NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-6-{[(2s,3r,4s,5s,6r)-2-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (NP0328466)

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Record Information

Version

2.0

Created at

2022-09-12 11:57:39 UTC

Updated at

2022-09-12 11:57:39 UTC

NP-MRD ID

NP0328466

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6s)-6-{[(2s,3r,4s,5s,6r)-2-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Description

Isoscoparin 2''-O-[6-(E)-feruloylglucoside], also known as 2''-(6-feruloylglucosyl)isoscoparin, belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Thus, isoscoparin 2''-O-[6-(e)-feruloylglucoside] is considered to be a flavonoid. Isoscoparin 2''-O-[6-(E)-feruloylglucoside] is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. [(2r,3s,4s,5r,6s)-6-{[(2s,3r,4s,5s,6r)-2-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate is found in Cucumis sativus. Based on a literature review very few articles have been published on isoscoparin 2''-O-[6-(E)-feruloylglucoside].

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309122213572D          

 57 62  0  0  1  0            999 V2000
   -8.5737    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -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
   -4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  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 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   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
    2.8579    0.0000    0.0000 O   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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   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
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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
    2.8579   -1.6500    0.0000 C   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
    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
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  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
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 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
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  2  0  0  0  0
 25 33  1  0  0  0  0
 24 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 22 37  1  0  0  0  0
 37 38  2  0  0  0  0
 18 38  1  0  0  0  0
 38 39  1  0  0  0  0
 17 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  6  0  0  0
 42 43  1  0  0  0  0
 41 44  1  0  0  0  0
 44 45  1  1  0  0  0
 44 46  1  0  0  0  0
 16 46  1  0  0  0  0
 46 47  1  6  0  0  0
 14 48  1  0  0  0  0
 48 49  1  1  0  0  0
 48 50  1  0  0  0  0
 50 51  1  6  0  0  0
 50 52  1  0  0  0  0
 12 52  1  0  0  0  0
 52 53  1  1  0  0  0
  5 54  2  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
  3 56  1  0  0  0  0
 56 57  1  0  0  0  0
M  END

     RDKit          3D

 97102  0  0  0  0  0  0  0  0999 V2000
    6.3019   -1.0259    5.9936 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5278   -1.7078    5.8040 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0245   -1.7685    4.4991 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3613   -1.2001    3.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8564   -1.2612    2.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2151   -0.6657    0.9817 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0842    0.0136    1.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5168    0.5837   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1447    0.3963   -1.3157 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3519    1.3039   -0.2802 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7865    1.8705   -1.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3992    0.8042   -2.4074 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4239    0.0146   -1.8900 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4237   -0.2624   -2.7745 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4896    0.7060   -2.9545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8300    0.3497   -2.5728 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2723    1.3295   -1.5902 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3510    1.0600   -0.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9116    2.1470    0.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3755    3.4264   -0.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9052    1.9605    0.9340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4136    0.7015    1.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3890    0.5435    2.0693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9188   -0.6093    2.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0135   -0.6837    3.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4679    0.4968    3.9218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4992    0.4921    4.8564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0967   -0.6827    5.2446 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1421   -0.6922    6.1900 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.2619   -3.0303    5.0888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8305   -4.2580    4.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6113   -1.8441    3.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4550   -1.7344    1.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4085   -1.6221    0.8368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9756   -2.6405    0.2828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8638   -0.3849    0.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8317   -0.2039   -0.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3359   -1.2979   -1.0005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5322    2.5894   -2.1288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1858    2.7590   -3.4253 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6318    4.1196   -3.9800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    4.2217   -5.3310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5544    1.7441   -4.4248 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7312    1.8022   -5.5484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6796    0.3893   -3.8459 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9974    0.1600   -3.5137 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0163   -0.8530   -4.0336 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9094   -1.8394   -3.6076 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8360    0.2175   -4.7118 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1866    0.6340   -5.8798 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0843    2.1376   -4.2745 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0538   -1.9191    1.9594 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7338   -2.4973    3.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0797   -0.8997    7.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4156   -0.0295    5.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4203   -0.6855    3.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6863   -0.7785    0.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5874    0.1412    1.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4429    2.6475   -1.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8812    2.4351   -1.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2780    0.1116   -2.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8552   -1.1428   -2.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7710   -0.6637   -2.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3684    1.5340   -0.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7684    4.2215    0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3524    2.8102    1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0199    1.4456    3.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8332    1.4153    5.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5436   -1.5846    6.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8721   -4.5122    5.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6861   -4.2310    3.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6082   -5.0362    4.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2863   -2.7672    3.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8229   -2.7226    1.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0574    2.8659   -3.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0873    4.9355   -3.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7022    4.2789   -3.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2212    5.1686   -5.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5789    2.0349   -4.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0794    2.2782   -5.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3647   -0.4470   -4.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4435   -0.3565   -4.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2825   -1.2207   -4.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3809   -2.6842   -3.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8521   -0.1344   -5.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1586    2.0392   -3.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

  Mrv1652309122213572D          

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  6  7  2  0  0  0  0
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  8  9  2  0  0  0  0
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 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
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 35 36  2  0  0  0  0
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 22 37  1  0  0  0  0
 37 38  2  0  0  0  0
 18 38  1  0  0  0  0
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 17 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  6  0  0  0
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 41 44  1  0  0  0  0
 44 45  1  1  0  0  0
 44 46  1  0  0  0  0
 16 46  1  0  0  0  0
 46 47  1  6  0  0  0
 14 48  1  0  0  0  0
 48 49  1  1  0  0  0
 48 50  1  0  0  0  0
 50 51  1  6  0  0  0
 50 52  1  0  0  0  0
 12 52  1  0  0  0  0
 52 53  1  1  0  0  0
  5 54  2  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
  3 56  1  0  0  0  0
 56 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328466

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\C(=O)OC[C@H]2O[C@@H](O[C@@H]3[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]3C3=C(O)C=C4OC(=CC(=O)C4=C3O)C3=CC=C(O)C(OC)=C3)[C@H](O)[C@@H](O)[C@@H]2O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C38H40O19/c1-51-22-9-15(3-6-17(22)40)4-8-27(44)53-14-26-31(46)33(48)35(50)38(56-26)57-37-34(49)30(45)25(13-39)55-36(37)29-20(43)12-24-28(32(29)47)19(42)11-21(54-24)16-5-7-18(41)23(10-16)52-2/h3-12,25-26,30-31,33-41,43,45-50H,13-14H2,1-2H3/b8-4+/t25-,26-,30-,31-,33+,34+,35-,36+,37-,38+/m1/s1

> <INCHI_KEY>
DJZOTDSGEBENPL-LWHZWZDQSA-N

> <FORMULA>
C38H40O19

> <MOLECULAR_WEIGHT>
800.719

> <EXACT_MASS>
800.216379068

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
97

> <JCHEM_AVERAGE_POLARIZABILITY>
79.89132096980748

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
0.5935154480000002

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.737387797673939

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.138218271332747

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6490925210988543

> <JCHEM_POLAR_SURFACE_AREA>
301.05

> <JCHEM_REFRACTIVITY>
192.9205

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-6-{[(2S,3R,4S,5S,6R)-2-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0     -16.004   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0     -14.670   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0     -14.670   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -13.337   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -13.337  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0     -14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0     -16.004  -0.000   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0     -16.004   1.540   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0     -17.338   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   56                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   54                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   52                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   48                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   46                                                  
CONECT   17   16   18   40                                                  
CONECT   18   17   19   38                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   37                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   34                                                  
CONECT   25   24   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   25                                                       
CONECT   34   24   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   22   38                                                  
CONECT   38   37   18   39                                                  
CONECT   39   38                                                            
CONECT   40   17   41                                                       
CONECT   41   40   42   44                                                  
CONECT   42   41   43                                                       
CONECT   43   42                                                            
CONECT   44   41   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   16   47                                                  
CONECT   47   46                                                            
CONECT   48   14   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   12   53                                                  
CONECT   53   52                                                            
CONECT   54    5   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55    3   57                                                  
CONECT   57   56                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  124    0
END

View in JSmol

Synonyms

Value	Source
2''-(6-Feruloylglucosyl)isoscoparin	ChEBI
2''-O-(6-Feruloylglucosyl)isoscoparin	ChEBI
2''-O-[6-(e)-Feruloylglucosyl]isoscoparin	ChEBI
Isoscoparin 2''-[6-(e)-feruloylglucoside]	ChEBI

Chemical Formula

C₃₈H₄₀O₁₉

Average Mass

800.7190 Da

Monoisotopic Mass

800.21638 Da

IUPAC Name

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

Traditional Name

[(2R,3S,4S,5R,6S)-6-{[(2S,3R,4S,5S,6R)-2-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C(=O)OC[C@H]2O[C@@H](O[C@@H]3[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]3C3=C(O)C=C4OC(=CC(=O)C4=C3O)C3=CC=C(O)C(OC)=C3)[C@H](O)[C@@H](O)[C@@H]2O)=CC=C1O

InChI Identifier

InChI=1S/C38H40O19/c1-51-22-9-15(3-6-17(22)40)4-8-27(44)53-14-26-31(46)33(48)35(50)38(56-26)57-37-34(49)30(45)25(13-39)55-36(37)29-20(43)12-24-28(32(29)47)19(42)11-21(54-24)16-5-7-18(41)23(10-16)52-2/h3-12,25-26,30-31,33-41,43,45-50H,13-14H2,1-2H3/b8-4+/t25-,26-,30-,31-,33+,34+,35-,36+,37-,38+/m1/s1

InChI Key

DJZOTDSGEBENPL-LWHZWZDQSA-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
Cucumis sativus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid C-glycosides

Alternative Parents

Substituents

Flavonoid c-glycoside
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
Flavone
Phenolic glycoside
Coumaric acid or derivatives
Cinnamic acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
O-glycosyl compound
Disaccharide
Glycosyl compound
Chromone
C-glycosyl compound
1-benzopyran
Benzopyran
Methoxyphenol
Styrene
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Fatty acid ester
Pyranone
Phenol
Fatty acyl
Pyran
Monocyclic benzene moiety
Oxane
Benzenoid
Heteroaromatic compound
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Alcohol
Primary 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	0.59	ChemAxon
pKa (Strongest Acidic)	6.14	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	301.05 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	192.92 m³·mol⁻¹	ChemAxon
Polarizability	79.89 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

C00006336

Chemspider ID

10306154

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21722000

PDB ID

Not Available

ChEBI ID

131831

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6s)-6-{[(2s,3r,4s,5s,6r)-2-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (NP0328466)

MOL for NP0328466 ([(2r,3s,4s,5r,6s)-6-{[(2s,3r,4s,5s,6r)-2-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D MOL for NP0328466 ([(2r,3s,4s,5r,6s)-6-{[(2s,3r,4s,5s,6r)-2-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D SDF for NP0328466 ([(2r,3s,4s,5r,6s)-6-{[(2s,3r,4s,5s,6r)-2-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D-SDF for NP0328466 ([(2r,3s,4s,5r,6s)-6-{[(2s,3r,4s,5s,6r)-2-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

PDB for NP0328466 ([(2r,3s,4s,5r,6s)-6-{[(2s,3r,4s,5s,6r)-2-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D PDB for NP0328466 ([(2r,3s,4s,5r,6s)-6-{[(2s,3r,4s,5s,6r)-2-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

SMILES for NP0328466 ([(2r,3s,4s,5r,6s)-6-{[(2s,3r,4s,5s,6r)-2-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

INCHI for NP0328466 ([(2r,3s,4s,5r,6s)-6-{[(2s,3r,4s,5s,6r)-2-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

Structure for NP0328466 ([(2r,3s,4s,5r,6s)-6-{[(2s,3r,4s,5s,6r)-2-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D Structure for NP0328466 ([(2r,3s,4s,5r,6s)-6-{[(2s,3r,4s,5s,6r)-2-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)