NP-MRD: Showing NP-Card for (2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one (NP0243535)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 04:06:16 UTC

Updated at

2022-09-07 04:06:16 UTC

NP-MRD ID

NP0243535

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

Description

Pinocembrin 7-rhamnosylglucoside, also known as pinocembrin 7-O-neohesperidoside, 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. Thus, pinocembrin 7-rhamnosylglucoside is considered to be a flavonoid. Pinocembrin 7-rhamnosylglucoside 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. (2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one is found in Litchi chinensis, Nierembergia linariifolia, Onychium japonicum and Sparattosperma leucanthum. (2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one was first documented in 2011 (PMID: 21287989). Based on a literature review very few articles have been published on pinocembrin 7-rhamnosylglucoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072206062D          

 40 44  0  0  1  0            999 V2000
   -5.7158    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  2  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  1  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
   -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 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 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
    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  2  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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    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
   -3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  2  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    2.0625    0.0000 C   0  0  2  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
   -4.2868    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    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
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 15  1  0  0  0  0
 14 16  1  0  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
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 13 25  1  0  0  0  0
 25 26  2  0  0  0  0
  7 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
  6 33  1  0  0  0  0
 33 34  1  6  0  0  0
  4 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
  2 39  1  0  0  0  0
 39 40  1  6  0  0  0
M  END

     RDKit          3D

 72 76  0  0  0  0  0  0  0  0999 V2000
   -2.7498    3.6274    1.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0157    2.1132    1.6982 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4024    1.5438    0.6619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0546    0.8016   -0.2373 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9752   -0.5622   -0.0886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4635   -1.2436   -1.1713 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1559   -1.9171   -0.9166 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0504   -1.1181   -1.1125 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9491   -0.8957   -0.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9499   -1.4454    1.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9928   -1.1751    1.9716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9435   -1.7547    3.2021 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0114   -0.3441    1.5710 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0537    0.2425    0.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0066   -0.0600   -0.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0908    1.0819   -0.0920 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9977    1.5418    0.8588 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1727    2.2155    0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5944    3.3984    0.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6806    4.0882    0.3563 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3733    3.5825   -0.7152 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9749    2.3866   -1.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8768    1.7179   -0.7955 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3929    0.3919    1.7675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1166   -0.0084    2.4525 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9805   -0.0586    3.6768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0405   -2.9650   -1.8733 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8353   -4.0469   -1.4681 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9081   -5.0031   -2.6325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6998   -6.0807   -2.2246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2524   -3.5560   -1.1998 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3786   -3.4097    0.1780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4342   -2.1745   -1.8153 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0920   -2.2771   -3.1620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5467    1.1401   -0.3696 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7349    2.4359   -0.8007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1216    0.9102    1.0118 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4874    1.1309    1.0615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4542    1.9186    1.9131 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7543    1.5198    3.2382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5538    4.1879    2.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7099    3.8857    0.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7750    3.8734    2.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4817    1.8002    2.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6509    1.0387   -1.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2377   -0.4424   -1.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2429   -2.4233    0.0655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1373   -2.1114    1.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5885   -1.6775    3.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0101    0.3838   -1.5237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4466    2.2575    1.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0768    3.8437    1.6908 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0001    5.0303    0.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2355    4.1354   -1.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5465    2.0223   -2.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5522    0.7854   -1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7565   -0.4908    1.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0846    0.7106    2.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4025   -4.5786   -0.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9049   -5.3309   -2.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4734   -4.5085   -3.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5039   -6.2292   -1.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0231   -4.2681   -1.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0892   -4.2419    0.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4972   -1.9008   -1.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8996   -2.1241   -3.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9961    0.3829   -1.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0101    2.7845   -1.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8649   -0.1171    1.3308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9047    1.1964    0.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0397    2.8748    1.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7242    1.5583    3.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6 33  1  0
 33 34  1  0
 33 31  1  0
 31 32  1  0
 31 28  1  0
 28 29  1  0
 29 30  1  0
 28 27  1  0
 27  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 25  1  0
 25 26  2  0
 25 24  1  0
 24 17  1  0
 17 16  1  0
 16 14  1  0
 14 15  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
  4 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 39  2  1  0
  7  6  1  0
 15  9  1  0
 23 18  1  0
 14 13  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  2 44  1  1
  4 45  1  6
  6 46  1  6
 33 65  1  6
 34 66  1  0
 31 63  1  6
 32 64  1  0
 28 59  1  1
 29 60  1  0
 29 61  1  0
 30 62  1  0
  7 47  1  1
 10 48  1  0
 12 49  1  0
 24 57  1  0
 24 58  1  0
 17 51  1  1
 15 50  1  0
 19 52  1  0
 20 53  1  0
 21 54  1  0
 22 55  1  0
 23 56  1  0
 35 67  1  6
 36 68  1  0
 37 69  1  1
 38 70  1  0
 39 71  1  6
 40 72  1  0
M  END


  Mrv1652309072206062D          

 40 44  0  0  1  0            999 V2000
   -5.7158    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  2  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  1  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
   -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 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 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
    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  2  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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    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
   -3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  2  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    2.0625    0.0000 C   0  0  2  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
   -4.2868    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    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
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 15  1  0  0  0  0
 14 16  1  0  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
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 13 25  1  0  0  0  0
 25 26  2  0  0  0  0
  7 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
  6 33  1  0  0  0  0
 33 34  1  6  0  0  0
  4 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
  2 39  1  0  0  0  0
 39 40  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0243535

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC(O)=C3C(=O)C[C@H](OC3=C2)C2=CC=CC=C2)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O13/c1-11-20(31)22(33)24(35)26(36-11)40-25-23(34)21(32)18(10-28)39-27(25)37-13-7-14(29)19-15(30)9-16(38-17(19)8-13)12-5-3-2-4-6-12/h2-8,11,16,18,20-29,31-35H,9-10H2,1H3/t11-,16-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1

> <INCHI_KEY>
UVPBNPUZWAOBQX-AFUJZTQMSA-N

> <FORMULA>
C27H32O13

> <MOLECULAR_WEIGHT>
564.54

> <EXACT_MASS>
564.18429109

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
55.05973563220199

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

> <JCHEM_LOGP>
0.14667959966666677

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.099568602589088

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.638894422347944

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092569339441

> <JCHEM_POLAR_SURFACE_AREA>
204.82999999999998

> <JCHEM_REFRACTIVITY>
132.32290000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000  -4.620   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       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -8.002   0.000   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -6.668   3.850   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      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -8.002   6.160   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0     -10.669   4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   39                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   35                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   33                                                  
CONECT    7    6    8   27                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   25                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14    9                                                       
CONECT   16   14   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   17   25                                                       
CONECT   25   24   13   26                                                  
CONECT   26   25                                                            
CONECT   27    7   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    6   34                                                  
CONECT   34   33                                                            
CONECT   35    4   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37    2   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Value	Source
Pinocembrin 7-O-neohesperidoside	ChEBI

Chemical Formula

C₂₇H₃₂O₁₃

Average Mass

564.5400 Da

Monoisotopic Mass

564.18429 Da

IUPAC Name

(2S)-7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2S)-7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC(O)=C3C(=O)C[C@H](OC3=C2)C2=CC=CC=C2)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C27H32O13/c1-11-20(31)22(33)24(35)26(36-11)40-25-23(34)21(32)18(10-28)39-27(25)37-13-7-14(29)19-15(30)9-16(38-17(19)8-13)12-5-3-2-4-6-12/h2-8,11,16,18,20-29,31-35H,9-10H2,1H3/t11-,16-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1

InChI Key

UVPBNPUZWAOBQX-AFUJZTQMSA-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
Litchi chinensis	LOTUS Database	35616633
Nierembergia linariifolia	LOTUS Database	35616633
Onychium japonicum	LOTUS Database	35616633
Sparattosperma leucanthum	LOTUS Database	35616633

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
Hydroxyflavonoid
5-hydroxyflavonoid
Flavanone
Flavan
Phenolic glycoside
O-glycosyl compound
Glycosyl compound
Disaccharide
Chromone
Chromane
1-benzopyran
Benzopyran
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Oxane
Vinylogous acid
Secondary alcohol
Ketone
Polyol
Acetal
Ether
Organoheterocyclic compound
Oxacycle
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

disaccharide derivative (CHEBI:8222 )
monohydroxyflavanone (CHEBI:8222 )
flavanone glycoside (CHEBI:8222 )
neohesperidoside (CHEBI:8222 )
flavanones (C09828 )

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	0.15	ChemAxon
pKa (Strongest Acidic)	8.64	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	204.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	132.32 m³·mol⁻¹	ChemAxon
Polarizability	55.06 Å³	ChemAxon
Number of Rings	5	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

C00000993

Chemspider ID

390892

KEGG Compound ID

C09828

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442454

PDB ID

Not Available

ChEBI ID

8222

Good Scents ID

Not Available

References

General References

Xu X, Xie H, Hao J, Jiang Y, Wei X: Flavonoid Glycosides from the Seeds of Litchi chinensis. J Agric Food Chem. 2011 Feb 23;59(4):1205-9. doi: 10.1021/jf104387y. Epub 2011 Feb 2. [PubMed:21287989 ]
LOTUS database [Link]

Showing NP-Card for (2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one (NP0243535)

MOL for NP0243535 ((2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0243535 ((2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0243535 ((2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0243535 ((2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0243535 ((2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0243535 ((2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0243535 ((2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0243535 ((2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0243535 ((2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0243535 ((2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)