NP-MRD: Showing NP-Card for methyl (4s,5r,6s)-4-{[(4r,5s)-4,5-dimethyl-1,3-dioxolan-2-yl]methyl}-5-ethenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate (NP0317078)

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Record Information

Version

2.0

Created at

2022-09-11 16:42:38 UTC

Updated at

2022-09-11 16:42:38 UTC

NP-MRD ID

NP0317078

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (4s,5r,6s)-4-{[(4r,5s)-4,5-dimethyl-1,3-dioxolan-2-yl]methyl}-5-ethenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate

Description

Loniceracetalide A belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. methyl (4s,5r,6s)-4-{[(4r,5s)-4,5-dimethyl-1,3-dioxolan-2-yl]methyl}-5-ethenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate is found in Lonicera japonica. Based on a literature review very few articles have been published on Loniceracetalide A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112218422D          

 32 34  0  0  1  0            999 V2000
   -1.3222   -4.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078   -3.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078   -2.9491    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3222   -2.5366    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0367   -2.9491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512   -2.5366    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4656   -2.9491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1801   -2.5366    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8946   -2.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6091   -2.5366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1801   -1.7116    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8946   -1.2991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4656   -1.2991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4656   -0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512   -1.7116    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0367   -1.2991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222   -1.7116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067   -1.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356   -1.7116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212   -0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067   -2.5366    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8212   -2.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212   -3.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4886   -4.2590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2337   -5.0437    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7186   -5.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4087   -5.0437    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0762   -5.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1537   -4.2590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  1  0  0  0
  4 17  1  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
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 24  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 26 32  1  0  0  0  0
M  END

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
   -0.4411   -0.8202   -3.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2218   -0.0858   -2.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0732    0.0933   -0.8829 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2891   -0.6271   -0.3543 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8778    0.2277    0.5810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1674    0.6026    0.2643 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3273    1.9593    0.1272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5762    2.3738   -0.2061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0350    3.5126    0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3153    3.8752    0.3181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6463    1.3663   -0.3384 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8342    0.9938   -1.6897 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5272    0.1605    0.5355 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5909   -0.0282    1.3963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1839    0.1343    1.2796 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9295   -1.1357    1.7629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8852   -1.8500    0.3100 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2014   -2.5354   -0.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3311   -1.7836   -0.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4622   -2.4850   -0.9894 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5394   -1.9434   -1.2759 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4228   -3.8680   -1.2459 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5342   -4.5574   -1.7873 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1331   -0.4108   -0.0921 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1609    0.5834    0.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0999    0.3936    1.2746 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0187    1.4727    1.2893 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1288    1.0015    0.5765 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3901    1.7525    0.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1847   -0.4404    1.0493 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0480   -0.5700    2.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8725   -0.7037    1.3272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1018   -0.8594   -4.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3054   -1.3782   -2.8383 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1007    0.4609   -2.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1142    1.1971   -0.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9907   -0.8161   -1.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4356    0.1197   -0.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4854    2.8830   -1.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3564    4.3576    0.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0446    3.2039    1.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8534    4.0827    1.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6250    1.8606   -0.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8633    1.7957   -2.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4805   -0.7404   -0.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1256   -0.8193    1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2816    0.8779    2.0978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7123   -1.3830    2.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2277   -3.5904   -0.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9780   -5.1845   -0.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1247   -5.2977   -2.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2395   -3.9275   -2.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6319   -0.4773    0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7348    0.8929   -0.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119    1.5540    0.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5475    0.5419    2.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9864    1.0757   -0.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4706    2.6608    0.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2600    1.1178    0.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4381    2.0675    1.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6354   -1.0559    0.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6818    0.1331    3.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1098   -0.3929    2.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9466   -1.6185    2.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 20  1  0
 20 21  2  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  3 24  1  0
 24 25  1  0
 25 26  1  0
 26 32  1  0
 32 30  1  0
 30 31  1  0
 30 28  1  0
 28 29  1  0
 28 27  1  0
 24 19  1  0
 27 26  1  0
 15  6  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
 18 49  1  0
  4 37  1  6
  6 38  1  6
  8 39  1  6
  9 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  1
 12 44  1  0
 13 45  1  6
 14 46  1  0
 15 47  1  1
 16 48  1  0
  3 36  1  6
  2 35  1  0
  1 33  1  0
  1 34  1  0
 24 53  1  1
 25 54  1  0
 25 55  1  0
 26 56  1  1
 30 61  1  6
 31 62  1  0
 31 63  1  0
 31 64  1  0
 28 57  1  6
 29 58  1  0
 29 59  1  0
 29 60  1  0
M  END


  Mrv1652309112218422D          

 32 34  0  0  1  0            999 V2000
   -1.3222   -4.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078   -3.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078   -2.9491    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3222   -2.5366    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0367   -2.9491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512   -2.5366    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4656   -2.9491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1801   -2.5366    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8946   -2.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6091   -2.5366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1801   -1.7116    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8946   -1.2991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4656   -1.2991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4656   -0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512   -1.7116    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0367   -1.2991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222   -1.7116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067   -1.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356   -1.7116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212   -0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067   -2.5366    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8212   -2.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212   -3.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4886   -4.2590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2337   -5.0437    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7186   -5.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4087   -5.0437    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0762   -5.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1537   -4.2590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  1  0  0  0
  4 17  1  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
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 24  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 26 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0317078

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](C=C)[C@@H]1CC1O[C@H](C)[C@H](C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O11/c1-5-11-12(6-15-29-9(2)10(3)30-15)13(19(26)27-4)8-28-20(11)32-21-18(25)17(24)16(23)14(7-22)31-21/h5,8-12,14-18,20-25H,1,6-7H2,2-4H3/t9-,10+,11-,12+,14-,15?,16-,17+,18-,20+,21+/m1/s1

> <INCHI_KEY>
FYLXQAYYBFZLSK-NQMWKHINSA-N

> <FORMULA>
C21H32O11

> <MOLECULAR_WEIGHT>
460.476

> <EXACT_MASS>
460.19446185

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
46.55890203044794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2S,3R,4S)-4-{[(4R,5S)-4,5-dimethyl-1,3-dioxolan-2-yl]methyl}-3-ethenyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

> <JCHEM_LOGP>
-0.29281909333333267

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.198719032298822

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.207016193590846

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847615592513

> <JCHEM_POLAR_SURFACE_AREA>
153.36999999999998

> <JCHEM_REFRACTIVITY>
107.22059999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4S,5R,6S)-4-{[(4R,5S)-4,5-dimethyl-1,3-dioxolan-2-yl]methyl}-5-ethenyl-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.468  -7.815   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.134  -7.045   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.134  -5.505   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.468  -4.735   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.802  -5.505   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -5.136  -4.735   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.469  -5.505   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -7.803  -4.735   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.137  -5.505   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0     -10.470  -4.735   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -7.803  -3.195   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -9.137  -2.425   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -6.469  -2.425   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -6.469  -0.885   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.136  -3.195   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.802  -2.425   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.468  -3.195   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.134  -2.425   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.199  -3.195   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.533  -2.425   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.867  -3.195   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.533  -0.885   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.867  -0.115   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.199  -4.735   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.533  -5.505   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.533  -7.045   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.779  -7.950   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.303  -9.415   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.208 -10.661   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.763  -9.415   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.142 -10.661   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.287  -7.950   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16                                                  
CONECT   16   15                                                            
CONECT   17    4   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22                                                            
CONECT   24   19    3   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   26                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
Loniceracetalide b	MeSH

Chemical Formula

C₂₁H₃₂O₁₁

Average Mass

460.4760 Da

Monoisotopic Mass

460.19446 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](C=C)[C@@H]1CC1O[C@H](C)[C@H](C)O1

InChI Identifier

InChI=1S/C21H32O11/c1-5-11-12(6-15-29-9(2)10(3)30-15)13(19(26)27-4)8-28-20(11)32-21-18(25)17(24)16(23)14(7-22)31-21/h5,8-12,14-18,20-25H,1,6-7H2,2-4H3/t9-,10+,11-,12+,14-,15?,16-,17+,18-,20+,21+/m1/s1

InChI Key

FYLXQAYYBFZLSK-NQMWKHINSA-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
Lonicera japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Glycosyl compound
Secoiridoid-skeleton
O-glycosyl compound
Monocyclic monoterpenoid
Monoterpenoid
Sugar acid
Monosaccharide
Oxane
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Enoate ester
Methyl ester
Meta-dioxolane
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Acetal
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00037434

Chemspider ID

553440

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

637857

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (4s,5r,6s)-4-{[(4r,5s)-4,5-dimethyl-1,3-dioxolan-2-yl]methyl}-5-ethenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate (NP0317078)

MOL for NP0317078 (methyl (4s,5r,6s)-4-{[(4r,5s)-4,5-dimethyl-1,3-dioxolan-2-yl]methyl}-5-ethenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D MOL for NP0317078 (methyl (4s,5r,6s)-4-{[(4r,5s)-4,5-dimethyl-1,3-dioxolan-2-yl]methyl}-5-ethenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D SDF for NP0317078 (methyl (4s,5r,6s)-4-{[(4r,5s)-4,5-dimethyl-1,3-dioxolan-2-yl]methyl}-5-ethenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D-SDF for NP0317078 (methyl (4s,5r,6s)-4-{[(4r,5s)-4,5-dimethyl-1,3-dioxolan-2-yl]methyl}-5-ethenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

PDB for NP0317078 (methyl (4s,5r,6s)-4-{[(4r,5s)-4,5-dimethyl-1,3-dioxolan-2-yl]methyl}-5-ethenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D PDB for NP0317078 (methyl (4s,5r,6s)-4-{[(4r,5s)-4,5-dimethyl-1,3-dioxolan-2-yl]methyl}-5-ethenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

SMILES for NP0317078 (methyl (4s,5r,6s)-4-{[(4r,5s)-4,5-dimethyl-1,3-dioxolan-2-yl]methyl}-5-ethenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

INCHI for NP0317078 (methyl (4s,5r,6s)-4-{[(4r,5s)-4,5-dimethyl-1,3-dioxolan-2-yl]methyl}-5-ethenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

Structure for NP0317078 (methyl (4s,5r,6s)-4-{[(4r,5s)-4,5-dimethyl-1,3-dioxolan-2-yl]methyl}-5-ethenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D Structure for NP0317078 (methyl (4s,5r,6s)-4-{[(4r,5s)-4,5-dimethyl-1,3-dioxolan-2-yl]methyl}-5-ethenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)