NP-MRD: Showing NP-Card for Sempervirenoside A (NP0054009)

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Record Information

Version

2.0

Created at

2022-04-28 00:29:55 UTC

Updated at

2022-04-28 00:29:55 UTC

NP-MRD ID

NP0054009

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sempervirenoside A

Description

(2S,3S,4R,5R)-2-{[(2S,3S,4R,5S,6S)-3-(acetyloxy)-5-hydroxy-6-{[5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-7-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-3-yl]oxy}-2-methyloxan-4-yl]oxy}-3,5-dihydroxyoxan-4-yl acetate belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Sempervirenoside A is found in Epimedium sempervirens. Based on a literature review very few articles have been published on (2S,3S,4R,5R)-2-{[(2S,3S,4R,5S,6S)-3-(acetyloxy)-5-hydroxy-6-{[5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-7-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-3-yl]oxy}-2-methyloxan-4-yl]oxy}-3,5-dihydroxyoxan-4-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202292D          

 63 68  0  0  1  0            999 V2000
   -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  0  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
    0.7145   -0.4125    0.0000 C   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
    0.0000    0.8250    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
   -0.7145    2.0625    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
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  2  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
    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 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  1  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
    3.5724   -5.3625    0.0000 O   0  0  0  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
    5.7158   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -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
    1.4289   -4.9500    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   -4.1250    0.0000 C   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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -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
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    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
  1  2  2  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
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  2  0  0  0  0
 14 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  1  0  0  0
 22 25  1  1  0  0  0
 26 25  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 29 32  1  6  0  0  0
 28 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 27 37  1  1  0  0  0
 21 38  1  1  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 20 42  1  6  0  0  0
 13 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 43 48  1  0  0  0  0
 46 49  1  0  0  0  0
 49 50  1  0  0  0  0
  3 51  1  0  0  0  0
  1 52  1  0  0  0  0
 53 52  1  1  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 53 58  1  0  0  0  0
 57 59  1  6  0  0  0
 59 60  1  0  0  0  0
 56 61  1  6  0  0  0
 55 62  1  1  0  0  0
 54 63  1  6  0  0  0
M  END

     RDKit          3D

115120  0  0  0  0  0  0  0  0999 V2000
   -0.1100   -5.0147   -5.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6505   -3.8598   -5.4476 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2494   -2.9092   -4.4866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8926   -3.0668   -3.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2771   -2.1213   -2.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5275   -0.9856   -2.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0377   -0.0118   -1.5842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3025   -0.1680   -1.1627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9045    0.6140   -0.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2223    0.3966    0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9457   -0.7862   -0.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0110   -1.8095    0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6743   -3.0671    0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8030   -3.9911    1.6637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1933   -3.7047   -0.7757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9153    1.1854    0.9734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1596    1.0933    1.4181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3257    0.4632    1.3894 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.3541    1.3996    1.0753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1304    2.6047    1.7352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.3996    3.4232    1.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2069    4.6368    2.3363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7244    2.3898    3.1738 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.4132    3.3237    3.9464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1251    1.0196    3.6710 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4333    0.8300    4.8843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7709   -0.0993    2.7624 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.9627   -0.8026    2.4794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1751    2.2779    1.4969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8793    2.5197    1.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1365    3.5796    1.6397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2474    1.6806    0.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9499    1.9043   -0.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2870    2.8490    0.2989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3463    1.0304   -1.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9880    1.2942   -1.4127 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0245    0.8294   -0.5540 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3377    1.9608    0.2462 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9364    1.5604    1.4328 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8616    1.2043    2.4179 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8112    0.3474    1.1579 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8332    0.2451    2.1494 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9077   -0.7673    3.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0404   -0.7272    4.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0293   -1.6578    3.0740 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3688    0.2977   -0.2250 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3867    1.1727   -0.4811 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6185    0.6195   -0.7282 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6072    1.0680    0.1152 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3340    2.1416   -0.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2222    1.8031   -1.4939 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4699    1.3328   -1.1043 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4916    0.8181   -2.4005 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8853   -0.4760   -1.9955 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5568   -1.3693   -2.8178 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9204   -2.7078   -2.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8461   -1.0357   -3.9936 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9943    0.9324   -2.1518 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6372    2.2523   -2.4176 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2479    0.3081   -1.2291 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5866    1.0351   -2.3722 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6076   -0.8384   -3.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0138   -1.7859   -4.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9620   -4.7824   -6.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5197   -5.5068   -4.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5236   -5.7372   -6.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5007   -3.9525   -3.9452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1889   -2.2655   -2.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8776   -0.5534   -0.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2877   -1.2255   -1.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3581   -1.4983    1.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0073   -5.0184    1.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6261   -3.5621    2.2642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8468   -3.8672    2.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0741   -3.7494   -0.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5960   -4.7513   -0.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4521   -3.1121   -1.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4949   -0.3840    0.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3451    3.1479    1.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2107    2.8424    2.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7181    3.5552    0.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8109    5.2792    1.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6523    2.5910    3.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1169    2.9112    4.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2110    1.0294    3.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9546    1.6342    5.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0660   -0.8272    3.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7075   -0.1442    2.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6318    2.9643    2.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5125    4.2469    2.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5860    0.0633    0.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282202292D          

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M  END
> <DATABASE_ID>
NP0054009

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@H](O[C@@H]3OC[C@@H](O)[C@@H](OC(C)=O)[C@@H]3O)[C@@H]2O)C(=O)C2=C(O)C=C(O[C@@H]3O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(CC=C(C)C)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C42H52O21/c1-16(2)7-12-22-25(59-41-31(51)30(50)28(48)26(14-43)60-41)13-23(46)27-29(49)38(35(61-36(22)27)20-8-10-21(54-6)11-9-20)63-42-33(53)39(34(17(3)56-42)57-18(4)44)62-40-32(52)37(58-19(5)45)24(47)15-55-40/h7-11,13,17,24,26,28,30-34,37,39-43,46-48,50-53H,12,14-15H2,1-6H3/t17-,24+,26-,28+,30-,31+,32-,33-,34-,37+,39+,40-,41+,42-/m0/s1

> <INCHI_KEY>
NKJJMKATLZNGPP-OSQVXMILSA-N

> <FORMULA>
C42H52O21

> <MOLECULAR_WEIGHT>
892.857

> <EXACT_MASS>
892.300108694

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
115

> <JCHEM_AVERAGE_POLARIZABILITY>
88.69654591715752

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4R,5S,6S)-4-{[(2S,3S,4R,5R)-4-(acetyloxy)-3,5-dihydroxyoxan-2-yl]oxy}-5-hydroxy-6-{[5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-7-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-3-yl]oxy}-2-methyloxan-3-yl acetate

> <ALOGPS_LOGP>
1.59

> <JCHEM_LOGP>
0.5537830713333315

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.797977906126604

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.068544862802265

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092344940455

> <JCHEM_POLAR_SURFACE_AREA>
305.34999999999997

> <JCHEM_REFRACTIVITY>
211.37419999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4R,5S,6S)-4-{[(2S,3S,4R,5R)-4-(acetyloxy)-3,5-dihydroxyoxan-2-yl]oxy}-5-hydroxy-6-{[5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-7-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-3-yl]oxy}-2-methyloxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   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  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       8.002 -13.860   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      10.669 -12.320   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      12.003 -14.630   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    6   52                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   51                                                  
CONECT    4    3    5   15                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    5   13                                                       
CONECT   13   12   14   43                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14    4   16                                                  
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   42                                                  
CONECT   21   20   22   38                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22   18   24                                                  
CONECT   24   23                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28   37                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30   26                                                       
CONECT   32   29                                                            
CONECT   33   28   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   27                                                            
CONECT   38   21   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   20                                                            
CONECT   43   13   44   48                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47   49                                                  
CONECT   47   46   48                                                       
CONECT   48   47   43                                                       
CONECT   49   46   50                                                       
CONECT   50   49                                                            
CONECT   51    3                                                            
CONECT   52    1   53                                                       
CONECT   53   52   54   58                                                  
CONECT   54   53   55   63                                                  
CONECT   55   54   56   62                                                  
CONECT   56   55   57   61                                                  
CONECT   57   56   58   59                                                  
CONECT   58   57   53                                                       
CONECT   59   57   60                                                       
CONECT   60   59                                                            
CONECT   61   56                                                            
CONECT   62   55                                                            
CONECT   63   54                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  136    0
END

View in JSmol

Synonyms

Value	Source
(2S,3S,4R,5R)-2-{[(2S,3S,4R,5S,6S)-3-(acetyloxy)-5-hydroxy-6-{[5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-7-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-3-yl]oxy}-2-methyloxan-4-yl]oxy}-3,5-dihydroxyoxan-4-yl acetic acid	Generator

Chemical Formula

C₄₂H₅₂O₂₁

Average Mass

892.8570 Da

Monoisotopic Mass

892.30011 Da

IUPAC Name

(2S,3S,4R,5S,6S)-4-{[(2S,3S,4R,5R)-4-(acetyloxy)-3,5-dihydroxyoxan-2-yl]oxy}-5-hydroxy-6-{[5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-7-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-3-yl]oxy}-2-methyloxan-3-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C1=C(O[C@@H]2O[C@@H](C)[C@H](OC(C)=O)[C@H](O[C@@H]3OC[C@@H](O)[C@@H](OC(C)=O)[C@@H]3O)[C@@H]2O)C(=O)C2=C(O)C=C(O[C@@H]3O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(CC=C(C)C)=C2O1

InChI Identifier

InChI=1S/C42H52O21/c1-16(2)7-12-22-25(59-41-31(51)30(50)28(48)26(14-43)60-41)13-23(46)27-29(49)38(35(61-36(22)27)20-8-10-21(54-6)11-9-20)63-42-33(53)39(34(17(3)56-42)57-18(4)44)62-40-32(52)37(58-19(5)45)24(47)15-55-40/h7-11,13,17,24,26,28,30-34,37,39-43,46-48,50-53H,12,14-15H2,1-6H3/t17-,24+,26-,28+,30-,31+,32-,33-,34-,37+,39+,40-,41+,42-/m0/s1

InChI Key

NKJJMKATLZNGPP-OSQVXMILSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Epimedium sempervirens	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
Flavonoid-3-o-glycoside
8-prenylated flavone
4p-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
5-hydroxyflavonoid
Phenolic glycoside
O-glycosyl compound
Glycosyl compound
Disaccharide
Chromone
1-benzopyran
Benzopyran
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Oxane
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	1.59	ALOGPS
logP	0.55	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	7.07	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	305.35 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	211.37 m³·mol⁻¹	ChemAxon
Polarizability	88.7 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162894152

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Sempervirenoside A (NP0054009)

MOL for NP0054009 (Sempervirenoside A)

3D MOL for NP0054009 (Sempervirenoside A)

3D SDF for NP0054009 (Sempervirenoside A)

3D-SDF for NP0054009 (Sempervirenoside A)

PDB for NP0054009 (Sempervirenoside A)

3D PDB for NP0054009 (Sempervirenoside A)

SMILES for NP0054009 (Sempervirenoside A)

INCHI for NP0054009 (Sempervirenoside A)

Structure for NP0054009 (Sempervirenoside A)

3D Structure for NP0054009 (Sempervirenoside A)