NP-MRD: Showing NP-Card for (2r,3s,4r,5r,6s)-6-(2-acetyl-5-methoxyphenoxy)-4,5-dihydroxy-2-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-3-yl 3,4,5-trihydroxybenzoate (NP0269841)

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Record Information

Version

2.0

Created at

2022-09-08 15:27:07 UTC

Updated at

2022-09-08 15:27:08 UTC

NP-MRD ID

NP0269841

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4r,5r,6s)-6-(2-acetyl-5-methoxyphenoxy)-4,5-dihydroxy-2-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-3-yl 3,4,5-trihydroxybenzoate

Description

Suffruticoside D belongs to the class of organic compounds known as tannins. These are naturally occurring polyphenols which be categorized into four main classes: Hydrolyzable tannin (based on ellagic acid or gallic acid), condensed tannins (made of oligomeric or polymeric proanthocyanidins), complex tannins (made of a catechin bound to a gallotannin or elagitannin), and phlorotannins (oligomers of phloroglucinol). (2r,3s,4r,5r,6s)-6-(2-acetyl-5-methoxyphenoxy)-4,5-dihydroxy-2-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-3-yl 3,4,5-trihydroxybenzoate is found in Paeonia suffruticosa. Based on a literature review very few articles have been published on Suffruticoside D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082217272D          

 43 46  0  0  1  0            999 V2000
    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
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    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
    2.1434   -6.1875    0.0000 C   0  0  0  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   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -8.6625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -7.8375    0.0000 C   0  0  2  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
   -2.8579   -7.4250    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
   -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
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -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
    0.0000   -4.1250    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
    2.1434   -5.3625    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  1  0  0  0
 14 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 30 38  1  0  0  0  0
 26 39  1  0  0  0  0
 39 40  1  6  0  0  0
 39 41  1  0  0  0  0
 12 41  1  0  0  0  0
 41 42  1  1  0  0  0
 10 43  2  0  0  0  0
  3 43  1  0  0  0  0
M  END

     RDKit          3D

 75 78  0  0  0  0  0  0  0  0999 V2000
   -7.6695    0.3986    3.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4945    0.1753    2.7049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2490    0.6489    1.4258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2017    1.3979    0.7704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9239    1.8610   -0.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7267    1.5875   -1.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4834    2.0937   -2.4927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4854    2.9048   -3.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3953    1.8597   -3.0996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7686    0.8296   -0.4764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5976    0.5643   -1.0943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4877   -0.1477   -0.6838 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3266    0.6309   -0.5984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3615   -0.1440    0.0039 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7103    0.6237    0.7039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4342    1.4720   -0.0929 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2390    3.4998    0.6879 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9711    4.0279    1.7422 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4432    3.7286    1.6464 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1045    4.5222    0.7208 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7208    2.2822    1.3335 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0495    2.1168    1.0042 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7979    1.8317    0.2062 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0212    0.5115   -0.0957 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1389   -1.1400   -0.9992 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1962   -1.9347   -0.5313 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3621   -2.0241   -1.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4289   -1.3808   -2.3594 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5007   -2.8256   -0.8616 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4974   -3.5526    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5884   -4.3117    0.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5894   -5.0400    1.8537 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7373   -4.3532   -0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8164   -5.1249    0.2963 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7600   -3.6365   -1.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8759   -3.6565   -2.0978 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6418   -2.8912   -1.6241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0250   -2.0974   -1.2771 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7259   -2.9877   -2.2762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2923   -1.3501   -1.5737 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3593   -2.2327   -1.2935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0409    0.3754    0.7878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5335    1.3194    4.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7791   -0.4435    4.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5840    0.4518    2.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1635    1.6475    1.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6923    2.4436   -1.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2580    2.2545   -3.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9802    3.5546   -3.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0318    3.5887   -2.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6558   -0.5396    0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8954   -0.7418    0.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4033   -0.1151    1.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5820    3.6496    2.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8872    3.9517    2.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5470    4.6952   -0.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4560    1.6692    2.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3708    2.8537    0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0080    2.4363   -0.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4005   -0.6520   -1.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6201   -3.5237    0.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3898   -5.5785    2.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7230   -4.1627   -1.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7031   -2.3380   -2.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1670   -2.6638   -0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  6 10  1  0
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 41 12  1  0
 24 17  1  0
 38 30  1  0
  1 44  1  0
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  4 47  1  0
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  8 50  1  0
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 31 66  1  0
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 35 68  1  0
 37 69  1  0
 38 70  1  0
 39 71  1  1
 40 72  1  0
 41 73  1  6
 42 74  1  0
 43 75  1  0
M  END


  Mrv1652309082217272D          

 43 46  0  0  1  0            999 V2000
    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
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -7.8375    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
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    1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1434   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5724   -8.6625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.5724   -7.8375    0.0000 C   0  0  2  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
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   -2.8579   -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
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -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
    0.0000   -4.1250    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
    2.1434   -5.3625    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  1  0  0  0
 14 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 30 38  1  0  0  0  0
 26 39  1  0  0  0  0
 39 40  1  6  0  0  0
 39 41  1  0  0  0  0
 12 41  1  0  0  0  0
 41 42  1  1  0  0  0
 10 43  2  0  0  0  0
  3 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0269841

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C(C)=O)C(O[C@@H]2O[C@H](CO[C@@H]3OC[C@H](O)[C@H](O)[C@H]3O)[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O)[C@H]2O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O16/c1-10(28)13-4-3-12(38-2)7-17(13)41-27-23(36)21(34)24(43-25(37)11-5-14(29)19(32)15(30)6-11)18(42-27)9-40-26-22(35)20(33)16(31)8-39-26/h3-7,16,18,20-24,26-27,29-36H,8-9H2,1-2H3/t16-,18+,20-,21+,22+,23+,24+,26-,27+/m0/s1

> <INCHI_KEY>
RUAYDWCAPDNACJ-NFEAGSSZSA-N

> <FORMULA>
C27H32O16

> <MOLECULAR_WEIGHT>
612.537

> <EXACT_MASS>
612.16903495

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
58.189575790290384

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4R,5R,6S)-6-(2-acetyl-5-methoxyphenoxy)-4,5-dihydroxy-2-({[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-3-yl 3,4,5-trihydroxybenzoate

> <JCHEM_LOGP>
-0.7543081659999996

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.20170607912234

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.103126889597176

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5265804040847843

> <JCHEM_POLAR_SURFACE_AREA>
251.35999999999996

> <JCHEM_REFRACTIVITY>
139.26480000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4R,5R,6S)-6-(2-acetyl-5-methoxyphenoxy)-4,5-dihydroxy-2-({[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-3-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.000 -12.320   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667 -13.860   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.668 -16.170   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -8.002 -16.940   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -8.002 -13.860   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   43                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6   11   43                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   41                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   26                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   17   25                                                  
CONECT   25   24                                                            
CONECT   26   14   27   39                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   38                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   30                                                       
CONECT   39   26   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   12   42                                                  
CONECT   42   41                                                            
CONECT   43   10    3                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₁₆

Average Mass

612.5370 Da

Monoisotopic Mass

612.16903 Da

IUPAC Name

(2R,3S,4R,5R,6S)-6-(2-acetyl-5-methoxyphenoxy)-4,5-dihydroxy-2-({[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-3-yl 3,4,5-trihydroxybenzoate

Traditional Name

(2R,3S,4R,5R,6S)-6-(2-acetyl-5-methoxyphenoxy)-4,5-dihydroxy-2-({[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-3-yl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C(C)=O)C(O[C@@H]2O[C@H](CO[C@@H]3OC[C@H](O)[C@H](O)[C@H]3O)[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O)[C@H]2O)=C1

InChI Identifier

InChI=1S/C27H32O16/c1-10(28)13-4-3-12(38-2)7-17(13)41-27-23(36)21(34)24(43-25(37)11-5-14(29)19(32)15(30)6-11)18(42-27)9-40-26-22(35)20(33)16(31)8-39-26/h3-7,16,18,20-24,26-27,29-36H,8-9H2,1-2H3/t16-,18+,20-,21+,22+,23+,24+,26-,27+/m0/s1

InChI Key

RUAYDWCAPDNACJ-NFEAGSSZSA-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
Paeonia suffruticosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tannins. These are naturally occurring polyphenols which be categorized into four main classes: Hydrolyzable tannin (based on ellagic acid or gallic acid), condensed tannins (made of oligomeric or polymeric proanthocyanidins), complex tannins (made of a catechin bound to a gallotannin or elagitannin), and phlorotannins (oligomers of phloroglucinol).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Not Available

Direct Parent

Tannins

Alternative Parents

Substituents

Tannin
Phenolic glycoside
Galloyl ester
Alkyl-phenylketone
Gallic acid or derivatives
Glycosyl compound
O-glycosyl compound
P-hydroxybenzoic acid ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid alkyl ester
Disaccharide
Benzoate ester
Acetophenone
Phenylketone
Benzoic acid or derivatives
Pyrogallol derivative
Benzenetriol
Phenoxy compound
Benzoyl
Anisole
Phenol ether
Methoxybenzene
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Oxane
Monocyclic benzene moiety
Benzenoid
Ketone
Secondary alcohol
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Ether
Organic oxygen compound
Alcohol
Aldehyde
Organooxygen compound
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	-0.75	ChemAxon
pKa (Strongest Acidic)	8.1	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	251.36 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	139.26 m³·mol⁻¹	ChemAxon
Polarizability	58.19 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

C00033399

Chemspider ID

4479253

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5321547

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3s,4r,5r,6s)-6-(2-acetyl-5-methoxyphenoxy)-4,5-dihydroxy-2-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-3-yl 3,4,5-trihydroxybenzoate (NP0269841)

MOL for NP0269841 ((2r,3s,4r,5r,6s)-6-(2-acetyl-5-methoxyphenoxy)-4,5-dihydroxy-2-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

3D MOL for NP0269841 ((2r,3s,4r,5r,6s)-6-(2-acetyl-5-methoxyphenoxy)-4,5-dihydroxy-2-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

3D SDF for NP0269841 ((2r,3s,4r,5r,6s)-6-(2-acetyl-5-methoxyphenoxy)-4,5-dihydroxy-2-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

3D-SDF for NP0269841 ((2r,3s,4r,5r,6s)-6-(2-acetyl-5-methoxyphenoxy)-4,5-dihydroxy-2-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

PDB for NP0269841 ((2r,3s,4r,5r,6s)-6-(2-acetyl-5-methoxyphenoxy)-4,5-dihydroxy-2-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

3D PDB for NP0269841 ((2r,3s,4r,5r,6s)-6-(2-acetyl-5-methoxyphenoxy)-4,5-dihydroxy-2-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

SMILES for NP0269841 ((2r,3s,4r,5r,6s)-6-(2-acetyl-5-methoxyphenoxy)-4,5-dihydroxy-2-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

INCHI for NP0269841 ((2r,3s,4r,5r,6s)-6-(2-acetyl-5-methoxyphenoxy)-4,5-dihydroxy-2-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

Structure for NP0269841 ((2r,3s,4r,5r,6s)-6-(2-acetyl-5-methoxyphenoxy)-4,5-dihydroxy-2-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

3D Structure for NP0269841 ((2r,3s,4r,5r,6s)-6-(2-acetyl-5-methoxyphenoxy)-4,5-dihydroxy-2-({[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-3-yl 3,4,5-trihydroxybenzoate)