NP-MRD: Showing NP-Card for Variabiloside A (NP0053946)

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Record Information

Version

2.0

Created at

2022-04-28 00:27:13 UTC

Updated at

2022-04-28 00:27:13 UTC

NP-MRD ID

NP0053946

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Variabiloside A

Description

(2S,3R,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-7-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-3-yl]oxy}-4,5-dihydroxy-2-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate 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. Variabiloside A is found in Strychnos variabilis. Based on a literature review very few articles have been published on (2S,3R,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-7-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-3-yl]oxy}-4,5-dihydroxy-2-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282202272D          

 65 71  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
    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  1  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    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
    2.8579   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    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
    1.4289   -4.1250    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
    0.7145   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   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
    5.0013   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.9000    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   -2.4750    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
    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   -0.4125    0.0000 O   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
    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
  5  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
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 17 19  1  6  0  0  0
 19 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 25 27  1  1  0  0  0
 24 28  1  1  0  0  0
 23 29  1  1  0  0  0
 22 30  1  6  0  0  0
 16 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 36 41  1  0  0  0  0
 39 42  1  0  0  0  0
 15 43  1  6  0  0  0
 14 44  1  6  0  0  0
  8 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
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 45 50  1  0  0  0  0
 49 51  1  0  0  0  0
 48 52  1  0  0  0  0
  3 53  1  0  0  0  0
  1 54  1  0  0  0  0
 55 54  1  1  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 55 60  1  0  0  0  0
 59 61  1  6  0  0  0
 61 62  1  0  0  0  0
 58 63  1  6  0  0  0
 57 64  1  1  0  0  0
 56 65  1  6  0  0  0
M  END

     RDKit          3D

111117  0  0  0  0  0  0  0  0999 V2000
   -5.2682   -5.1576   -1.6138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1101   -4.2733   -1.9426 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7011   -3.6190   -0.7814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6983   -2.7289   -1.1888 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6911   -1.6613   -0.3233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1142   -0.4792   -0.8426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0556    0.5996    0.2115 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7875    0.7684    0.6635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2977   -0.0758    1.6041 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1347    0.4906    2.2176 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1328    0.1462    1.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8908    0.8888    1.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4634    2.1383    0.4267 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4252    2.9071    0.8540 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0492    4.0974    0.2114 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7328    4.5374   -0.8952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3678    5.7310   -1.5509 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890    3.7782   -1.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4917    4.2105   -2.4690 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1385    2.6124   -0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1215    0.4761    0.6575 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6432   -0.6168    1.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9259   -0.9271    0.6620 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5579   -2.0705    1.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8370   -2.4451    0.6861 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6847   -1.7313   -0.1573 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0180   -2.4352   -1.3222 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7520   -1.6770   -2.1986 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8453   -1.0826   -3.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8604   -0.2694   -2.7286 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5041   -0.5276   -1.5943 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6990    0.6381   -1.6036 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0190   -0.8559   -0.2373 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1682   -1.6408   -0.3934 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9834   -1.5249    0.5907 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6911   -0.8314    1.7864 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8614   -2.8807    1.9388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5596   -2.5884    2.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9488   -3.4492    3.2454 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9578   -1.4331    1.9563 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6907   -1.0512    2.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9999   -1.7242    3.1046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458   -0.4018    2.7146 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7459   -1.6775    2.7218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3965    0.5791    2.6312 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3382    0.2175    3.5894 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1119    0.4364    1.2812 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0817    1.4259    1.2485 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4354    1.2968    1.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8938    0.1194    1.2018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3365    2.4765    1.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7881    3.6639    1.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5442    4.8786    1.1225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8606    6.0771    1.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5558    7.2597    1.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9335    7.3183    1.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6285    8.5423    0.9688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5873    6.1128    1.0063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9141    4.9045    1.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4013   -3.3925   -1.4451 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7437   -2.7221   -2.4852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6731   -4.8407   -1.8383 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5907   -5.6990   -0.7671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9656   -5.0122   -2.5837 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2901   -6.3811   -2.5555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9338   -6.0015   -0.9511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7001   -5.5572   -2.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0405   -4.5827   -1.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4469   -3.4984   -2.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0688   -2.3115   -2.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5283   -0.1837   -1.7371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1792   -0.5435   -1.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3222    1.5962   -0.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9216   -1.0367    1.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1390    2.6188    1.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7857    4.6372    0.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8661    6.0493   -2.3565 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2631    3.6464   -2.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9653    2.0291   -1.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4314   -0.2644   -0.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2879   -0.7667   -0.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4929   -2.3023   -2.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4294   -0.4640   -3.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3479   -1.8638   -3.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6044    0.3915   -3.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3411   -0.3034   -2.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8186    1.1000   -0.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
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 65111  1  0
M  END


  Mrv1652304282202272D          

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M  END
> <DATABASE_ID>
NP0053946

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1O[C@@H](OC[C@@H]2O[C@@H](OC3=C(OC4=CC(O[C@@H]5O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]5O)=CC(O)=C4C3=O)C3=CC=C(O)C(O)=C3)[C@H](O)[C@H](O)[C@H]2OC(=O)\C=C\C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C42H46O23/c1-15-28(49)31(52)34(55)40(59-15)58-14-25-38(64-26(48)9-4-16-2-6-18(44)7-3-16)33(54)36(57)42(63-25)65-39-30(51)27-22(47)11-19(60-41-35(56)32(53)29(50)24(13-43)62-41)12-23(27)61-37(39)17-5-8-20(45)21(46)10-17/h2-12,15,24-25,28-29,31-36,38,40-47,49-50,52-57H,13-14H2,1H3/b9-4+/t15-,24+,25+,28+,29-,31+,32+,33+,34-,35-,36-,38+,40-,41-,42+/m1/s1

> <INCHI_KEY>
MTAIYYRXJVZTFX-CONJALEFSA-N

> <FORMULA>
C42H46O23

> <MOLECULAR_WEIGHT>
918.807

> <EXACT_MASS>
918.242987741

> <JCHEM_ACCEPTOR_COUNT>
22

> <JCHEM_ATOM_COUNT>
111

> <JCHEM_AVERAGE_POLARIZABILITY>
87.68945846926593

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-7-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-3-yl]oxy}-4,5-dihydroxy-2-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
-0.40650367200000037

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.512189189438836

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.081697180565891

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6940091170780818

> <JCHEM_POLAR_SURFACE_AREA>
370.9700000000001

> <JCHEM_REFRACTIVITY>
213.83810000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-7-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-3-yl]oxy}-4,5-dihydroxy-2-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <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  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -0.000 -13.860   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.336 -16.170   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.002 -16.940   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       8.002 -18.480   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    6   54                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   53                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   45                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   44                                                  
CONECT   15   14   16   43                                                  
CONECT   16   15   17   31                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   30                                                  
CONECT   23   22   24   29                                                  
CONECT   24   23   25   28                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   21                                                       
CONECT   27   25                                                            
CONECT   28   24                                                            
CONECT   29   23                                                            
CONECT   30   22                                                            
CONECT   31   16   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   42                                                  
CONECT   40   39   41                                                       
CONECT   41   40   36                                                       
CONECT   42   39                                                            
CONECT   43   15                                                            
CONECT   44   14                                                            
CONECT   45    8   46   50                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   52                                                  
CONECT   49   48   50   51                                                  
CONECT   50   49   45                                                       
CONECT   51   49                                                            
CONECT   52   48                                                            
CONECT   53    3                                                            
CONECT   54    1   55                                                       
CONECT   55   54   56   60                                                  
CONECT   56   55   57   65                                                  
CONECT   57   56   58   64                                                  
CONECT   58   57   59   63                                                  
CONECT   59   58   60   61                                                  
CONECT   60   59   55                                                       
CONECT   61   59   62                                                       
CONECT   62   61                                                            
CONECT   63   58                                                            
CONECT   64   57                                                            
CONECT   65   56                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  142    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-7-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-3-yl]oxy}-4,5-dihydroxy-2-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₄₂H₄₆O₂₃

Average Mass

918.8070 Da

Monoisotopic Mass

918.24299 Da

IUPAC Name

Traditional Name

(2S,3R,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-7-{[(2S,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-3-yl]oxy}-4,5-dihydroxy-2-({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

C[C@H]1O[C@@H](OC[C@@H]2O[C@@H](OC3=C(OC4=CC(O[C@@H]5O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]5O)=CC(O)=C4C3=O)C3=CC=C(O)C(O)=C3)[C@H](O)[C@H](O)[C@H]2OC(=O)\C=C\C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C42H46O23/c1-15-28(49)31(52)34(55)40(59-15)58-14-25-38(64-26(48)9-4-16-2-6-18(44)7-3-16)33(54)36(57)42(63-25)65-39-30(51)27-22(47)11-19(60-41-35(56)32(53)29(50)24(13-43)62-41)12-23(27)61-37(39)17-5-8-20(45)21(46)10-17/h2-12,15,24-25,28-29,31-36,38,40-47,49-50,52-57H,13-14H2,1H3/b9-4+/t15-,24+,25+,28+,29-,31+,32+,33+,34-,35-,36-,38+,40-,41-,42+/m1/s1

InChI Key

MTAIYYRXJVZTFX-CONJALEFSA-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
Strychnos variabilis	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
Hydroxyflavonoid
Flavone
5-hydroxyflavonoid
4'-hydroxyflavonoid
3'-hydroxyflavonoid
Phenolic glycoside
Coumaric acid ester
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid or derivatives
O-glycosyl compound
Glycosyl compound
Disaccharide
Chromone
1-benzopyran
Benzopyran
Styrene
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Fatty acid ester
Fatty acyl
Benzenoid
Pyran
Oxane
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
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	1.1	ALOGPS
logP	-0.41	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.08	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	22	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	370.97 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	213.84 m³·mol⁻¹	ChemAxon
Polarizability	87.69 Å³	ChemAxon
Number of Rings	7	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

162978661

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Variabiloside A (NP0053946)

MOL for NP0053946 (Variabiloside A)

3D MOL for NP0053946 (Variabiloside A)

3D SDF for NP0053946 (Variabiloside A)

3D-SDF for NP0053946 (Variabiloside A)

PDB for NP0053946 (Variabiloside A)

3D PDB for NP0053946 (Variabiloside A)

SMILES for NP0053946 (Variabiloside A)

INCHI for NP0053946 (Variabiloside A)

Structure for NP0053946 (Variabiloside A)

3D Structure for NP0053946 (Variabiloside A)