NP-MRD: Showing NP-Card for methyl (1s,4as,5s,6r,7r,7ar)-5,6-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate (NP0254900)

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Record Information

Version

2.0

Created at

2022-09-07 19:12:42 UTC

Updated at

2022-09-07 19:12:42 UTC

NP-MRD ID

NP0254900

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1s,4as,5s,6r,7r,7ar)-5,6-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate

Description

Arbortristoside E belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. methyl (1s,4as,5s,6r,7r,7ar)-5,6-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate is found in Nyctanthes arbor-tristis. Based on a literature review very few articles have been published on Arbortristoside E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072221122D          

 40 43  0  0  1  0            999 V2000
    4.7079    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9947   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7092   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4236   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1381   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1381   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8526   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5671   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4236   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7092   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1368   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2789   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    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
  3  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
  8  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 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  2  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  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 19 26  1  0  0  0  0
 12 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 10 31  1  0  0  0  0
 31 32  1  1  0  0  0
  8 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34  5  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 33 39  1  0  0  0  0
 39 40  1  1  0  0  0
M  END

     RDKit          3D

 74 77  0  0  0  0  0  0  0  0999 V2000
   -9.4199   -1.1232   -2.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1011   -1.3873   -1.8106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2160   -0.3491   -1.5604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6160    0.8142   -1.7837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8629   -0.5478   -1.0570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4006   -1.7767   -0.8072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1218   -1.9249   -0.3343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2181   -0.8852   -0.0534 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9412   -1.3608   -0.3111 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1863   -1.3297    0.8562 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0693   -0.4736    0.6800 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2315   -0.0466    1.9869 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1482    1.1072    2.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3784    1.0628    1.4645 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4950    0.3469    1.6268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5354   -0.5243    2.5171 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7824   -0.1762    0.9735 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0153   -0.0579    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1814    0.8402   -0.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3840    0.9190   -1.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4457    0.0957   -1.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6522    0.1485   -1.9218 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8817    1.0343   -2.9698 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2734   -0.8027   -0.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0860   -0.8779    0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4207   -1.1844    2.9228 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7262   -1.3522    3.7698 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4982   -2.5201    2.1913 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6730   -2.7307    1.5238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6286   -2.6900    1.2037 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5881   -3.5073    1.8010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5449    0.3650   -0.8707 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0124    0.6299   -0.8273 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2273    1.2411    0.5409 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3321    2.1043    0.5408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9618    1.9637    0.8763 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1558    3.3240    0.8694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9684    1.6002   -0.2128 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9972    2.7287   -1.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1527   -1.7220   -1.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4582   -1.4581   -3.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6927   -0.0503   -2.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0754   -2.6159   -0.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3441   -0.5860    1.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8337   -0.9297    1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7993    0.4019    2.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5942    1.9846    1.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1822    1.4281    3.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7015    1.2815    0.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7255   -0.9203    1.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3803    1.4939   -1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5165    1.6233   -2.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9471    2.0687   -2.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8909    0.8281   -3.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0930    1.0751   -3.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1121   -1.4616    0.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9558   -1.5937    1.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2442   -1.1258    3.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0601   -0.4117    3.8845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4434   -3.2981    3.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5672   -3.0655    0.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2790   -3.1436    0.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1626   -2.9020    2.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1450    0.2688   -1.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2464    1.3677   -1.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4443    0.4129    1.2425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6413    2.1410    1.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5615    1.5694    1.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9767    3.6223    1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9614    1.4578    0.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4166    3.5761   -0.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5402    2.4174   -2.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0555    3.0354   -1.3438 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
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 17 18  2  0
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 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
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 12 27  1  0
 27 28  1  0
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 29 30  1  0
 29 31  1  0
 31 32  1  0
  8 33  1  0
 33 39  1  0
 39 40  1  0
 39 37  1  0
 37 38  1  0
 37 35  1  0
 35 36  1  0
 35 34  1  0
 34  5  1  0
 31 10  1  0
 34 33  1  0
 26 19  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  6 44  1  0
  8 45  1  1
 10 46  1  1
 12 47  1  1
 13 48  1  0
 13 49  1  0
 17 50  1  0
 18 51  1  0
 20 52  1  0
 21 53  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
 26 58  1  0
 27 59  1  1
 28 60  1  0
 29 61  1  1
 30 62  1  0
 31 63  1  6
 32 64  1  0
 33 65  1  6
 39 71  1  1
 40 72  1  0
 40 73  1  0
 40 74  1  0
 37 69  1  1
 38 70  1  0
 35 67  1  1
 36 68  1  0
 34 66  1  6
M  END


  Mrv1652309072221122D          

 40 43  0  0  1  0            999 V2000
    4.7079    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2802   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9947   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7092   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4236   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1381   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1381   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8526   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5671   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4236   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7092   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1368   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2789   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    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
  3  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
  8  9  1  1  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 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  2  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  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 19 26  1  0  0  0  0
 12 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 10 31  1  0  0  0  0
 31 32  1  1  0  0  0
  8 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34  5  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 33 39  1  0  0  0  0
 39 40  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0254900

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](COC(=O)\C=C\C3=CC=C(OC)C=C3)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]2[C@@H](C)[C@@H](O)[C@@H](O)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O13/c1-12-18-19(22(31)20(12)29)15(25(34)36-3)10-38-26(18)40-27-24(33)23(32)21(30)16(39-27)11-37-17(28)9-6-13-4-7-14(35-2)8-5-13/h4-10,12,16,18-24,26-27,29-33H,11H2,1-3H3/b9-6+/t12-,16-,18-,19-,20-,21-,22+,23+,24-,26+,27+/m1/s1

> <INCHI_KEY>
BFVPQNASGKMXJQ-WBDYHHAWSA-N

> <FORMULA>
C27H34O13

> <MOLECULAR_WEIGHT>
566.556

> <EXACT_MASS>
566.199941155

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
57.01008520228392

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,4aS,5S,6R,7R,7aR)-5,6-dihydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

> <JCHEM_LOGP>
0.042124111000000256

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.0775681667821

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.190787248890707

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2651115905225003

> <JCHEM_POLAR_SURFACE_AREA>
190.67

> <JCHEM_REFRACTIVITY>
134.78980000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,4aS,5S,6R,7R,7aR)-5,6-dihydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       8.788   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.454   4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.787   4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.454   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.788  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.122  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.455  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.789  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      14.123  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.123  -0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      15.456  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.790  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.124  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      19.457  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.791  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.791  -4.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      22.125  -5.390   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      23.458  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.457  -5.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.124  -4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.122  -4.620   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.455  -5.390   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.788  -5.390   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.788  -6.930   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       7.454  -4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.121  -5.390   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.846   3.481   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       0.877   0.770   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   34                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   33                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   31                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   27                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26                                                       
CONECT   26   25   19                                                       
CONECT   27   12   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   10   32                                                  
CONECT   32   31                                                            
CONECT   33    8   34   39                                                  
CONECT   34   33    5   35                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   33   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄O₁₃

Average Mass

566.5560 Da

Monoisotopic Mass

566.19994 Da

IUPAC Name

methyl (1S,4aS,5S,6R,7R,7aR)-5,6-dihydroxy-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](COC(=O)\C=C\C3=CC=C(OC)C=C3)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]2[C@@H](C)[C@@H](O)[C@@H](O)[C@H]12

InChI Identifier

InChI=1S/C27H34O13/c1-12-18-19(22(31)20(12)29)15(25(34)36-3)10-38-26(18)40-27-24(33)23(32)21(30)16(39-27)11-37-17(28)9-6-13-4-7-14(35-2)8-5-13/h4-10,12,16,18-24,26-27,29-33H,11H2,1-3H3/b9-6+/t12-,16-,18-,19-,20-,21-,22+,23+,24-,26+,27+/m1/s1

InChI Key

BFVPQNASGKMXJQ-WBDYHHAWSA-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
Nyctanthes arbor-tristis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Cinnamic acid ester
Cinnamic acid or derivatives
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Aromatic monoterpenoid
Bicyclic monoterpenoid
Monoterpenoid
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
Alkyl aryl ether
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Monosaccharide
Benzenoid
Dicarboxylic acid or derivatives
Oxane
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic alcohol
Methyl ester
Carboxylic acid ester
Secondary alcohol
Polyol
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Ether
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	0.042	ChemAxon
pKa (Strongest Acidic)	12.19	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	190.67 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	134.79 m³·mol⁻¹	ChemAxon
Polarizability	57.01 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

C00010487

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

14632884

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1s,4as,5s,6r,7r,7ar)-5,6-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate (NP0254900)

MOL for NP0254900 (methyl (1s,4as,5s,6r,7r,7ar)-5,6-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D MOL for NP0254900 (methyl (1s,4as,5s,6r,7r,7ar)-5,6-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D SDF for NP0254900 (methyl (1s,4as,5s,6r,7r,7ar)-5,6-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D-SDF for NP0254900 (methyl (1s,4as,5s,6r,7r,7ar)-5,6-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

PDB for NP0254900 (methyl (1s,4as,5s,6r,7r,7ar)-5,6-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D PDB for NP0254900 (methyl (1s,4as,5s,6r,7r,7ar)-5,6-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

SMILES for NP0254900 (methyl (1s,4as,5s,6r,7r,7ar)-5,6-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

INCHI for NP0254900 (methyl (1s,4as,5s,6r,7r,7ar)-5,6-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

Structure for NP0254900 (methyl (1s,4as,5s,6r,7r,7ar)-5,6-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)

3D Structure for NP0254900 (methyl (1s,4as,5s,6r,7r,7ar)-5,6-dihydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2e)-3-(4-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carboxylate)