NP-MRD: Showing NP-Card for (2r,3r)-3-hydroxy-n-[(2r,3s,4s,6r)-3-hydroxy-6-{[8-hydroxy-5-(hydroxymethyl)-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl]oxy}-2-methyloxan-4-yl]-2-methylbutanimidic acid (NP0151654)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 08:00:07 UTC

Updated at

2022-09-02 08:00:07 UTC

NP-MRD ID

NP0151654

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r)-3-hydroxy-n-[(2r,3s,4s,6r)-3-hydroxy-6-{[8-hydroxy-5-(hydroxymethyl)-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl]oxy}-2-methyloxan-4-yl]-2-methylbutanimidic acid

Description

Actinoflavoside 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. Based on a literature review very few articles have been published on Actinoflavoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022210002D          

 37 40  0  0  1  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  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
   -1.4289    0.8250    0.0000 C   0  0  2  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
   -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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    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
    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
    2.8579   -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
    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
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   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
   -3.5724    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   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
   -1.4289    2.4750    0.0000 C   0  0  2  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
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  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  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 11 24  1  0  0  0  0
 24 25  2  0  0  0  0
  4 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  2  0  0  0  0
 29 30  1  4  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  1  0  0  0
 27 36  1  0  0  0  0
  2 36  1  0  0  0  0
 36 37  1  6  0  0  0
M  END

     RDKit          3D

 70 73  0  0  0  0  0  0  0  0999 V2000
   -2.5559   -1.7249   -2.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8064   -1.1394   -1.0776 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2401    0.0617   -1.4979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8102    0.8318   -0.4100 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0849    0.1695    0.4011 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819    0.5419    0.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0261    1.6504    0.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3571    1.9673    0.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9583    3.1988   -0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0379    3.8637   -0.9024 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0697    1.1591    1.3284 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4516    0.0330    1.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1460   -0.2730    1.5230 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5319   -1.4083    2.0416 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2045   -0.7781    2.6863 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6295   -0.8204    2.5769 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0199   -1.2814    1.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3462   -2.3423    0.6118 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6898   -2.7996   -0.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7304   -2.2009   -1.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4049   -1.1658   -0.7436 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0439   -0.7262    0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1116    0.6025    2.7634 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4470    1.4195    1.6973 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0559    2.3416    1.1005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0063    1.3891    0.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2207    0.6008   -0.1375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4262    1.0099    0.4850 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6094    1.0056    0.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6255    1.4710    0.8718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9645    0.5418   -1.3052 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4887    1.6189   -2.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9930   -0.5805   -1.2912 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5813   -1.7241   -0.4062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2539   -0.1173   -0.9475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8713   -0.8502   -0.0098 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1937   -0.9934    1.2233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0081   -2.5982   -2.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5525   -2.1054   -1.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7181   -0.9888   -3.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0687   -1.8675   -0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3376    1.7219   -0.8608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4829    2.3143   -0.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7733    2.8698   -0.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4073    3.8735    0.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4639    4.4270   -0.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0737   -1.9947    2.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0277   -1.5055    3.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5356   -2.7797    1.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1402   -3.6356   -1.1018 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0161   -2.5464   -2.3101 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2120   -0.6945   -1.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6136    0.1094    0.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1926    0.7182    2.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6163    0.9538    3.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2011    2.4413    0.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8749    1.2536    1.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2450    0.8327   -1.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6038    1.0845    1.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0655    0.1113   -1.7942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4160    1.3124   -2.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7480    1.8857   -2.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6566    2.5613   -1.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0419   -0.9462   -2.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9669   -2.4292   -0.9985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5159   -2.2292   -0.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0256   -1.3083    0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2712    0.8722   -0.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7081   -1.5416   -0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6116   -1.7201    1.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
 34 33  1  0
 33 35  1  0
 33 31  1  0
 31 32  1  0
 31 29  1  0
 29 30  1  0
 29 28  2  0
 28 27  1  0
 27 26  1  0
 26  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
 11 24  1  0
 24 25  2  0
 24 23  1  0
 23 16  1  0
 16 15  1  0
 15 12  1  0
 12 13  2  0
 13 14  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  2 36  1  0
 36 37  1  0
 36 27  1  0
 13  6  1  0
 22 17  1  0
 12 11  1  0
 34 65  1  0
 34 66  1  0
 34 67  1  0
 33 64  1  6
 35 68  1  0
 31 60  1  6
 32 61  1  0
 32 62  1  0
 32 63  1  0
 30 59  1  0
 27 58  1  6
 26 56  1  0
 26 57  1  0
  4 42  1  6
  7 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 23 54  1  0
 23 55  1  0
 16 48  1  1
 14 47  1  0
 18 49  1  0
 19 50  1  0
 20 51  1  0
 21 52  1  0
 22 53  1  0
  2 41  1  1
  1 38  1  0
  1 39  1  0
  1 40  1  0
 36 69  1  1
 37 70  1  0
M  END


  Mrv1652309022210002D          

 37 40  0  0  1  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  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
   -1.4289    0.8250    0.0000 C   0  0  2  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
   -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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    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
    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
    2.8579   -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
    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
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   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
   -3.5724    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   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
   -1.4289    2.4750    0.0000 C   0  0  2  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
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  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  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 11 24  1  0  0  0  0
 24 25  2  0  0  0  0
  4 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  2  0  0  0  0
 29 30  1  4  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  1  0  0  0
 27 36  1  0  0  0  0
  2 36  1  0  0  0  0
 36 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0151654

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)[C@@H](C)C(O)=N[C@H]1C[C@@H](OC2=CC(CO)=C3C(=O)CC(OC3=C2O)C2=CC=CC=C2)O[C@H](C)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H33NO9/c1-13(14(2)30)27(34)28-18-10-22(35-15(3)24(18)32)36-21-9-17(12-29)23-19(31)11-20(37-26(23)25(21)33)16-7-5-4-6-8-16/h4-9,13-15,18,20,22,24,29-30,32-33H,10-12H2,1-3H3,(H,28,34)/t13-,14-,15-,18+,20?,22-,24-/m1/s1

> <INCHI_KEY>
IHPAYRWYRVVKSK-OQYUADOUSA-N

> <FORMULA>
C27H33NO9

> <MOLECULAR_WEIGHT>
515.559

> <EXACT_MASS>
515.215531647

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
54.805363053227225

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-3-hydroxy-N-[(2R,3S,4S,6R)-3-hydroxy-6-{[8-hydroxy-5-(hydroxymethyl)-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-2-methyloxan-4-yl]-2-methylbutanimidic acid

> <ALOGPS_LOGP>
1.46

> <JCHEM_LOGP>
2.311698467666667

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.614829850395736

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.687228801793536

> <JCHEM_PKA_STRONGEST_BASIC>
2.366991117050147

> <JCHEM_POLAR_SURFACE_AREA>
158.26999999999998

> <JCHEM_REFRACTIVITY>
132.23269999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-3-hydroxy-N-[(2R,3S,4S,6R)-3-hydroxy-6-{[8-hydroxy-5-(hydroxymethyl)-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl]oxy}-2-methyloxan-4-yl]-2-methylbutanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334  -5.390   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  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      -5.335   4.620   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -5.335   9.240   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   26                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   24                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12    6   14                                                  
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   16   24                                                       
CONECT   24   23   11   25                                                  
CONECT   25   24                                                            
CONECT   26    4   27                                                       
CONECT   27   26   28   36                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   27    2   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₃NO₉

Average Mass

515.5590 Da

Monoisotopic Mass

515.21553 Da

IUPAC Name

(2R,3R)-3-hydroxy-N-[(2R,3S,4S,6R)-3-hydroxy-6-{[8-hydroxy-5-(hydroxymethyl)-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-2-methyloxan-4-yl]-2-methylbutanimidic acid

Traditional Name

(2R,3R)-3-hydroxy-N-[(2R,3S,4S,6R)-3-hydroxy-6-{[8-hydroxy-5-(hydroxymethyl)-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl]oxy}-2-methyloxan-4-yl]-2-methylbutanimidic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](O)[C@@H](C)C(O)=N[C@H]1C[C@@H](OC2=CC(CO)=C3C(=O)CC(OC3=C2O)C2=CC=CC=C2)O[C@H](C)[C@H]1O

InChI Identifier

InChI=1S/C27H33NO9/c1-13(14(2)30)27(34)28-18-10-22(35-15(3)24(18)32)36-21-9-17(12-29)23-19(31)11-20(37-26(23)25(21)33)16-7-5-4-6-8-16/h4-9,13-15,18,20,22,24,29-30,32-33H,10-12H2,1-3H3,(H,28,34)/t13-,14-,15-,18+,20?,22-,24-/m1/s1

InChI Key

IHPAYRWYRVVKSK-OQYUADOUSA-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

Not Available

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
8-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Monocyclic benzene moiety
Fatty amide
Fatty acyl
Benzenoid
Monosaccharide
N-acyl-amine
Oxane
Secondary alcohol
Ketone
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Ether
Acetal
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Aldehyde
Carbonyl group
Organic oxide
Organopnictogen compound
Aromatic alcohol
Primary alcohol
Organic nitrogen compound
Organooxygen compound
Alcohol
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.46	ALOGPS
logP	2.31	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.69	ChemAxon
pKa (Strongest Basic)	2.37	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	158.27 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	132.23 m³·mol⁻¹	ChemAxon
Polarizability	54.81 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

8824872

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10649514

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r)-3-hydroxy-n-[(2r,3s,4s,6r)-3-hydroxy-6-{[8-hydroxy-5-(hydroxymethyl)-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl]oxy}-2-methyloxan-4-yl]-2-methylbutanimidic acid (NP0151654)

MOL for NP0151654 ((2r,3r)-3-hydroxy-n-[(2r,3s,4s,6r)-3-hydroxy-6-{[8-hydroxy-5-(hydroxymethyl)-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl]oxy}-2-methyloxan-4-yl]-2-methylbutanimidic acid)

3D MOL for NP0151654 ((2r,3r)-3-hydroxy-n-[(2r,3s,4s,6r)-3-hydroxy-6-{[8-hydroxy-5-(hydroxymethyl)-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl]oxy}-2-methyloxan-4-yl]-2-methylbutanimidic acid)

3D SDF for NP0151654 ((2r,3r)-3-hydroxy-n-[(2r,3s,4s,6r)-3-hydroxy-6-{[8-hydroxy-5-(hydroxymethyl)-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl]oxy}-2-methyloxan-4-yl]-2-methylbutanimidic acid)

3D-SDF for NP0151654 ((2r,3r)-3-hydroxy-n-[(2r,3s,4s,6r)-3-hydroxy-6-{[8-hydroxy-5-(hydroxymethyl)-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl]oxy}-2-methyloxan-4-yl]-2-methylbutanimidic acid)

PDB for NP0151654 ((2r,3r)-3-hydroxy-n-[(2r,3s,4s,6r)-3-hydroxy-6-{[8-hydroxy-5-(hydroxymethyl)-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl]oxy}-2-methyloxan-4-yl]-2-methylbutanimidic acid)

3D PDB for NP0151654 ((2r,3r)-3-hydroxy-n-[(2r,3s,4s,6r)-3-hydroxy-6-{[8-hydroxy-5-(hydroxymethyl)-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl]oxy}-2-methyloxan-4-yl]-2-methylbutanimidic acid)

SMILES for NP0151654 ((2r,3r)-3-hydroxy-n-[(2r,3s,4s,6r)-3-hydroxy-6-{[8-hydroxy-5-(hydroxymethyl)-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl]oxy}-2-methyloxan-4-yl]-2-methylbutanimidic acid)

INCHI for NP0151654 ((2r,3r)-3-hydroxy-n-[(2r,3s,4s,6r)-3-hydroxy-6-{[8-hydroxy-5-(hydroxymethyl)-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl]oxy}-2-methyloxan-4-yl]-2-methylbutanimidic acid)

Structure for NP0151654 ((2r,3r)-3-hydroxy-n-[(2r,3s,4s,6r)-3-hydroxy-6-{[8-hydroxy-5-(hydroxymethyl)-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl]oxy}-2-methyloxan-4-yl]-2-methylbutanimidic acid)

3D Structure for NP0151654 ((2r,3r)-3-hydroxy-n-[(2r,3s,4s,6r)-3-hydroxy-6-{[8-hydroxy-5-(hydroxymethyl)-4-oxo-2-phenyl-2,3-dihydro-1-benzopyran-7-yl]oxy}-2-methyloxan-4-yl]-2-methylbutanimidic acid)