NP-MRD: Showing NP-Card for Larycitrin 3-(4''-malonylrhamnoside) (NP0060281)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 05:21:50 UTC

Updated at

2022-04-28 05:21:50 UTC

NP-MRD ID

NP0060281

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Larycitrin 3-(4''-malonylrhamnoside)

Description

3-{[(2S,3R,4S,5S,6S)-6-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl]oxy}-3-oxopropanoic acid belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Larycitrin 3-(4''-malonylrhamnoside) is found in Ribes alpinum . Based on a literature review very few articles have been published on 3-{[(2S,3R,4S,5S,6S)-6-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl]oxy}-3-oxopropanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207212D          

 40 43  0  0  1  0            999 V2000
   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    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
   -3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 O   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 O   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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  1  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
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  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
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    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
   -2.8579    0.8250    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
    2.1434   -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
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
  5  9  1  0  0  0  0
  4 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 11 17  2  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  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
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  6  0  0  0
 22 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 21 33  1  6  0  0  0
 20 34  1  1  0  0  0
 14 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
 13 38  2  0  0  0  0
 37 39  1  0  0  0  0
 35 40  1  0  0  0  0
M  END

     RDKit          3D

 64 67  0  0  0  0  0  0  0  0999 V2000
   -4.1964   -4.7770   -0.4735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4084   -4.7076   -1.6490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7891   -3.5057   -1.9573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9236   -2.3898   -1.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3073   -1.1866   -1.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4901   -0.1026   -0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4585   -0.2211    0.4207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7107    0.6803    1.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7530    0.4585    2.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0507    1.3833    3.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0982    1.1563    4.1082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3417    2.5504    3.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2781    2.8306    2.3991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6083    4.0072    2.5462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0078    1.8810    1.4480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9994    2.0458    0.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3078    3.0730    0.5505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7675    1.0402   -0.4170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7084    1.3108   -1.2840 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6295    1.0053   -0.9134 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2010    2.2089   -0.4058 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4084    1.9919    0.2098 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2762    2.0903    1.7246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0596    0.7067   -0.2280 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4151    0.6432    0.1846 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9306   -0.3489    0.9993 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1429   -1.2462    1.3906 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3695   -0.3850    1.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1087    0.7868    0.9282 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5044    1.6469    0.2489 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4535    0.8982    1.2351 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9448    0.6494   -1.7446 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7269   -0.3342   -2.2897 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4575    0.4927   -2.0418 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1292    1.2806   -3.1691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5622   -1.1570   -2.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4096   -2.2717   -3.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6352   -2.1964   -4.5740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0347   -3.4446   -3.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8791   -4.5574   -3.9236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6854   -5.7623   -0.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0220   -4.0106   -0.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5547   -4.5089    0.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5432   -2.5114   -0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3098   -0.4654    2.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8264    0.6810    4.9588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5863    3.2645    4.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8754    4.3739    2.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5597    0.2677   -0.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1478    2.8033   -0.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5787    2.9491    1.8970 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8832    1.1759    2.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2431    2.3935    2.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5263   -0.1321    0.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4772   -0.5615    2.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8400   -1.2863    0.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9694    1.6420    0.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2493    1.6324   -2.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5472   -0.4284   -3.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2106   -0.5355   -2.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7448    2.0273   -3.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0885   -0.2508   -2.8868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1932   -1.3106   -4.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3247   -5.4335   -3.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 39  2  0
 39 40  1  0
 39 37  1  0
 37 38  1  0
 37 36  2  0
 36  5  1  0
  5  4  2  0
  5  6  1  0
  6 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 31  1  0
 29 30  2  0
 24 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 18 16  1  0
 16 17  2  0
 16 15  1  0
 15 13  2  0
 13 14  1  0
 13 12  1  0
 12 10  2  0
 10 11  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  4  3  1  0
  7  6  1  0
 34 20  1  0
  8 15  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
 40 64  1  0
 38 63  1  0
 36 62  1  0
  4 44  1  0
 20 49  1  1
 22 50  1  6
 23 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  1
 28 55  1  0
 28 56  1  0
 31 57  1  0
 32 58  1  6
 33 59  1  0
 34 60  1  6
 35 61  1  0
 14 48  1  0
 12 47  1  0
 11 46  1  0
  9 45  1  0
M  END


  Mrv1652304282207212D          

 40 43  0  0  1  0            999 V2000
   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    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
   -3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 O   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 O   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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  1  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
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  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
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    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
   -2.8579    0.8250    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
    2.1434   -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
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
  5  9  1  0  0  0  0
  4 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 11 17  2  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  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
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  6  0  0  0
 22 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 21 33  1  6  0  0  0
 20 34  1  1  0  0  0
 14 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
 13 38  2  0  0  0  0
 37 39  1  0  0  0  0
 35 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0060281

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O15/c1-8-22(39-16(31)7-15(29)30)20(34)21(35)25(37-8)40-24-19(33)17-11(27)5-10(26)6-13(17)38-23(24)9-3-12(28)18(32)14(4-9)36-2/h3-6,8,20-22,25-28,32,34-35H,7H2,1-2H3,(H,29,30)/t8-,20-,21-,22-,25-/m0/s1

> <INCHI_KEY>
CLJHAXXQLXXEAX-TZUKPBLKSA-N

> <FORMULA>
C25H24O15

> <MOLECULAR_WEIGHT>
564.452

> <EXACT_MASS>
564.111520073

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
52.000159183823605

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(2S,3R,4S,5S,6S)-6-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl]oxy}-3-oxopropanoic acid

> <ALOGPS_LOGP>
2.03

> <JCHEM_LOGP>
1.0777572613333333

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.374795766110047

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.626070428330607

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6916265174757363

> <JCHEM_POLAR_SURFACE_AREA>
238.96999999999997

> <JCHEM_REFRACTIVITY>
129.6906

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2S,3R,4S,5S,6S)-6-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl]oxy}-3-oxopropanoic acid

> <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      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.000  10.780   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       1.334   8.470   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+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       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5                                                            
CONECT   10    4                                                            
CONECT   11    2   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   38                                                  
CONECT   14   13   15   35                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   11   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   34                                                  
CONECT   21   20   22   33                                                  
CONECT   22   21   23   26                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   19                                                       
CONECT   25   23                                                            
CONECT   26   22   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   21                                                            
CONECT   34   20                                                            
CONECT   35   14   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37   13                                                       
CONECT   39   37                                                            
CONECT   40   35                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Value	Source
3-{[(2S,3R,4S,5S,6S)-6-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl]oxy}-3-oxopropanoate	Generator

Chemical Formula

C₂₅H₂₄O₁₅

Average Mass

564.4520 Da

Monoisotopic Mass

564.11152 Da

IUPAC Name

3-{[(2S,3R,4S,5S,6S)-6-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl]oxy}-3-oxopropanoic acid

Traditional Name

3-{[(2S,3R,4S,5S,6S)-6-{[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl]oxy}-3-oxopropanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C25H24O15/c1-8-22(39-16(31)7-15(29)30)20(34)21(35)25(37-8)40-24-19(33)17-11(27)5-10(26)6-13(17)38-23(24)9-3-12(28)18(32)14(4-9)36-2/h3-6,8,20-22,25-28,32,34-35H,7H2,1-2H3,(H,29,30)/t8-,20-,21-,22-,25-/m0/s1

InChI Key

CLJHAXXQLXXEAX-TZUKPBLKSA-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
Ribes alpinum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3'-hydroxyflavonoid
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Chromone
1-benzopyran
Methoxyphenol
Benzopyran
Phenoxy compound
Methoxybenzene
Phenol ether
Catechol
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Sugar acid
Pyranone
Phenol
Alkyl aryl ether
Benzenoid
1,3-dicarbonyl compound
Pyran
Oxane
Monosaccharide
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
1,2-diol
Oxacycle
Organoheterocyclic compound
Ether
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	2.03	ALOGPS
logP	1.08	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.63	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	238.97 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	129.69 m³·mol⁻¹	ChemAxon
Polarizability	52 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

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

163103682

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Larycitrin 3-(4''-malonylrhamnoside) (NP0060281)

MOL for NP0060281 (Larycitrin 3-(4''-malonylrhamnoside))

3D MOL for NP0060281 (Larycitrin 3-(4''-malonylrhamnoside))

3D SDF for NP0060281 (Larycitrin 3-(4''-malonylrhamnoside))

3D-SDF for NP0060281 (Larycitrin 3-(4''-malonylrhamnoside))

PDB for NP0060281 (Larycitrin 3-(4''-malonylrhamnoside))

3D PDB for NP0060281 (Larycitrin 3-(4''-malonylrhamnoside))

SMILES for NP0060281 (Larycitrin 3-(4''-malonylrhamnoside))

INCHI for NP0060281 (Larycitrin 3-(4''-malonylrhamnoside))

Structure for NP0060281 (Larycitrin 3-(4''-malonylrhamnoside))

3D Structure for NP0060281 (Larycitrin 3-(4''-malonylrhamnoside))