NP-MRD: Showing NP-Card for methyl (4s,5s,6s)-5-[(1s)-1-(acetyloxy)ethyl]-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate (NP0287805)

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Record Information

Version

2.0

Created at

2022-09-09 17:12:51 UTC

Updated at

2022-09-09 17:12:51 UTC

NP-MRD ID

NP0287805

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (4s,5s,6s)-5-[(1s)-1-(acetyloxy)ethyl]-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate

Description

Diderroside methyl ester 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,5s,6s)-5-[(1s)-1-(acetyloxy)ethyl]-4-(2-methoxy-2-oxoethyl)-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 Calycophyllum spruceanum. Based on a literature review very few articles have been published on Diderroside methyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092219122D          

 33 34  0  0  1  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1994   -0.5701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  1  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  2  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   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  1  0  0  0
 14 27  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
M  END

     RDKit          3D

 63 64  0  0  0  0  0  0  0  0999 V2000
   -1.9601    5.1883    0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6174    3.9988   -0.3216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9929    2.7984   -0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7505    2.7401   -0.4789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7580    1.5716   -0.8970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9240    0.3724   -1.0096 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5583   -0.8160   -1.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9276   -0.9262   -2.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7433    0.0102   -1.9155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3758   -2.1039   -2.6416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7142   -2.2796   -3.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6927   -1.8415   -1.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3892   -1.6908   -1.3961 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0266   -0.9096   -0.2992 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0370   -0.0518   -0.6940 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2244   -0.2133    0.0237 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5687    1.0271    0.5134 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8417    1.1298    1.0176 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5750    2.2180    0.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8694    3.4059    0.4048 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6493   -0.1304    0.9674 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1931   -1.0456    1.9358 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6403   -0.7629   -0.4001 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6158   -0.1599   -1.1914 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2686   -0.6277   -1.0030 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8524   -1.8378   -1.5681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1575   -0.0546    0.2130 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9414   -0.8399    1.2109 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1106   -0.0880    1.7716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1326   -1.2508    2.3158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8857   -2.5684    2.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0440   -2.9811    3.7925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3963   -3.4641    1.9342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1819    5.9385   -0.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4213    5.5729    0.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8558    5.0637    0.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2903    1.7958   -1.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6101    1.5470   -0.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0901    0.6470   -1.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4108   -1.7089   -2.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0188   -3.3518   -3.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7906   -1.9551   -4.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0563   -2.7631   -2.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3134   -1.5893    0.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1410   -1.0057    0.7884 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8436    1.4738    2.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5966    1.9123   -0.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5940    2.3125    0.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3311    4.1302   -0.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7137    0.1509    1.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5670   -1.9342    1.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9249   -1.8404   -0.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3978   -0.2848   -2.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2935    0.1420   -1.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4955   -2.1553   -2.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7035    0.8254    0.6797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2740   -1.8193    0.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0433   -0.2491    1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8415    0.9697    1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3124   -0.4652    2.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8407   -2.3127    3.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2277   -4.0402    3.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6700   -2.8236    4.7133 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 27 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 14 13  1  0
 13 12  1  0
 12  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
  7  6  1  0
 25 16  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  6
 27 56  1  1
 28 57  1  6
 29 58  1  0
 29 59  1  0
 29 60  1  0
 32 61  1  0
 32 62  1  0
 32 63  1  0
 14 44  1  1
 16 45  1  1
 18 46  1  1
 19 47  1  0
 19 48  1  0
 20 49  1  0
 21 50  1  1
 22 51  1  0
 23 52  1  1
 24 53  1  0
 25 54  1  6
 26 55  1  0
 12 43  1  0
 11 40  1  0
 11 41  1  0
 11 42  1  0
M  END


  Mrv1652309092219122D          

 33 34  0  0  1  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1994   -0.5701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  1  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  2  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   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  1  0  0  0
 14 27  1  0  0  0  0
  6 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0287805

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H]1[C@@H]([C@H](C)OC(C)=O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C1C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O13/c1-8(31-9(2)22)14-10(5-13(23)28-3)11(18(27)29-4)7-30-19(14)33-20-17(26)16(25)15(24)12(6-21)32-20/h7-8,10,12,14-17,19-21,24-26H,5-6H2,1-4H3/t8-,10+,12+,14+,15+,16-,17+,19-,20-/m0/s1

> <INCHI_KEY>
GHGFDNVEGGUXDM-XDZSTEIDSA-N

> <FORMULA>
C20H30O13

> <MOLECULAR_WEIGHT>
478.447

> <EXACT_MASS>
478.168641026

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
45.57117643068263

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S,3S,4S)-3-[(1S)-1-(acetyloxy)ethyl]-4-(2-methoxy-2-oxoethyl)-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>
-1.8439206006666677

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.198724323815451

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.207029971791794

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981084760188039

> <JCHEM_POLAR_SURFACE_AREA>
187.51

> <JCHEM_REFRACTIVITY>
104.70820000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4S,5S,6S)-5-[(1S)-1-(acetyloxy)ethyl]-4-(2-methoxy-2-oxoethyl)-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                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.239  -1.064   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   27                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10                                                            
CONECT   12    7   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   16   26                                                  
CONECT   26   25                                                            
CONECT   27   14    6   28                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₁₃

Average Mass

478.4470 Da

Monoisotopic Mass

478.16864 Da

IUPAC Name

methyl (2S,3S,4S)-3-[(1S)-1-(acetyloxy)ethyl]-4-(2-methoxy-2-oxoethyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

Traditional Name

methyl (4S,5S,6S)-5-[(1S)-1-(acetyloxy)ethyl]-4-(2-methoxy-2-oxoethyl)-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@H]1[C@@H]([C@H](C)OC(C)=O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C1C(=O)OC

InChI Identifier

InChI=1S/C20H30O13/c1-8(31-9(2)22)14-10(5-13(23)28-3)11(18(27)29-4)7-30-19(14)33-20-17(26)16(25)15(24)12(6-21)32-20/h7-8,10,12,14-17,19-21,24-26H,5-6H2,1-4H3/t8-,10+,12+,14+,15+,16-,17+,19-,20-/m0/s1

InChI Key

GHGFDNVEGGUXDM-XDZSTEIDSA-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
Calycophyllum spruceanum	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
Tricarboxylic acid or derivatives
Sugar acid
Monosaccharide
Oxane
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Carbonyl group
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
logP	-1.8	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	187.51 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	104.71 m³·mol⁻¹	ChemAxon
Polarizability	45.57 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28944701

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101756906

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,5s,6s)-5-[(1s)-1-(acetyloxy)ethyl]-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate (NP0287805)

MOL for NP0287805 (methyl (4s,5s,6s)-5-[(1s)-1-(acetyloxy)ethyl]-4-(2-methoxy-2-oxoethyl)-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 NP0287805 (methyl (4s,5s,6s)-5-[(1s)-1-(acetyloxy)ethyl]-4-(2-methoxy-2-oxoethyl)-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 NP0287805 (methyl (4s,5s,6s)-5-[(1s)-1-(acetyloxy)ethyl]-4-(2-methoxy-2-oxoethyl)-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 NP0287805 (methyl (4s,5s,6s)-5-[(1s)-1-(acetyloxy)ethyl]-4-(2-methoxy-2-oxoethyl)-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 NP0287805 (methyl (4s,5s,6s)-5-[(1s)-1-(acetyloxy)ethyl]-4-(2-methoxy-2-oxoethyl)-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 NP0287805 (methyl (4s,5s,6s)-5-[(1s)-1-(acetyloxy)ethyl]-4-(2-methoxy-2-oxoethyl)-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 NP0287805 (methyl (4s,5s,6s)-5-[(1s)-1-(acetyloxy)ethyl]-4-(2-methoxy-2-oxoethyl)-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 NP0287805 (methyl (4s,5s,6s)-5-[(1s)-1-(acetyloxy)ethyl]-4-(2-methoxy-2-oxoethyl)-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 NP0287805 (methyl (4s,5s,6s)-5-[(1s)-1-(acetyloxy)ethyl]-4-(2-methoxy-2-oxoethyl)-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 NP0287805 (methyl (4s,5s,6s)-5-[(1s)-1-(acetyloxy)ethyl]-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)