NP-MRD: Showing NP-Card for 3-(acetyloxy)-6-[2-(3,5-dihydroxybenzoyl)-3,5-dihydroxyphenoxy]-5-hydroxy-2-methyloxan-4-yl benzoate (NP0232437)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 13:40:44 UTC

Updated at

2022-09-06 13:40:44 UTC

NP-MRD ID

NP0232437

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(acetyloxy)-6-[2-(3,5-dihydroxybenzoyl)-3,5-dihydroxyphenoxy]-5-hydroxy-2-methyloxan-4-yl benzoate

Description

3-(Acetyloxy)-6-[2-(3,5-dihydroxybenzoyl)-3,5-dihydroxyphenoxy]-5-hydroxy-2-methyloxan-4-yl benzoate belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. 3-(acetyloxy)-6-[2-(3,5-dihydroxybenzoyl)-3,5-dihydroxyphenoxy]-5-hydroxy-2-methyloxan-4-yl benzoate is found in Hypericum pseudopetiolatum. 3-(Acetyloxy)-6-[2-(3,5-dihydroxybenzoyl)-3,5-dihydroxyphenoxy]-5-hydroxy-2-methyloxan-4-yl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171511242D          

 40 43  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   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
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    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
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    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
    0.0000   -2.4750    0.0000 O   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
   -0.7145   -3.7125    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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 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
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 16 23  1  0  0  0  0
  4 24  1  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
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
 26 36  1  0  0  0  0
  2 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
M  END

     RDKit          3D

 66 69  0  0  0  0  0  0  0  0999 V2000
   -4.3838    1.4945    3.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1418    0.8311    2.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6743   -0.1664    3.2329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4150    1.2084    1.5613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2146    0.6105    1.0657 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0253    1.4279    1.3406 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2779    2.8192    1.8453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8510    1.4768    0.2966 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0576    0.3073   -0.4147 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6052   -0.6690    0.2558 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1570   -1.6345    0.9146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3378   -2.3732    1.8165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8556   -3.3985    2.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1182   -4.1716    3.4210 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1789   -3.7427    2.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0053   -3.0578    1.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3396   -3.4098    1.3671 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5004   -1.9822    0.7696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4331   -1.3512   -0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3664   -2.1191   -0.5999 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4834    0.0221   -0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0687    1.0825    0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1101    2.3931   -0.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6590    3.3826    0.6831 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5930    2.6687   -1.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0201    1.6408   -2.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5203    1.8568   -3.5191 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9678    0.3166   -1.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2206   -0.1365   -1.1014 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0273   -1.4151   -1.5969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3945   -0.1477   -0.1779 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5144    0.2472   -0.9476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4863   -0.6577   -1.2860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3661   -1.8454   -0.8994 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6632   -0.3082   -2.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6066   -1.2576   -2.3895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7082   -0.9135   -3.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9223    0.3671   -3.6118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9468    1.2877   -3.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8318    0.9820   -2.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0830    2.5641    3.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2163    1.4114    2.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6149    1.0852    4.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1179   -0.2240    1.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5723    0.9350    2.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4902    3.4891    1.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1444    2.8750    2.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2493    3.2326    1.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7291    0.5900   -1.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3025   -2.1026    1.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6551   -4.9960    3.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5983   -4.5683    2.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6796   -4.1877    1.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6911    0.8409    1.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2511    3.8501    1.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6436    3.6851   -1.7884 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4974    2.0053   -3.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3136   -0.4742   -2.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4077    0.4746   -2.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5573   -1.5954   -2.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5734   -1.2618    0.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5015   -2.3035   -2.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4532   -1.6851   -3.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8002    0.6437   -4.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0885    2.2980   -3.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0783    1.7534   -2.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
  9 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 33 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 31  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5  6  1  0
 18 11  1  0
 28 21  1  0
 40 35  1  0
  7 46  1  0
  7 47  1  0
  7 48  1  0
  6 45  1  1
  9 49  1  6
 12 50  1  0
 14 51  1  0
 15 52  1  0
 17 53  1  0
 22 54  1  0
 24 55  1  0
 25 56  1  0
 27 57  1  0
 28 58  1  0
 29 59  1  6
 30 60  1  0
 31 61  1  1
 36 62  1  0
 37 63  1  0
 38 64  1  0
 39 65  1  0
 40 66  1  0
  5 44  1  1
  1 41  1  0
  1 42  1  0
  1 43  1  0
M  END


  Mrv1533004171511242D          

 40 43  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   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
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    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
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    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
    0.0000   -2.4750    0.0000 O   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
   -0.7145   -3.7125    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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 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
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 16 23  1  0  0  0  0
  4 24  1  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
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
 26 36  1  0  0  0  0
  2 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0232437

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC2=CC(O)=CC(O)=C2C(=O)C2=CC(O)=CC(O)=C2)C(O)C(OC(=O)C2=CC=CC=C2)C1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H26O12/c1-13-25(38-14(2)29)26(40-27(36)15-6-4-3-5-7-15)24(35)28(37-13)39-21-12-19(32)11-20(33)22(21)23(34)16-8-17(30)10-18(31)9-16/h3-13,24-26,28,30-33,35H,1-2H3

> <INCHI_KEY>
BWQKZPYFEIFOEF-UHFFFAOYSA-N

> <FORMULA>
C28H26O12

> <MOLECULAR_WEIGHT>
554.504

> <EXACT_MASS>
554.142426277

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
52.969625254001585

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(acetyloxy)-6-[2-(3,5-dihydroxybenzoyl)-3,5-dihydroxyphenoxy]-5-hydroxy-2-methyloxan-4-yl benzoate

> <ALOGPS_LOGP>
3.79

> <JCHEM_LOGP>
4.280039377333334

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.369417590316283

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.09500813313191

> <JCHEM_PKA_STRONGEST_BASIC>
-3.969711307377451

> <JCHEM_POLAR_SURFACE_AREA>
189.27999999999997

> <JCHEM_REFRACTIVITY>
136.11220000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(acetyloxy)-6-[2-(3,5-dihydroxybenzoyl)-3,5-dihydroxyphenoxy]-5-hydroxy-2-methyloxan-4-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.669 -13.860   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   24                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    6   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   16                                                       
CONECT   24    4   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   36                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
CONECT   36   26    2   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Value	Source
3-(Acetyloxy)-6-[2-(3,5-dihydroxybenzoyl)-3,5-dihydroxyphenoxy]-5-hydroxy-2-methyloxan-4-yl benzoic acid	Generator

Chemical Formula

C₂₈H₂₆O₁₂

Average Mass

554.5040 Da

Monoisotopic Mass

554.14243 Da

IUPAC Name

3-(acetyloxy)-6-[2-(3,5-dihydroxybenzoyl)-3,5-dihydroxyphenoxy]-5-hydroxy-2-methyloxan-4-yl benzoate

Traditional Name

3-(acetyloxy)-6-[2-(3,5-dihydroxybenzoyl)-3,5-dihydroxyphenoxy]-5-hydroxy-2-methyloxan-4-yl benzoate

CAS Registry Number

Not Available

SMILES

CC1OC(OC2=CC(O)=CC(O)=C2C(=O)C2=CC(O)=CC(O)=C2)C(O)C(OC(=O)C2=CC=CC=C2)C1OC(C)=O

InChI Identifier

InChI=1S/C28H26O12/c1-13-25(38-14(2)29)26(40-27(36)15-6-4-3-5-7-15)24(35)28(37-13)39-21-12-19(32)11-20(33)22(21)23(34)16-8-17(30)10-18(31)9-16/h3-13,24-26,28,30-33,35H,1-2H3

InChI Key

BWQKZPYFEIFOEF-UHFFFAOYSA-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
Hypericum pseudopetiolatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Benzophenone
Aryl-phenylketone
Diphenylmethane
Hexose monosaccharide
O-glycosyl compound
Benzoate ester
Benzoic acid or derivatives
Phenoxy compound
Benzoyl
Aryl ketone
Resorcinol
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Monosaccharide
Oxane
Vinylogous acid
Ketone
Secondary alcohol
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Organic oxide
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	3.79	ALOGPS
logP	4.28	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	7.1	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	189.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	136.11 m³·mol⁻¹	ChemAxon
Polarizability	52.97 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(acetyloxy)-6-[2-(3,5-dihydroxybenzoyl)-3,5-dihydroxyphenoxy]-5-hydroxy-2-methyloxan-4-yl benzoate (NP0232437)

MOL for NP0232437 (3-(acetyloxy)-6-[2-(3,5-dihydroxybenzoyl)-3,5-dihydroxyphenoxy]-5-hydroxy-2-methyloxan-4-yl benzoate)

3D MOL for NP0232437 (3-(acetyloxy)-6-[2-(3,5-dihydroxybenzoyl)-3,5-dihydroxyphenoxy]-5-hydroxy-2-methyloxan-4-yl benzoate)

3D SDF for NP0232437 (3-(acetyloxy)-6-[2-(3,5-dihydroxybenzoyl)-3,5-dihydroxyphenoxy]-5-hydroxy-2-methyloxan-4-yl benzoate)

3D-SDF for NP0232437 (3-(acetyloxy)-6-[2-(3,5-dihydroxybenzoyl)-3,5-dihydroxyphenoxy]-5-hydroxy-2-methyloxan-4-yl benzoate)

PDB for NP0232437 (3-(acetyloxy)-6-[2-(3,5-dihydroxybenzoyl)-3,5-dihydroxyphenoxy]-5-hydroxy-2-methyloxan-4-yl benzoate)

3D PDB for NP0232437 (3-(acetyloxy)-6-[2-(3,5-dihydroxybenzoyl)-3,5-dihydroxyphenoxy]-5-hydroxy-2-methyloxan-4-yl benzoate)

SMILES for NP0232437 (3-(acetyloxy)-6-[2-(3,5-dihydroxybenzoyl)-3,5-dihydroxyphenoxy]-5-hydroxy-2-methyloxan-4-yl benzoate)

INCHI for NP0232437 (3-(acetyloxy)-6-[2-(3,5-dihydroxybenzoyl)-3,5-dihydroxyphenoxy]-5-hydroxy-2-methyloxan-4-yl benzoate)

Structure for NP0232437 (3-(acetyloxy)-6-[2-(3,5-dihydroxybenzoyl)-3,5-dihydroxyphenoxy]-5-hydroxy-2-methyloxan-4-yl benzoate)

3D Structure for NP0232437 (3-(acetyloxy)-6-[2-(3,5-dihydroxybenzoyl)-3,5-dihydroxyphenoxy]-5-hydroxy-2-methyloxan-4-yl benzoate)