NP-MRD: Showing NP-Card for (2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one (NP0288711)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 18:31:58 UTC

Updated at

2022-09-09 18:31:58 UTC

NP-MRD ID

NP0288711

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Pinocembrin 7-O-alpha-arabinopyranosyl-(2-1)-beta-glucopyranoside 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. (2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one is found in Centaurea pseudoscabiosa. Based on a literature review very few articles have been published on Pinocembrin 7-O-alpha-arabinopyranosyl-(2-1)-beta-glucopyranoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092220312D          

 39 43  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 O   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
    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  1  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
   -0.7145   -0.4125    0.0000 C   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
   -1.4289    0.8250    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    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
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  1  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  2  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
    5.0013    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  2  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
    6.4302   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  1  0  0  0
 27 26  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 27 34  1  0  0  0  0
 34 35  1  6  0  0  0
 14 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 12 39  1  0  0  0  0
  2 39  1  0  0  0  0
M  END

     RDKit          3D

 69 73  0  0  0  0  0  0  0  0999 V2000
    4.4882   -3.8552    1.3823 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2278   -2.6632    1.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1776   -1.5348    1.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4788   -0.8430    2.8663 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3520    0.0298    3.6113 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8822    0.7329    4.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6947    1.5610    5.4395 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0134    1.7529    5.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4924    1.0548    4.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6749    0.2200    3.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2951   -0.2575    2.3635 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4834   -0.9650    1.4654 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2601   -0.4475    1.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4271   -1.1436    0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7325   -0.5821   -0.1907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8526   -0.9506   -0.8983 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3754   -2.0131   -1.7577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4047   -2.5841   -2.4337 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9420   -3.8502   -3.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8656   -3.5651   -3.9631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0341   -1.6641   -3.4447 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3593   -2.0483   -3.6563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8841   -0.2219   -3.1298 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1293    0.3669   -4.1861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3452    0.1404   -1.7786 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0495    1.1729   -1.1991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4655    2.3685   -1.0396 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6094    2.8528    0.2464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8906    2.6794    0.7433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9470    3.1598   -0.2230 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4784    2.0488   -0.8654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3363    4.0460   -1.2566 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2966    4.4078   -2.2256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2223    3.3468   -1.9491 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3259    4.2672   -2.5187 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8779   -2.3397   -0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1163   -2.9241    0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4976   -4.1330   -0.4078 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8956   -2.1954    0.9692 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2020   -0.8552    0.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1631   -1.9180    1.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2408   -1.7266    3.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8459    0.5869    4.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3178    2.1110    6.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6303    2.4244    5.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5320    1.1992    3.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1781   -0.2674    2.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9312    0.5274    1.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6105   -1.5407   -0.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2275   -2.8965   -1.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7503   -4.2090   -3.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7339   -4.6573   -2.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2000   -4.2534   -3.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5225   -1.8684   -4.4360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9095   -1.6904   -2.9323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9015    0.2539   -3.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8977   -0.3046   -4.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3557    0.7017   -2.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4090    2.4400   -1.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0191    1.6476    1.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9776    3.3074    1.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7724    3.6533    0.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0630    1.5395   -0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9922    5.0109   -0.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5682    5.3527   -2.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6174    2.7507   -2.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9240    4.8544   -3.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3212   -2.9410   -0.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3008   -4.6600   -0.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 36  2  0
 36 37  1  0
 37 38  1  0
 37 39  2  0
 39  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4 11  1  0
 11 12  1  0
 12 13  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 16 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 25 23  1  0
 23 24  1  0
 23 21  1  0
 21 22  1  0
 21 18  1  0
 13 14  1  0
 10  5  1  0
 34 27  1  0
 12 39  1  0
 20 53  1  0
 19 51  1  0
 19 52  1  0
 18 50  1  1
 16 49  1  1
 36 68  1  0
 38 69  1  0
  3 40  1  0
  3 41  1  0
  4 42  1  1
 13 48  1  0
  6 43  1  0
  7 44  1  0
  8 45  1  0
  9 46  1  0
 10 47  1  0
 25 58  1  6
 27 59  1  6
 29 60  1  0
 29 61  1  0
 30 62  1  1
 31 63  1  0
 32 64  1  1
 33 65  1  0
 34 66  1  6
 35 67  1  0
 23 56  1  1
 24 57  1  0
 21 54  1  6
 22 55  1  0
M  END


  Mrv1652309092220312D          

 39 43  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 O   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
    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  1  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
   -0.7145   -0.4125    0.0000 C   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
   -1.4289    0.8250    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    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
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  1  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  2  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
    5.0013    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  2  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
    6.4302   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  1  0  0  0
 27 26  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 27 34  1  0  0  0  0
 34 35  1  6  0  0  0
 14 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 12 39  1  0  0  0  0
  2 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0288711

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O13/c27-9-18-21(32)22(33)24(39-25-23(34)20(31)15(30)10-35-25)26(38-18)36-12-6-13(28)19-14(29)8-16(37-17(19)7-12)11-4-2-1-3-5-11/h1-7,15-16,18,20-28,30-34H,8-10H2/t15-,16-,18+,20-,21+,22-,23+,24+,25-,26+/m0/s1

> <INCHI_KEY>
MWXORMKINOZEQF-HMLNJVQESA-N

> <FORMULA>
C26H30O13

> <MOLECULAR_WEIGHT>
550.513

> <EXACT_MASS>
550.168641026

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
54.448034115192094

> <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,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

> <JCHEM_LOGP>
-0.2698954249999993

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.115898459291659

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.638899973322069

> <JCHEM_PKA_STRONGEST_BASIC>
-2.98109256933943

> <JCHEM_POLAR_SURFACE_AREA>
204.82999999999998

> <JCHEM_REFRACTIVITY>
127.90410000000003

> <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,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.669   4.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      13.337  -0.000   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   39                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    4   12                                                       
CONECT   12   11   13   39                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   36                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   16   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   27   35                                                  
CONECT   35   34                                                            
CONECT   36   14   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   12    2                                                  
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Value	Source
Pinocembrin 7-O-a-arabinopyranosyl-(2-1)-b-glucopyranoside	Generator
Pinocembrin 7-O-α-arabinopyranosyl-(2-1)-β-glucopyranoside	Generator

Chemical Formula

C₂₆H₃₀O₁₃

Average Mass

550.5130 Da

Monoisotopic Mass

550.16864 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C26H30O13/c27-9-18-21(32)22(33)24(39-25-23(34)20(31)15(30)10-35-25)26(38-18)36-12-6-13(28)19-14(29)8-16(37-17(19)7-12)11-4-2-1-3-5-11/h1-7,15-16,18,20-28,30-34H,8-10H2/t15-,16-,18+,20-,21+,22-,23+,24+,25-,26+/m0/s1

InChI Key

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

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

101211576

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one (NP0288711)

MOL for NP0288711 ((2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0288711 ((2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0288711 ((2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0288711 ((2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0288711 ((2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0288711 ((2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0288711 ((2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0288711 ((2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0288711 ((2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0288711 ((2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)