NP-MRD: Showing NP-Card for [(1s,2s,4s,5s,6r,10s)-10-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy}-5-hydroxy-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl 3,4-dimethoxybenzoate (NP0319808)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 21:02:23 UTC

Updated at

2022-09-11 21:02:23 UTC

NP-MRD ID

NP0319808

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s,2s,4s,5s,6r,10s)-10-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy}-5-hydroxy-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl 3,4-dimethoxybenzoate

Description

Pakiside B 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. Based on a literature review very few articles have been published on Pakiside B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112223022D          

 38 42  0  0  1  0            999 V2000
    6.0394    5.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0141    4.3051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2873    3.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2619    3.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5351    2.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8336    3.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1068    2.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4054    3.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0815    1.9191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3547    1.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    0.7042    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1467    0.5928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6415   -0.0595    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0118   -0.5924    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0727   -1.4151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3103   -0.1581    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5182   -0.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0776    0.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1186    0.9831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9107    1.2138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1070    2.0151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5111    2.5858    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2810    2.3550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8768    2.9257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6689    2.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8651    1.8936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805    3.7270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2764    4.2976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1115    3.9577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3078    4.7590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7074    3.3871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4995    3.6178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6957    4.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5066    0.6432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8590    3.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5858    4.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6112    5.1737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3380    5.5640    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 20 34  1  0  0  0  0
 16 34  1  0  0  0  0
 34 11  1  6  0  0  0
  6 35  1  0  0  0  0
 35 36  2  0  0  0  0
  3 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END

     RDKit          3D

 70 74  0  0  0  0  0  0  0  0999 V2000
    7.6400   -3.5870    2.9597 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4831   -2.2191    2.6838 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2687   -1.6715    2.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1586   -2.4785    2.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9535   -1.9394    1.7418 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7884   -0.5996    1.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4878   -0.0883    1.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5242   -0.9174    0.9792 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2127    1.2202    0.7323 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9006    1.6453    0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0648    1.5650    1.4781 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2160    2.4347    2.5397 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2274    0.9861    2.7283 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0251    0.6172    3.5050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0858    1.3353    4.7047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1394    1.1598    2.6139 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2572    0.2130    2.7497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2553   -0.8919    2.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1719   -1.0520    1.1809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8091    0.1152    0.4112 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8568    0.4223   -0.4784 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5344    0.1722   -1.8090 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6558    1.2905   -2.5977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3112    1.1446   -3.7860 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3706    2.5440   -4.4238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0335    2.5142   -5.6430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7569    0.7045   -3.6683 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2009    0.1801   -4.8860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8811   -0.2716   -2.5407 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2914    0.4470   -1.3896 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5181   -0.8772   -2.2946 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0957   -1.4754   -3.4731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9952   -2.8582   -3.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5458    1.3026    1.2544 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9032    0.1975    1.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1268   -0.3301    2.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2698    0.4648    2.1543 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2636    1.8433    1.9187 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6063   -3.7447    3.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5595   -4.2469    2.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8549   -3.9293    3.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2581   -3.5370    2.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1085   -2.6343    1.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5922    0.9491   -0.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0440    2.6813   -0.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1958    0.6086    3.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1144   -0.4612    3.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3746    2.0429    4.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4353    2.1952    2.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0426    0.4740    3.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0761   -1.5999    2.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -0.2338   -0.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5063   -0.2165   -1.8564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7578    0.5322   -4.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3695    2.9809   -4.4644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9865    3.1942   -3.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9010    1.6899   -6.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3967    1.6042   -3.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4881   -0.7504   -4.7741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5850   -1.1105   -2.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0378    1.3907   -1.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6635   -1.6754   -1.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6655   -3.3649   -4.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9129   -3.3105   -2.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2085   -3.0066   -2.5186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9317    2.2068    0.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8413    1.2655    1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6729    2.0909    1.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2863    2.2325    1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8502    2.4205    2.7944 H   0  0  0  0  0  0  0  0  0  0  0  0
 33 32  1  0
 32 31  1  0
 31 22  1  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 14  1  0
 14 15  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  6
 10  9  1  0
  9  7  1  0
  7  8  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  3 36  1  0
 36 37  1  0
 37 38  1  0
 36 35  2  0
 11 34  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 34 20  1  0
 34 16  1  0
 11 13  1  0
 35  6  1  0
 33 63  1  0
 33 64  1  0
 33 65  1  0
 31 62  1  1
 22 53  1  1
 20 52  1  6
 18 51  1  0
 17 50  1  0
 16 49  1  1
 14 47  1  1
 15 48  1  0
 13 46  1  6
 10 44  1  0
 10 45  1  0
  5 43  1  0
  4 42  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
 38 68  1  0
 38 69  1  0
 38 70  1  0
 35 67  1  0
 34 66  1  6
 24 54  1  6
 25 55  1  0
 25 56  1  0
 26 57  1  0
 27 58  1  1
 28 59  1  0
 29 60  1  6
 30 61  1  0
M  END


  Mrv1652309112223022D          

 38 42  0  0  1  0            999 V2000
    6.0394    5.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0141    4.3051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2873    3.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2619    3.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5351    2.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8336    3.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1068    2.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4054    3.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0815    1.9191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3547    1.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    0.7042    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1467    0.5928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6415   -0.0595    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0118   -0.5924    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0727   -1.4151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3103   -0.1581    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5182   -0.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0776    0.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1186    0.9831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9107    1.2138    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1070    2.0151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5111    2.5858    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2810    2.3550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8768    2.9257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6689    2.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8651    1.8936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805    3.7270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2764    4.2976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1115    3.9577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3078    4.7590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7074    3.3871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4995    3.6178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6957    4.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5066    0.6432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8590    3.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5858    4.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6112    5.1737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3380    5.5640    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 20 34  1  0  0  0  0
 16 34  1  0  0  0  0
 34 11  1  6  0  0  0
  6 35  1  0  0  0  0
 35 36  2  0  0  0  0
  3 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0319808

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1[C@H](O[C@@H]2OC=C[C@H]3[C@H](O)[C@@H]4O[C@]4(COC(=O)C4=CC=C(OC)C(OC)=C4)[C@@H]23)O[C@H](CO)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O13/c1-31-13-5-4-11(8-14(13)32-2)22(30)35-10-25-16-12(17(27)21(25)38-25)6-7-34-23(16)37-24-20(33-3)19(29)18(28)15(9-26)36-24/h4-8,12,15-21,23-24,26-29H,9-10H2,1-3H3/t12-,15-,16-,17+,18-,19+,20-,21+,23+,24+,25-/m1/s1

> <INCHI_KEY>
DRDAENUBFJKSDP-VFWWIDFWSA-N

> <FORMULA>
C25H32O13

> <MOLECULAR_WEIGHT>
540.518

> <EXACT_MASS>
540.18429109

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
52.80216447672559

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,2S,4S,5S,6R,10S)-10-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy}-5-hydroxy-3,9-dioxatricyclo[4.4.0.0^{2,4}]dec-7-en-2-yl]methyl 3,4-dimethoxybenzoate

> <JCHEM_LOGP>
-0.6087197886666669

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.615432544602207

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.673505176051464

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810849638064347

> <JCHEM_POLAR_SURFACE_AREA>
175.13

> <JCHEM_REFRACTIVITY>
124.69110000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2S,4S,5S,6R,10S)-10-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy}-5-hydroxy-3,9-dioxatricyclo[4.4.0.0^{2,4}]dec-7-en-2-yl]methyl 3,4-dimethoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      11.274   9.576   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.226   8.036   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.870   7.308   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.822   5.768   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.466   5.040   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.156   5.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.799   5.122   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.490   5.932   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       5.752   3.582   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.395   2.854   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.348   1.314   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.874   1.107   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.931  -0.111   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.755  -1.106   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.869  -2.642   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.446  -0.295   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.967  -0.726   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.145   0.339   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.221   1.835   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.700   2.266   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.066   3.762   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.954   4.827   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.524   4.396   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.637   5.461   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.115   5.031   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.482   3.535   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.270   6.957   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.383   8.022   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.208   7.388   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.575   8.883   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.320   6.323   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.799   6.753   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.165   8.249   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.812   1.201   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.203   7.390   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.560   8.118   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.607   9.658   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       9.964  10.386   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   35                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   34                                             
CONECT   12   11   13                                                       
CONECT   13   12   11   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   34                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   34                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   22   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   20   16   11                                                  
CONECT   35    6   36                                                       
CONECT   36   35    3   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₂O₁₃

Average Mass

540.5180 Da

Monoisotopic Mass

540.18429 Da

IUPAC Name

[(1S,2S,4S,5S,6R,10S)-10-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy}-5-hydroxy-3,9-dioxatricyclo[4.4.0.0^{2,4}]dec-7-en-2-yl]methyl 3,4-dimethoxybenzoate

Traditional Name

[(1S,2S,4S,5S,6R,10S)-10-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy}-5-hydroxy-3,9-dioxatricyclo[4.4.0.0^{2,4}]dec-7-en-2-yl]methyl 3,4-dimethoxybenzoate

CAS Registry Number

Not Available

SMILES

CO[C@H]1[C@H](O[C@@H]2OC=C[C@H]3[C@H](O)[C@@H]4O[C@]4(COC(=O)C4=CC=C(OC)C(OC)=C4)[C@@H]23)O[C@H](CO)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C25H32O13/c1-31-13-5-4-11(8-14(13)32-2)22(30)35-10-25-16-12(17(27)21(25)38-25)6-7-34-23(16)37-24-20(33-3)19(29)18(28)15(9-26)36-24/h4-8,12,15-21,23-24,26-29H,9-10H2,1-3H3/t12-,15-,16-,17+,18-,19+,20-,21+,23+,24+,25-/m1/s1

InChI Key

DRDAENUBFJKSDP-VFWWIDFWSA-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

Not Available

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
Glycosyl compound
M-methoxybenzoic acid or derivatives
O-glycosyl compound
P-methoxybenzoic acid or derivatives
O-dimethoxybenzene
Dimethoxybenzene
Benzoate ester
Benzoic acid or derivatives
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Benzoyl
Alkyl aryl ether
Oxane
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Dialkyl ether
Oxirane
Ether
Primary alcohol
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxygen 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	-0.61	ChemAxon
pKa (Strongest Acidic)	12.67	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	175.13 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	124.69 m³·mol⁻¹	ChemAxon
Polarizability	52.8 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

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

102258263

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1s,2s,4s,5s,6r,10s)-10-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy}-5-hydroxy-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl 3,4-dimethoxybenzoate (NP0319808)

MOL for NP0319808 ([(1s,2s,4s,5s,6r,10s)-10-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy}-5-hydroxy-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl 3,4-dimethoxybenzoate)

3D MOL for NP0319808 ([(1s,2s,4s,5s,6r,10s)-10-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy}-5-hydroxy-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl 3,4-dimethoxybenzoate)

3D SDF for NP0319808 ([(1s,2s,4s,5s,6r,10s)-10-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy}-5-hydroxy-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl 3,4-dimethoxybenzoate)

3D-SDF for NP0319808 ([(1s,2s,4s,5s,6r,10s)-10-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy}-5-hydroxy-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl 3,4-dimethoxybenzoate)

PDB for NP0319808 ([(1s,2s,4s,5s,6r,10s)-10-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy}-5-hydroxy-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl 3,4-dimethoxybenzoate)

3D PDB for NP0319808 ([(1s,2s,4s,5s,6r,10s)-10-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy}-5-hydroxy-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl 3,4-dimethoxybenzoate)

SMILES for NP0319808 ([(1s,2s,4s,5s,6r,10s)-10-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy}-5-hydroxy-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl 3,4-dimethoxybenzoate)

INCHI for NP0319808 ([(1s,2s,4s,5s,6r,10s)-10-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy}-5-hydroxy-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl 3,4-dimethoxybenzoate)

Structure for NP0319808 ([(1s,2s,4s,5s,6r,10s)-10-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy}-5-hydroxy-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl 3,4-dimethoxybenzoate)

3D Structure for NP0319808 ([(1s,2s,4s,5s,6r,10s)-10-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-methoxyoxan-2-yl]oxy}-5-hydroxy-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-2-yl]methyl 3,4-dimethoxybenzoate)