NP-MRD: Showing NP-Card for (2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-{[(2s,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxybenzoate (NP0223375)

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Record Information

Version

2.0

Created at

2022-09-06 01:27:01 UTC

Updated at

2022-09-06 01:27:01 UTC

NP-MRD ID

NP0223375

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-{[(2s,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxybenzoate

Description

2-(2-O-Acetyl-beta-D-glucopyranosyloxy)-6-hydroxybenzoic acid 2-(beta-D-glucopyranosyloxy)benzyl ester 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. (2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-{[(2s,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxybenzoate is found in Viburnum cylindricum. Based on a literature review very few articles have been published on 2-(2-O-Acetyl-beta-D-glucopyranosyloxy)-6-hydroxybenzoic acid 2-(beta-D-glucopyranosyloxy)benzyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062203272D          

 44 47  0  0  1  0            999 V2000
    3.5724   -2.8875    0.0000 C   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
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    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
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    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
    7.1447   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4315   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.8605   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.8605   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4315   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    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
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
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  8 14  1  0  0  0  0
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 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
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 26 35  1  0  0  0  0
 35 36  1  1  0  0  0
  6 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  6  0  0  0
 39 40  1  0  0  0  0
 38 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
  5 43  1  0  0  0  0
 43 44  1  6  0  0  0
M  END

     RDKit          3D

 78 81  0  0  0  0  0  0  0  0999 V2000
   -6.9948    0.7806   -3.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6107    0.8519   -2.6844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7547    1.6342   -3.2138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1870    0.0897   -1.6056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8849    0.1597   -1.1054 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8537    0.6113    0.3458 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7451    1.4315    0.5526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8462    2.7281    0.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0030    3.4119    1.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0044    4.7469    1.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7896    5.4000    1.8125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6045    4.7465    1.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4061    2.7435    0.8741 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1790    0.0849   -2.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1246    1.4181   -1.8758 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6156   -2.2101   -1.6795 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6572   -2.7351   -0.8753 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4321   -3.0830   -1.4957 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2769   -3.9771   -2.5694 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1135   -2.3742   -1.3208 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1733   -3.2088   -0.7573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6936   -0.4852    1.2015 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3030   -2.1314   -0.4405 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.1014   -1.2445   -0.4286 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.0028    0.0977   -4.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3217    1.8027   -3.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8281    1.1045    0.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3993    6.3527    2.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3510    1.2550   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0071   -0.1825    4.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6643   -0.8751    2.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9472   -0.5338   -0.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6294    0.1038   -3.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2480   -0.1847   -2.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9982   -2.3356   -2.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2399   -2.0370   -0.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5427   -3.7566   -0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6699   -4.6834   -2.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8774   -3.8796   -1.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3720   -2.9651    1.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5589   -2.1489    2.9893 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0885   -1.5734   -2.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8224   -2.1571   -0.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
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 43 44  1  0
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 41 42  1  0
 41 38  1  0
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 39 40  1  0
 38 37  1  0
 37  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
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 31 32  1  0
 31 33  1  0
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 33 35  1  0
 35 36  1  0
  6  5  1  0
 14  8  1  0
 24 19  1  0
 35 26  1  0
  1 45  1  0
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  1 47  1  0
  5 48  1  6
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 41 75  1  1
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 40 74  1  0
  6 49  1  1
  9 50  1  0
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 11 52  1  0
 13 53  1  0
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 30 64  1  0
 31 65  1  6
 32 66  1  0
 33 67  1  1
 34 68  1  0
 35 69  1  6
 36 70  1  0
M  END


  Mrv1652309062203272D          

 44 47  0  0  1  0            999 V2000
    3.5724   -2.8875    0.0000 C   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
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    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    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
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    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    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
    7.1447   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2881   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4315   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.8605   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.8605   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4315   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    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
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  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
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  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  6  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 26 35  1  0  0  0  0
 35 36  1  1  0  0  0
  6 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  6  0  0  0
 39 40  1  0  0  0  0
 38 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
  5 43  1  0  0  0  0
 43 44  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0223375

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC(O)=C1C(=O)OCC1=CC=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H34O16/c1-12(31)40-25-23(36)21(34)18(10-30)44-28(25)42-16-8-4-6-14(32)19(16)26(38)39-11-13-5-2-3-7-15(13)41-27-24(37)22(35)20(33)17(9-29)43-27/h2-8,17-18,20-25,27-30,32-37H,9-11H2,1H3/t17-,18-,20-,21-,22+,23+,24-,25-,27-,28-/m1/s1

> <INCHI_KEY>
KGTNCRZRVRKNMY-ZUUMSKAQSA-N

> <FORMULA>
C28H34O16

> <MOLECULAR_WEIGHT>
626.564

> <EXACT_MASS>
626.184685015

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
58.09489212218931

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-{[(2S,3R,4S,5S,6R)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxybenzoate

> <JCHEM_LOGP>
-0.6545108440000011

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.081094469134785

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.732943413321102

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092344897183

> <JCHEM_POLAR_SURFACE_AREA>
251.35999999999996

> <JCHEM_REFRACTIVITY>
142.07890000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-{[(2S,3R,4S,5S,6R)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxybenzoate

> <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  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      14.670  -6.930   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.338  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.672  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.005  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.005  -6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.672  -7.700   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      18.672  -9.240   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      20.005 -10.010   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      21.339  -9.240   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      22.673 -10.010   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      24.006  -9.240   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      24.006  -7.700   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      22.673 -11.550   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      24.006 -12.320   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      21.339 -12.320   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      21.339 -13.860   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      20.005 -11.550   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      18.672 -12.320   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   43                                                  
CONECT    6    5    7   37                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    8   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   35                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   26   36                                                  
CONECT   36   35                                                            
CONECT   37    6   38                                                       
CONECT   38   37   39   41                                                  
CONECT   39   38   40                                                       
CONECT   40   39                                                            
CONECT   41   38   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41    5   44                                                  
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   94    0
END

View in JSmol

Synonyms

Value	Source
2-(2-O-Acetyl-b-D-glucopyranosyloxy)-6-hydroxybenzoate 2-(b-D-glucopyranosyloxy)benzyl ester	Generator
2-(2-O-Acetyl-b-D-glucopyranosyloxy)-6-hydroxybenzoic acid 2-(b-D-glucopyranosyloxy)benzyl ester	Generator
2-(2-O-Acetyl-beta-D-glucopyranosyloxy)-6-hydroxybenzoate 2-(beta-D-glucopyranosyloxy)benzyl ester	Generator
2-(2-O-Acetyl-β-D-glucopyranosyloxy)-6-hydroxybenzoate 2-(β-D-glucopyranosyloxy)benzyl ester	Generator
2-(2-O-Acetyl-β-D-glucopyranosyloxy)-6-hydroxybenzoic acid 2-(β-D-glucopyranosyloxy)benzyl ester	Generator

Chemical Formula

C₂₈H₃₄O₁₆

Average Mass

626.5640 Da

Monoisotopic Mass

626.18469 Da

IUPAC Name

(2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-{[(2S,3R,4S,5S,6R)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxybenzoate

Traditional Name

(2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-{[(2S,3R,4S,5S,6R)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxybenzoate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC(O)=C1C(=O)OCC1=CC=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C28H34O16/c1-12(31)40-25-23(36)21(34)18(10-30)44-28(25)42-16-8-4-6-14(32)19(16)26(38)39-11-13-5-2-3-7-15(13)41-27-24(37)22(35)20(33)17(9-29)43-27/h2-8,17-18,20-25,27-30,32-37H,9-11H2,1H3/t17-,18-,20-,21-,22+,23+,24-,25-,27-,28-/m1/s1

InChI Key

KGTNCRZRVRKNMY-ZUUMSKAQSA-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
Viburnum cylindricum	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
O-hydroxybenzoic acid ester
O-glycosyl compound
Benzyloxycarbonyl
Benzoate ester
Salicylic acid or derivatives
Benzoic acid or derivatives
Phenoxy compound
Phenol ether
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Sugar acid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Benzenoid
Vinylogous acid
Carboxylic acid ester
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Alcohol
Primary alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
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	-0.65	ChemAxon
pKa (Strongest Acidic)	9.73	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	251.36 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	142.08 m³·mol⁻¹	ChemAxon
Polarizability	58.09 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

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

101482750

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-{[(2s,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxybenzoate (NP0223375)

MOL for NP0223375 ((2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-{[(2s,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxybenzoate)

3D MOL for NP0223375 ((2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-{[(2s,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxybenzoate)

3D SDF for NP0223375 ((2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-{[(2s,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxybenzoate)

3D-SDF for NP0223375 ((2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-{[(2s,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxybenzoate)

PDB for NP0223375 ((2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-{[(2s,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxybenzoate)

3D PDB for NP0223375 ((2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-{[(2s,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxybenzoate)

SMILES for NP0223375 ((2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-{[(2s,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxybenzoate)

INCHI for NP0223375 ((2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-{[(2s,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxybenzoate)

Structure for NP0223375 ((2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-{[(2s,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxybenzoate)

3D Structure for NP0223375 ((2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl 2-{[(2s,3r,4s,5s,6r)-3-(acetyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxybenzoate)