NP-MRD: Showing NP-Card for methyl 4-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dimethoxybenzoate (NP0231875)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 12:54:49 UTC

Updated at

2022-09-06 12:54:49 UTC

NP-MRD ID

NP0231875

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dimethoxybenzoate

Description

3,5-Dimethoxy-4-[(2-O-D-apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy]benzoic acid methyl ester belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. methyl 4-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dimethoxybenzoate is found in Albizia julibrissin. Based on a literature review very few articles have been published on 3,5-Dimethoxy-4-[(2-O-D-apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy]benzoic acid methyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062214542D          

 35 37  0  0  1  0            999 V2000
    8.5780   -5.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0931   -4.8027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2726   -4.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9371   -5.6426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7877   -4.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9672   -4.3077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4823   -3.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6618   -3.7265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3262   -4.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8178   -2.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -2.2192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5124   -2.3054    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1769   -3.0591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3564   -3.1453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0208   -3.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2004   -3.9852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8715   -2.4779    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0510   -2.5641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2070   -1.7242    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7221   -1.0568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0275   -1.6380    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3631   -0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8781   -0.2169    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0531   -0.2169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7982    0.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.0527    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9136    1.6658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0177    1.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7627    2.4504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1331    0.5678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9177    0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6383   -2.8004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9739   -2.0467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7944   -1.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1232   -3.4678    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  1  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  6  0  0  0
 28 29  1  0  0  0  0
 26 30  1  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  1  0  0  0
 10 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  2  0  0  0  0
  5 35  1  0  0  0  0
M  END

     RDKit          3D

 65 67  0  0  0  0  0  0  0  0999 V2000
    8.0687    2.1077    0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8598    1.3771    0.7214 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8987    1.6602   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1232    2.5540   -1.0680 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6467    0.9158   -0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6482    1.1687   -1.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4650    0.4431   -1.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4991    0.7301   -2.0868 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7033    1.7307   -3.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2388   -0.5401   -0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0640   -1.2823   -0.1414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0439   -0.8637    0.6327 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2496   -1.8109    1.5910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3905   -2.5173    1.5778 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0964   -3.8689    2.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2368   -4.6356    2.2658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0248   -2.8127    0.2750 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4143   -2.6370    0.4046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5702   -1.9829   -0.8774 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4690   -2.5272   -1.5341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2128   -0.6171   -0.2744 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3407   -0.2508    0.4828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7881    0.9599    0.0399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9992    1.8978    1.0495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6598    2.9429    0.4282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4538    2.3813   -0.7066 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9054    2.7147   -1.9440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9220    2.7102   -0.6146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6843    2.0553   -1.5475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2110    0.8789   -0.5339 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2288    0.2145   -1.7370 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2105   -0.8013    0.7364 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0518   -1.7832    1.7204 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0688   -2.0251    2.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3782   -0.0738    0.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8927    3.1445    0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7931    1.5845    0.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4720    2.2315    1.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8571    1.9417   -1.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9581    1.6586   -3.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6581    2.7607   -2.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7158    1.5523   -3.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2352    0.1006    1.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1216   -2.0211    2.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6900   -3.6581    3.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2586   -4.3359    1.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9996   -5.5961    2.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9088   -3.8925   -0.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8771   -2.7925   -0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4130   -1.8766   -1.5909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3127   -3.4732   -1.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9532    0.1240   -1.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1743    1.3771   -0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3083    3.5100    1.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8741    3.6645    0.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6541    2.9436   -2.5500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0117    3.8059   -0.7604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2311    2.5085    0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6021    1.9926   -1.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9250    0.4774    0.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3834    0.4358   -2.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9592   -2.4135    2.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6726   -2.7954    3.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3182   -1.0909    3.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1433   -0.2808    1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  6
 26 28  1  0
 28 29  1  0
 26 30  1  0
 30 31  1  0
 10 32  1  0
 32 33  1  0
 33 34  1  0
 32 35  2  0
 35  5  1  0
 21 12  1  0
 30 23  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  6 39  1  0
  9 40  1  0
  9 41  1  0
  9 42  1  0
 12 43  1  1
 14 44  1  1
 15 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  6
 18 49  1  0
 19 50  1  6
 20 51  1  0
 21 52  1  6
 23 53  1  6
 25 54  1  0
 25 55  1  0
 27 56  1  0
 28 57  1  0
 28 58  1  0
 29 59  1  0
 30 60  1  1
 31 61  1  0
 34 62  1  0
 34 63  1  0
 34 64  1  0
 35 65  1  0
M  END


  Mrv1652309062214542D          

 35 37  0  0  1  0            999 V2000
    8.5780   -5.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0931   -4.8027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2726   -4.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9371   -5.6426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7877   -4.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9672   -4.3077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4823   -3.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6618   -3.7265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3262   -4.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8178   -2.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -2.2192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5124   -2.3054    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1769   -3.0591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3564   -3.1453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0208   -3.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2004   -3.9852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8715   -2.4779    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0510   -2.5641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2070   -1.7242    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7221   -1.0568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0275   -1.6380    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3631   -0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8781   -0.2169    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0531   -0.2169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7982    0.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.0527    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9136    1.6658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0177    1.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7627    2.4504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1331    0.5678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9177    0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6383   -2.8004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9739   -2.0467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7944   -1.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1232   -3.4678    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  1  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  6  0  0  0
 28 29  1  0  0  0  0
 26 30  1  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  1  0  0  0
 10 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  2  0  0  0  0
  5 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0231875

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC(OC)=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@@H]2OC[C@](O)(CO)[C@H]2O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O14/c1-29-10-4-9(18(27)31-3)5-11(30-2)15(10)34-19-16(14(25)13(24)12(6-22)33-19)35-20-17(26)21(28,7-23)8-32-20/h4-5,12-14,16-17,19-20,22-26,28H,6-8H2,1-3H3/t12-,13-,14+,16-,17+,19+,20+,21-/m1/s1

> <INCHI_KEY>
VJJIKWUIJVQWMQ-URDJIEABSA-N

> <FORMULA>
C21H30O14

> <MOLECULAR_WEIGHT>
506.457

> <EXACT_MASS>
506.163555646

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
48.80910396986238

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 4-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dimethoxybenzoate

> <JCHEM_LOGP>
-2.1867522263333337

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.6520964218026

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.807561868214085

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092591790901

> <JCHEM_POLAR_SURFACE_AREA>
203.05999999999997

> <JCHEM_REFRACTIVITY>
111.8052

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dimethoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      16.012 -10.211   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      15.107  -8.965   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      13.576  -9.126   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.949 -10.533   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      12.670  -7.880   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.139  -8.041   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.234  -6.795   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.702  -6.956   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.076  -8.363   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.860  -5.388   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.955  -4.142   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.423  -4.303   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.797  -5.710   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.265  -5.871   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.639  -7.278   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.107  -7.439   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.360  -4.625   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.829  -4.786   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.986  -3.219   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.081  -1.973   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.518  -3.058   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.144  -1.651   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.239  -0.405   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.699  -0.405   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.223   1.060   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.469   1.965   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.439   3.109   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.500   3.109   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.024   4.574   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.715   1.060   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.180   1.536   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.392  -5.227   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.018  -3.821   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      14.549  -3.660   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.297  -6.473   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   35                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11   32                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   12   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28   30                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   26   23   31                                                  
CONECT   31   30                                                            
CONECT   32   10   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32    5                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
3,5-Dimethoxy-4-[(2-O-D-apio-b-D-furanosyl-b-D-glucopyranosyl)oxy]benzoate methyl ester	Generator
3,5-Dimethoxy-4-[(2-O-D-apio-b-D-furanosyl-b-D-glucopyranosyl)oxy]benzoic acid methyl ester	Generator
3,5-Dimethoxy-4-[(2-O-D-apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy]benzoate methyl ester	Generator
3,5-Dimethoxy-4-[(2-O-D-apio-β-D-furanosyl-β-D-glucopyranosyl)oxy]benzoate methyl ester	Generator
3,5-Dimethoxy-4-[(2-O-D-apio-β-D-furanosyl-β-D-glucopyranosyl)oxy]benzoic acid methyl ester	Generator

Chemical Formula

C₂₁H₃₀O₁₄

Average Mass

506.4570 Da

Monoisotopic Mass

506.16356 Da

IUPAC Name

methyl 4-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dimethoxybenzoate

Traditional Name

methyl 4-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dimethoxybenzoate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC(OC)=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@@H]2OC[C@](O)(CO)[C@H]2O)C(OC)=C1

InChI Identifier

InChI=1S/C21H30O14/c1-29-10-4-9(18(27)31-3)5-11(30-2)15(10)34-19-16(14(25)13(24)12(6-22)33-19)35-20-17(26)21(28,7-23)8-32-20/h4-5,12-14,16-17,19-20,22-26,28H,6-8H2,1-3H3/t12-,13-,14+,16-,17+,19+,20+,21-/m1/s1

InChI Key

VJJIKWUIJVQWMQ-URDJIEABSA-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
Albizia julibrissin	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Phenolic glycoside
Gallic acid or derivatives
O-glycosyl compound
Disaccharide
M-methoxybenzoic acid or derivatives
Glycosyl compound
M-dimethoxybenzene
Dimethoxybenzene
Benzoate ester
Benzoic acid or derivatives
Phenoxy compound
Anisole
Phenol ether
Benzoyl
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Oxane
Benzenoid
Methyl ester
Tertiary alcohol
Oxolane
Secondary alcohol
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Alcohol
Organic oxygen compound
Primary alcohol
Organic oxide
Organooxygen compound
Hydrocarbon derivative
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	-2.2	ChemAxon
pKa (Strongest Acidic)	11.81	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	203.06 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	111.81 m³·mol⁻¹	ChemAxon
Polarizability	48.81 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

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

101615538

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 4-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dimethoxybenzoate (NP0231875)

MOL for NP0231875 (methyl 4-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dimethoxybenzoate)

3D MOL for NP0231875 (methyl 4-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dimethoxybenzoate)

3D SDF for NP0231875 (methyl 4-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dimethoxybenzoate)

3D-SDF for NP0231875 (methyl 4-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dimethoxybenzoate)

PDB for NP0231875 (methyl 4-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dimethoxybenzoate)

3D PDB for NP0231875 (methyl 4-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dimethoxybenzoate)

SMILES for NP0231875 (methyl 4-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dimethoxybenzoate)

INCHI for NP0231875 (methyl 4-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dimethoxybenzoate)

Structure for NP0231875 (methyl 4-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dimethoxybenzoate)

3D Structure for NP0231875 (methyl 4-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dimethoxybenzoate)