9028   -1.2967   -0.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4644   -1.6903    0.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6346   -1.6252    2.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2948    1.1098    1.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8949    0.2836    3.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4301   -2.9408    2.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8632   -1.6514    3.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4527   -2.4108    4.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0262   -1.7687    1.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  6
  6  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 20 33  1  0
 33 34  1  0
 34 35  1  0
 33 36  2  0
 36 16  1  0
 31 22  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  5 40  1  0
  5 41  1  0
  7 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 15 51  1  0
 17 52  1  0
 19 53  1  0
 22 54  1  6
 24 55  1  6
 25 56  1  0
 25 57  1  0
 26 58  1  0
 27 59  1  1
 28 60  1  0
 29 61  1  6
 30 62  1  0
 31 63  1  1
 32 64  1  0
 35 65  1  0
 35 66  1  0
 35 67  1  0
 36 68  1  0
M  END


  Mrv1652309042209452D          

 36 37  0  0  1  0            999 V2000
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    3.3000    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   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
   -0.7145   -1.2375    0.0000 C   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
   -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
   -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
    0.0000   -4.1250    0.0000 C   0  0  2  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   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    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   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   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 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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  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 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  1  0  0  0
 20 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 36  2  0  0  0  0
 16 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0190976

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC(C)(O)CC(=O)OC\C=C\C1=CC(O)=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O13/c1-23(31,9-16(26)33-3)10-17(27)34-6-4-5-12-7-13(25)21(14(8-12)32-2)36-22-20(30)19(29)18(28)15(11-24)35-22/h4-5,7-8,15,18-20,22,24-25,28-31H,6,9-11H2,1-3H3/b5-4+/t15-,18-,19+,20-,22+,23?/m1/s1

> <INCHI_KEY>
NLGNIMSESLPIFG-RBUWDIGISA-N

> <FORMULA>
C23H32O13

> <MOLECULAR_WEIGHT>
516.496

> <EXACT_MASS>
516.18429109

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
51.635026667399785

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(2E)-3-(3-hydroxy-5-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-yl 5-methyl 3-hydroxy-3-methylpentanedioate

> <JCHEM_LOGP>
-1.1549343406666672

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.19934349444203

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.738066507422243

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092366204317

> <JCHEM_POLAR_SURFACE_AREA>
201.66999999999996

> <JCHEM_REFRACTIVITY>
121.17650000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
1-(2E)-3-(3-hydroxy-5-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-yl 5-methyl 3-hydroxy-3-methylpentanedioate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  10.010   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.335   7.700   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.207   6.160   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.127   6.160   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.000   4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   36                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   33                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   22   32                                                  
CONECT   32   31                                                            
CONECT   33   20   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   16                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Value	Source
1-(2E)-3-(3-Hydroxy-5-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-yl 5-methyl 3-hydroxy-3-methylpentanedioic acid	Generator

Chemical Formula

C₂₃H₃₂O₁₃

Average Mass

516.4960 Da

Monoisotopic Mass

516.18429 Da

IUPAC Name

1-(2E)-3-(3-hydroxy-5-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-yl 5-methyl 3-hydroxy-3-methylpentanedioate

Traditional Name

1-(2E)-3-(3-hydroxy-5-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-yl 5-methyl 3-hydroxy-3-methylpentanedioate

CAS Registry Number

Not Available

SMILES

COC(=O)CC(C)(O)CC(=O)OC\C=C\C1=CC(O)=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(OC)=C1

InChI Identifier

InChI=1S/C23H32O13/c1-23(31,9-16(26)33-3)10-17(27)34-6-4-5-12-7-13(25)21(14(8-12)32-2)36-22-20(30)19(29)18(28)15(11-24)35-22/h4-5,7-8,15,18-20,22,24-25,28-31H,6,9-11H2,1-3H3/b5-4+/t15-,18-,19+,20-,22+,23?/m1/s1

InChI Key

NLGNIMSESLPIFG-RBUWDIGISA-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
Wahlenbergia marginata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Saccharolipids

Sub Class

Not Available

Direct Parent

Saccharolipids

Alternative Parents

Substituents

Saccharolipid
Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Methoxyphenol
Styrene
Phenol ether
Phenoxy compound
Methoxybenzene
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Fatty acid methyl ester
Phenol
Fatty acid ester
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Monosaccharide
Benzenoid
Oxane
Tertiary alcohol
Methyl ester
Secondary alcohol
Carboxylic acid ester
Polyol
Organoheterocyclic compound
Oxacycle
Acetal
Ether
Carboxylic acid derivative
Organooxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Primary alcohol
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	-1.2	ChemAxon
pKa (Strongest Acidic)	9.74	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	201.67 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	121.18 m³·mol⁻¹	ChemAxon
Polarizability	51.64 Å³	ChemAxon
Number of Rings	2	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

101701147

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(2e)-3-(3-hydroxy-5-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-yl 5-methyl 3-hydroxy-3-methylpentanedioate (NP0190976)

MOL for NP0190976 (1-(2e)-3-(3-hydroxy-5-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-yl 5-methyl 3-hydroxy-3-methylpentanedioate)

3D MOL for NP0190976 (1-(2e)-3-(3-hydroxy-5-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-yl 5-methyl 3-hydroxy-3-methylpentanedioate)

3D SDF for NP0190976 (1-(2e)-3-(3-hydroxy-5-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-yl 5-methyl 3-hydroxy-3-methylpentanedioate)

3D-SDF for NP0190976 (1-(2e)-3-(3-hydroxy-5-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-yl 5-methyl 3-hydroxy-3-methylpentanedioate)

PDB for NP0190976 (1-(2e)-3-(3-hydroxy-5-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-yl 5-methyl 3-hydroxy-3-methylpentanedioate)

3D PDB for NP0190976 (1-(2e)-3-(3-hydroxy-5-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-yl 5-methyl 3-hydroxy-3-methylpentanedioate)

SMILES for NP0190976 (1-(2e)-3-(3-hydroxy-5-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-yl 5-methyl 3-hydroxy-3-methylpentanedioate)

INCHI for NP0190976 (1-(2e)-3-(3-hydroxy-5-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-yl 5-methyl 3-hydroxy-3-methylpentanedioate)

Structure for NP0190976 (1-(2e)-3-(3-hydroxy-5-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-yl 5-methyl 3-hydroxy-3-methylpentanedioate)

3D Structure for NP0190976 (1-(2e)-3-(3-hydroxy-5-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-en-1-yl 5-methyl 3-hydroxy-3-methylpentanedioate)