NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate (NP0328612)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 12:14:17 UTC

Updated at

2022-09-12 12:14:17 UTC

NP-MRD ID

NP0328612

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate

Description

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton. [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate is found in Lysidice brevicalyx. Based on a literature review very few articles have been published on [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122214142D          

 39 42  0  0  1  0            999 V2000
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -12.3750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -13.6125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868  -14.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -15.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -14.0250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579  -14.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -13.6125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289  -14.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -12.7875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 O   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  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 22 28  1  0  0  0  0
 19 29  2  0  0  0  0
 14 29  1  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 10 34  1  0  0  0  0
 34 35  1  6  0  0  0
  5 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
  3 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END

     RDKit          3D

 67 70  0  0  0  0  0  0  0  0999 V2000
   -8.5230   -1.1979   -0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9773    0.0129   -0.1876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1846    0.8898    0.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8669    0.6910    0.8073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1118    1.5985    1.5195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6847    1.3273    1.7983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0793    2.2113    2.4469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0518    0.2056    1.3903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7042   -0.0801    1.6294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8490    0.9626    0.9465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4986    0.7379    1.1122 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1078   -0.1121    0.2319 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6020   -1.2277    0.9322 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9074   -1.6275    1.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1616   -2.7633    1.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4339   -3.2488    1.9833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6987   -4.3858    2.7382 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5365   -2.6080    1.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3059   -1.4878    0.6557 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4175   -0.7767    0.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6747   -1.0945    0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7772   -0.3756   -0.5461 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6072    0.7502   -1.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7055    1.3961   -1.8960 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9932    0.9380   -1.7311 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0627    1.6038   -2.3253 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1657   -0.1917   -0.9623 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0822   -0.8262   -0.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0028   -1.0220    0.4938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7299   -0.5147   -0.9580 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1831   -0.9548   -1.9431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3736    0.7316   -1.5114 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0273    0.5157   -2.7108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2936    1.2560   -0.4459 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5392    2.6165   -0.6737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7346    2.7489    1.9507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0674    2.9916    1.6834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7964    2.0612    0.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1375    2.2784    0.6832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7993   -2.0714   -0.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4458   -1.1968   -0.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1089   -1.3679   -1.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3787   -0.2131    0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4243   -1.1193    1.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775   -0.0061    2.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0321    1.9192    1.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9666    0.4466   -0.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3433   -3.2879    2.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6849   -5.2664    2.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5293   -3.0276    1.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1842    0.1230   -0.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9251   -1.9805    0.6758 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6129    1.1460   -1.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5463    2.2871   -2.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3584    1.3311   -3.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1669   -0.5612   -0.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2214   -1.7298    0.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8656   -0.1402   -0.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4092   -1.3450   -0.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2294   -1.6842   -2.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5545    1.4860   -1.6243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6366   -0.2941   -3.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2870    0.7445   -0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2724    2.7779   -1.3083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1994    3.5004    2.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5801    3.8887    2.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6647    1.6112    0.1686 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
  4  5  1  0
  5 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 19 29  2  0
 12 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 38  3  1  0
 34 10  1  0
 29 14  1  0
 28 22  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  4 43  1  0
 36 65  1  0
 37 66  1  0
 39 67  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  1
 12 47  1  6
 15 48  1  0
 17 49  1  0
 18 50  1  0
 20 51  1  0
 21 52  1  0
 23 53  1  0
 24 54  1  0
 26 55  1  0
 27 56  1  0
 28 57  1  0
 29 58  1  0
 30 59  1  1
 31 60  1  0
 32 61  1  6
 33 62  1  0
 34 63  1  6
 35 64  1  0
M  END


  Mrv1652309122214142D          

 39 42  0  0  1  0            999 V2000
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -12.3750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -13.6125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868  -14.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -11.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -15.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579  -14.0250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579  -14.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -13.6125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289  -14.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -12.7875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 O   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  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 22 28  1  0  0  0  0
 19 29  2  0  0  0  0
 14 29  1  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 10 34  1  0  0  0  0
 34 35  1  6  0  0  0
  5 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
  3 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328612

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C(=O)OC[C@H]1O[C@@H](OC2=CC(O)=CC(\C=C\C3=CC=C(O)C=C3)=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H28O11/c1-36-22-12-17(6-9-21(22)31)27(35)37-14-23-24(32)25(33)26(34)28(39-23)38-20-11-16(10-19(30)13-20)3-2-15-4-7-18(29)8-5-15/h2-13,23-26,28-34H,14H2,1H3/b3-2+/t23-,24-,25+,26-,28-/m1/s1

> <INCHI_KEY>
JFCVAWLHDBBPMF-LZRUTRTESA-N

> <FORMULA>
C28H28O11

> <MOLECULAR_WEIGHT>
540.521

> <EXACT_MASS>
540.163161722

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
53.76508408102539

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate

> <JCHEM_LOGP>
3.1683860543333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.93888441335157

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.453666933580651

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491104813948825

> <JCHEM_POLAR_SURFACE_AREA>
175.37

> <JCHEM_REFRACTIVITY>
137.86600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667 -16.940   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667 -18.480   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001 -19.250   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335 -18.480   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.001 -20.790   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.335 -21.560   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335 -23.100   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668 -23.870   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668 -25.410   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.002 -26.180   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.336 -25.410   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336 -23.870   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669 -23.100   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.669 -21.560   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.003 -23.870   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.003 -25.410   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.337 -26.180   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.670 -25.410   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.004 -26.180   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.338 -25.410   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.672 -26.180   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.672 -27.720   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      20.005 -28.490   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      17.338 -28.490   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.004 -27.720   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.669 -26.180   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335 -26.180   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.335 -27.720   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.001 -25.410   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.667 -26.180   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.001 -23.870   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.667 -23.100   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.334 -19.250   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.000 -18.480   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.000 -16.940   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -1.334 -16.170   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   38                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   36                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   34                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   30                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   29                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   29                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   22                                                       
CONECT   29   19   14                                                       
CONECT   30   12   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   10   35                                                  
CONECT   35   34                                                            
CONECT   36    5   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37    3   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-{3-hydroxy-5-[(e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoic acid	Generator

Chemical Formula

C₂₈H₂₈O₁₁

Average Mass

540.5210 Da

Monoisotopic Mass

540.16316 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate

Traditional Name

[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C(=O)OC[C@H]1O[C@@H](OC2=CC(O)=CC(\C=C\C3=CC=C(O)C=C3)=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C28H28O11/c1-36-22-12-17(6-9-21(22)31)27(35)37-14-23-24(32)25(33)26(34)28(39-23)38-20-11-16(10-19(30)13-20)3-2-15-4-7-18(29)8-5-15/h2-13,23-26,28-34H,14H2,1H3/b3-2+/t23-,24-,25+,26-,28-/m1/s1

InChI Key

JFCVAWLHDBBPMF-LZRUTRTESA-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
Lysidice brevicalyx	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Stilbene glycosides

Direct Parent

Stilbene glycosides

Alternative Parents

Substituents

Stilbene glycoside
Hydrolyzable tannin
Tannin
Phenolic glycoside
O-glycosyl compound
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
M-methoxybenzoic acid or derivatives
Glycosyl compound
Methoxyphenol
Benzoate ester
Benzoic acid or derivatives
Phenoxy compound
Phenol ether
Anisole
Styrene
Benzoyl
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Oxane
Monosaccharide
Secondary alcohol
Carboxylic acid ester
Polyol
Ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Acetal
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
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	3.17	ChemAxon
pKa (Strongest Acidic)	8.45	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	175.37 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	137.87 m³·mol⁻¹	ChemAxon
Polarizability	53.77 Å³	ChemAxon
Number of Rings	4	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

163188986

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate (NP0328612)

MOL for NP0328612 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate)

3D MOL for NP0328612 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate)

3D SDF for NP0328612 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate)

3D-SDF for NP0328612 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate)

PDB for NP0328612 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate)

3D PDB for NP0328612 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate)

SMILES for NP0328612 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate)

INCHI for NP0328612 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate)

Structure for NP0328612 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate)

3D Structure for NP0328612 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[(1e)-2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate)