NP-MRD: Showing NP-Card for (2r,3r,4s)-2-(4-hydroxyphenyl)-4-{[(2r,3r,4s)-4,7,8-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-3,4-dihydro-2h-1-benzopyran-3,7,8-triol (NP0325129)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-12 05:39:05 UTC

Updated at

2022-09-12 05:39:06 UTC

NP-MRD ID

NP0325129

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4s)-2-(4-hydroxyphenyl)-4-{[(2r,3r,4s)-4,7,8-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-3,4-dihydro-2h-1-benzopyran-3,7,8-triol

Description

(2R,3R,4S)-2-(4-hydroxyphenyl)-3-{[(2R,3R,4S)-3,7,8-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4,7,8-triol belongs to the class of organic compounds known as leucoanthocyanidins. These are flavonoids consisting of a flavan (3,4-dihydro-2-phenyl-2H-1-benzopyran) moiety that carries two hydroxy groups at the C3- and C4-positions. (2r,3r,4s)-2-(4-hydroxyphenyl)-4-{[(2r,3r,4s)-4,7,8-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-3,4-dihydro-2h-1-benzopyran-3,7,8-triol is found in Senegalia caffra. Based on a literature review very few articles have been published on (2R,3R,4S)-2-(4-hydroxyphenyl)-3-{[(2R,3R,4S)-3,7,8-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4,7,8-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122207392D          

 41 46  0  0  1  0            999 V2000
    3.5724    3.7125    0.0000 O   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
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    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
   -1.4289    0.8250    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
   -2.1434    2.0625    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
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    3.5724   -1.2375    0.0000 C   0  0  0  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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 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    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5350    1.3237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  1  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 18 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 31 37  1  0  0  0  0
 16 38  1  0  0  0  0
  6 38  1  0  0  0  0
 38 39  1  6  0  0  0
  5 40  1  0  0  0  0
 40 41  2  0  0  0  0
  2 41  1  0  0  0  0
M  END

     RDKit          3D

 67 72  0  0  0  0  0  0  0  0999 V2000
    5.0583    4.8799   -1.0864 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5042    3.6055   -1.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3466    2.5269   -1.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8379    1.2698   -1.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4627    0.9827   -1.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0469   -0.4119   -1.1429 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6129   -1.1079   -0.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8612   -1.9124    0.8114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4998   -1.7384    0.8808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7186   -2.5424    1.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3256   -3.5313    2.4551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6790   -3.7169    2.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2680   -4.7012    3.1531 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4384   -2.9183    1.5867 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8170   -3.0554    1.4833 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8950   -0.6609    0.0486 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4444   -0.8708   -0.0472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2334    0.1856    0.3300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9162    0.0030    1.6773 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9800    0.0466    2.7192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8494    1.1267    1.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9362    1.7556    3.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8246    2.7947    3.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6449    3.2332    2.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5395    4.2843    2.4745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5435    2.5855    1.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3362    2.9692    0.0021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6505    1.5318    0.8972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5053    0.8525   -0.2782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2029    0.5014   -0.7596 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4377   -0.6832   -1.6704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1404   -1.7964   -1.2398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3722   -2.8817   -2.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9095   -2.8778   -3.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1113   -3.9263   -4.2628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2115   -1.7751   -3.8130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9868   -0.7086   -2.9699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6069   -0.7206   -1.2933 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0068    0.1437   -2.1740 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6353    2.0655   -1.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1529    3.3705   -1.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2398    5.3202   -0.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4329    2.6869   -1.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5467    0.4376   -1.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5696   -0.9267   -2.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437   -2.3974    1.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6712   -4.1464    3.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2663   -4.8867    3.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3907   -2.4921    0.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1799    0.3138    0.4912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5176    1.0424    0.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4781   -0.9374    1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1997    0.6071    2.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2933    1.4181    3.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9017    3.3024    4.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5809    4.7303    3.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9782    3.7329    0.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7913    1.2980   -1.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5114   -1.8239   -0.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9213   -3.7436   -1.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4596   -4.7038   -4.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8438   -1.7606   -4.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4440    0.1514   -3.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4451   -1.7556   -1.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4558    0.1271   -3.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5789    2.0026   -1.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4901    4.2260   -1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
 39 38  1  0
 38 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 34 36  1  0
 36 37  2  0
 16  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 41  1  0
 41 40  2  0
  8 14  1  0
 14 15  1  0
 14 12  2  0
 12 13  1  0
 12 11  1  0
 11 10  2  0
  6 38  1  0
 40  5  1  0
 30 18  1  0
 37 31  1  0
 10  9  1  0
 28 21  1  0
 39 65  1  0
 38 64  1  6
 16 50  1  1
 18 51  1  1
 19 52  1  6
 20 53  1  0
 22 54  1  0
 23 55  1  0
 25 56  1  0
 27 57  1  0
 30 58  1  6
 32 59  1  0
 33 60  1  0
 35 61  1  0
 36 62  1  0
 37 63  1  0
  6 45  1  6
  4 44  1  0
  3 43  1  0
  1 42  1  0
 41 67  1  0
 40 66  1  0
 15 49  1  0
 13 48  1  0
 11 47  1  0
 10 46  1  0
M  END


  Mrv1652309122207392D          

 41 46  0  0  1  0            999 V2000
    3.5724    3.7125    0.0000 O   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
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    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
   -1.4289    0.8250    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
   -2.1434    2.0625    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
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    3.5724   -1.2375    0.0000 C   0  0  0  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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 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    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5350    1.3237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  1  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 18 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 31 37  1  0  0  0  0
 16 38  1  0  0  0  0
  6 38  1  0  0  0  0
 38 39  1  6  0  0  0
  5 40  1  0  0  0  0
 40 41  2  0  0  0  0
  2 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0325129

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](O[C@@H]2[C@@H](O)C3=CC=C(O)C(O)=C3O[C@@H]2C2=CC=C(O)C=C2)C2=C(O[C@@H]1C1=CC=C(O)C=C1)C(O)=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O11/c31-15-5-1-13(2-6-15)25-24(38)29(18-10-12-20(34)23(37)28(18)39-25)41-30-21(35)17-9-11-19(33)22(36)27(17)40-26(30)14-3-7-16(32)8-4-14/h1-12,21,24-26,29-38H/t21-,24-,25+,26+,29-,30+/m0/s1

> <INCHI_KEY>
SFQDSEXKGVWBGB-WXMRMYLKSA-N

> <FORMULA>
C30H26O11

> <MOLECULAR_WEIGHT>
562.527

> <EXACT_MASS>
562.147511657

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
56.17582563245979

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S)-2-(4-hydroxyphenyl)-4-{[(2R,3R,4S)-4,7,8-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-3,4-dihydro-2H-1-benzopyran-3,7,8-triol

> <JCHEM_LOGP>
3.521055952333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.278902853264304

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.852852764197268

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6195801280386304

> <JCHEM_POLAR_SURFACE_AREA>
189.52999999999997

> <JCHEM_REFRACTIVITY>
142.94249999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S)-2-(4-hydroxyphenyl)-4-{[(2R,3R,4S)-4,7,8-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-3,4-dihydro-2H-1-benzopyran-3,7,8-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0       6.668   6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.334   3.850   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      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335   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       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       2.865   2.471   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   41                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   40                                                  
CONECT    6    5    7   38                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    8   15                                                  
CONECT   15   14                                                            
CONECT   16    9   17   38                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   30                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   21   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   18   31                                                  
CONECT   31   30   32   37                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   31                                                       
CONECT   38   16    6   39                                                  
CONECT   39   38                                                            
CONECT   40    5   41                                                       
CONECT   41   40    2                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₆O₁₁

Average Mass

562.5270 Da

Monoisotopic Mass

562.14751 Da

IUPAC Name

(2R,3R,4S)-2-(4-hydroxyphenyl)-4-{[(2R,3R,4S)-4,7,8-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-3,4-dihydro-2H-1-benzopyran-3,7,8-triol

Traditional Name

(2R,3R,4S)-2-(4-hydroxyphenyl)-4-{[(2R,3R,4S)-4,7,8-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-3,4-dihydro-2H-1-benzopyran-3,7,8-triol

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](O[C@@H]2[C@@H](O)C3=CC=C(O)C(O)=C3O[C@@H]2C2=CC=C(O)C=C2)C2=C(O[C@@H]1C1=CC=C(O)C=C1)C(O)=C(O)C=C2

InChI Identifier

InChI=1S/C30H26O11/c31-15-5-1-13(2-6-15)25-24(38)29(18-10-12-20(34)23(37)28(18)39-25)41-30-21(35)17-9-11-19(33)22(36)27(17)40-26(30)14-3-7-16(32)8-4-14/h1-12,21,24-26,29-38H/t21-,24-,25+,26+,29-,30+/m0/s1

InChI Key

SFQDSEXKGVWBGB-WXMRMYLKSA-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
Acacia caffra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as leucoanthocyanidins. These are flavonoids consisting of a flavan (3,4-dihydro-2-phenyl-2H-1-benzopyran) moiety that carries two hydroxy groups at the C3- and C4-positions.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Leucoanthocyanidins

Alternative Parents

Substituents

Leucoanthocyanidin-skeleton
3-hydroxyflavonoid
4'-hydroxyflavonoid
4-hydroxyflavonoid
7-hydroxyflavonoid
8-hydroxyflavonoid
Hydroxyflavonoid
Chromane
Benzopyran
1-benzopyran
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Polyol
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Alcohol
Organic oxygen compound
Hydrocarbon derivative
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
logP	3.52	ChemAxon
pKa (Strongest Acidic)	8.85	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	189.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	142.94 m³·mol⁻¹	ChemAxon
Polarizability	56.18 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162993558

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,4s)-2-(4-hydroxyphenyl)-4-{[(2r,3r,4s)-4,7,8-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-3,4-dihydro-2h-1-benzopyran-3,7,8-triol (NP0325129)

MOL for NP0325129 ((2r,3r,4s)-2-(4-hydroxyphenyl)-4-{[(2r,3r,4s)-4,7,8-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-3,4-dihydro-2h-1-benzopyran-3,7,8-triol)

3D MOL for NP0325129 ((2r,3r,4s)-2-(4-hydroxyphenyl)-4-{[(2r,3r,4s)-4,7,8-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-3,4-dihydro-2h-1-benzopyran-3,7,8-triol)

3D SDF for NP0325129 ((2r,3r,4s)-2-(4-hydroxyphenyl)-4-{[(2r,3r,4s)-4,7,8-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-3,4-dihydro-2h-1-benzopyran-3,7,8-triol)

3D-SDF for NP0325129 ((2r,3r,4s)-2-(4-hydroxyphenyl)-4-{[(2r,3r,4s)-4,7,8-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-3,4-dihydro-2h-1-benzopyran-3,7,8-triol)

PDB for NP0325129 ((2r,3r,4s)-2-(4-hydroxyphenyl)-4-{[(2r,3r,4s)-4,7,8-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-3,4-dihydro-2h-1-benzopyran-3,7,8-triol)

3D PDB for NP0325129 ((2r,3r,4s)-2-(4-hydroxyphenyl)-4-{[(2r,3r,4s)-4,7,8-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-3,4-dihydro-2h-1-benzopyran-3,7,8-triol)

SMILES for NP0325129 ((2r,3r,4s)-2-(4-hydroxyphenyl)-4-{[(2r,3r,4s)-4,7,8-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-3,4-dihydro-2h-1-benzopyran-3,7,8-triol)

INCHI for NP0325129 ((2r,3r,4s)-2-(4-hydroxyphenyl)-4-{[(2r,3r,4s)-4,7,8-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-3,4-dihydro-2h-1-benzopyran-3,7,8-triol)

Structure for NP0325129 ((2r,3r,4s)-2-(4-hydroxyphenyl)-4-{[(2r,3r,4s)-4,7,8-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-3,4-dihydro-2h-1-benzopyran-3,7,8-triol)

3D Structure for NP0325129 ((2r,3r,4s)-2-(4-hydroxyphenyl)-4-{[(2r,3r,4s)-4,7,8-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl]oxy}-3,4-dihydro-2h-1-benzopyran-3,7,8-triol)