NP-MRD: Showing NP-Card for [(2r,3r,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate (NP0297073)

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Record Information

Version

2.0

Created at

2022-09-10 07:04:44 UTC

Updated at

2022-09-10 07:04:44 UTC

NP-MRD ID

NP0297073

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3r,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate

Description

[(2R,3R,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2E)-3-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. [(2r,3r,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate is found in Verbascum thapsus. Based on a literature review very few articles have been published on [(2R,3R,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2E)-3-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102209042D          

 55 59  0  0  1  0            999 V2000
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 C   0  0  2  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
   -0.7145   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -12.7875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -12.7875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -13.6125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579  -14.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -14.0250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868  -14.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -13.6125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7158  -14.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  1  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
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 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  2  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  1  0  0  0
 19 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 16 34  1  0  0  0  0
  9 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  2  0  0  0  0
 40 47  1  0  0  0  0
 36 48  1  0  0  0  0
  6 48  1  0  0  0  0
 48 49  1  6  0  0  0
  4 50  1  0  0  0  0
 50 51  1  1  0  0  0
 50 52  1  0  0  0  0
 52 53  1  1  0  0  0
 52 54  1  0  0  0  0
  2 54  1  0  0  0  0
 54 55  1  6  0  0  0
M  END

     RDKit          3D

101105  0  0  0  0  0  0  0  0999 V2000
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   -8.0227   -2.0189    1.9280 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.5492   -3.2140   -1.3059 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3202   -4.1953   -0.3457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3006   -2.3216   -1.3247 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1226   -3.2205   -1.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1212   -2.6348   -1.3444 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6845   -1.6664   -2.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0426   -1.2232   -3.1050 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7739   -1.5378   -0.8943 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0952   -1.0640   -0.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7704   -0.1223   -1.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0366    0.3252   -0.9686 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7004   -0.1611    0.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9590    0.2269    0.5399 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7220    1.1680   -0.1327 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0167    0.7180   -0.4113 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.8878    1.2229   -1.8350 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3938   -1.3209   -2.2493 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1896    3.3186    1.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9565    4.4925    1.8449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4890    5.6876    1.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2454    6.8516    2.1626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2791    5.7515    0.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8132    6.9636   -0.0927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4954    4.5906   -0.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7127   -1.2058   -1.9616 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8121   -0.3823   -1.8842 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1876   -5.1771    0.2639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8291   -4.4898    1.7849 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.6797   -5.0179    0.8103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4665   -3.3329    2.4665 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.2935   -3.3545    3.8505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0914   -0.2172    1.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0448   -1.4532    2.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9117   -0.4493    3.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1213   -1.6975    2.5237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6393   -2.2581    1.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3859   -1.8195    0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6637   -3.6183   -2.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6517   -3.9397    0.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3116   -1.8323   -0.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1285   -3.7825   -2.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1944   -3.9931   -0.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4352   -0.3644   -2.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3316   -2.3055   -0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2953    0.3034   -2.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4652    1.0729   -1.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2739    1.4063   -1.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9673    2.1415   -1.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5413    0.5203   -2.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5769    0.7623   -1.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2533    2.0822   -3.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0998    2.7518    0.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1673    4.1355   -1.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2559   -2.3146    1.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2227   -0.3147   -0.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.2354    2.2118   -1.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2216    1.2963   -0.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7403    2.3902    1.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6785    6.8158    2.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
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 54100  1  1
 55101  1  0
M  END


  Mrv1652309102209042D          

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    0.7145   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
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  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
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 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
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 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  1  0  0  0
 19 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 16 34  1  0  0  0  0
  9 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  2  0  0  0  0
 40 47  1  0  0  0  0
 36 48  1  0  0  0  0
  6 48  1  0  0  0  0
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  4 50  1  0  0  0  0
 50 51  1  1  0  0  0
 50 52  1  0  0  0  0
 52 53  1  1  0  0  0
 52 54  1  0  0  0  0
  2 54  1  0  0  0  0
 54 55  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0297073

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](COC(=O)\C=C\C3=CC=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(O)=C3)O[C@@H](OCCC3=CC=C(O)C(O)=C3)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C35H46O20/c1-14-24(41)27(44)29(46)34(51-14)55-32-26(43)22(54-33(31(32)48)49-9-8-16-2-5-17(37)18(38)10-16)13-50-23(40)7-4-15-3-6-20(19(39)11-15)52-35-30(47)28(45)25(42)21(12-36)53-35/h2-7,10-11,14,21-22,24-39,41-48H,8-9,12-13H2,1H3/b7-4+/t14-,21+,22+,24-,25+,26+,27+,28-,29+,30+,31+,32-,33+,34+,35+/m0/s1

> <INCHI_KEY>
NZPAYFATRXWJOI-QIMSETSCSA-N

> <FORMULA>
C35H46O20

> <MOLECULAR_WEIGHT>
786.733

> <EXACT_MASS>
786.258243881

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
101

> <JCHEM_AVERAGE_POLARIZABILITY>
77.52096724098114

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3R,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2E)-3-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate

> <JCHEM_LOGP>
-1.4486427329999982

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.869210740365267

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.241906886959239

> <JCHEM_PKA_STRONGEST_BASIC>
-3.676505494673579

> <JCHEM_POLAR_SURFACE_AREA>
324.44

> <JCHEM_REFRACTIVITY>
180.5475

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2E)-3-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.667 -12.320   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.335 -13.860   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -8.002 -13.860   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0     -10.669 -13.860   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -9.336 -16.170   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -10.669 -16.940   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -10.669 -18.480   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -12.003 -19.250   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -12.003 -20.790   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -10.669 -21.560   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0     -10.669 -23.100   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -9.336 -23.870   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -8.002 -23.100   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -6.668 -23.870   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.335 -23.100   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.001 -23.870   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -6.668 -25.410   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -5.335 -26.180   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -8.002 -26.180   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -8.002 -27.720   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -9.336 -25.410   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0     -10.669 -26.180   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -9.336 -20.790   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -8.002 -21.560   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -9.336 -19.250   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0     -12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -0.000 -13.860   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   54                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   50                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   48                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   35                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   34                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   32                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   21   31                                                  
CONECT   31   30                                                            
CONECT   32   19   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   16                                                       
CONECT   35    9   36                                                       
CONECT   36   35   37   48                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41   47                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   40                                                       
CONECT   48   36    6   49                                                  
CONECT   49   48                                                            
CONECT   50    4   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52    2   55                                                  
CONECT   55   54                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  118    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3R,4S,5R,6R)-6-[2-(3,4-Dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-{[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2E)-3-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid	Generator

Chemical Formula

C₃₅H₄₆O₂₀

Average Mass

786.7330 Da

Monoisotopic Mass

786.25824 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](COC(=O)\C=C\C3=CC=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(O)=C3)O[C@@H](OCCC3=CC=C(O)C(O)=C3)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C35H46O20/c1-14-24(41)27(44)29(46)34(51-14)55-32-26(43)22(54-33(31(32)48)49-9-8-16-2-5-17(37)18(38)10-16)13-50-23(40)7-4-15-3-6-20(19(39)11-15)52-35-30(47)28(45)25(42)21(12-36)53-35/h2-7,10-11,14,21-22,24-39,41-48H,8-9,12-13H2,1H3/b7-4+/t14-,21+,22+,24-,25+,26+,27+,28-,29+,30+,31+,32-,33+,34+,35+/m0/s1

InChI Key

NZPAYFATRXWJOI-QIMSETSCSA-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
Verbascum thapsus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Coumaric acid or derivatives
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Cinnamic acid or derivatives
Disaccharide
O-glycosyl compound
Tyrosol derivative
Phenol ether
Phenoxy compound
Styrene
Catechol
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Fatty acid ester
Monocyclic benzene moiety
Oxane
Benzenoid
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Primary alcohol
Carbonyl group
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	-1.4	ChemAxon
pKa (Strongest Acidic)	9.24	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	324.44 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	180.55 m³·mol⁻¹	ChemAxon
Polarizability	77.52 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	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

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

163189009

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,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate (NP0297073)

MOL for NP0297073 ([(2r,3r,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate)

3D MOL for NP0297073 ([(2r,3r,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate)

3D SDF for NP0297073 ([(2r,3r,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate)

3D-SDF for NP0297073 ([(2r,3r,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate)

PDB for NP0297073 ([(2r,3r,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate)

3D PDB for NP0297073 ([(2r,3r,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate)

SMILES for NP0297073 ([(2r,3r,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate)

INCHI for NP0297073 ([(2r,3r,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate)

Structure for NP0297073 ([(2r,3r,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate)

3D Structure for NP0297073 ([(2r,3r,4s,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]methyl (2e)-3-(3-hydroxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate)