NP-MRD: Showing NP-Card for Ligupurpurposide K (NP0044158)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2021-11-12 23:53:27 UTC

Updated at

2021-11-26 17:46:04 UTC

NP-MRD ID

NP0044158

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ligupurpurposide K

Description

(2S)-2beta-(beta-D-Glucopyranosyloxy)-5-carboxy-3,4-dihydro-2H-pyran-3alpha,4alpha-bisacetic acid 4-[2-(4-hydroxyphenyl)ethyl] ester belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. It was first documented in 2020 (PMID: 34756847). Based on a literature review a significant number of articles have been published on (2S)-2beta-(beta-D-Glucopyranosyloxy)-5-carboxy-3,4-dihydro-2H-pyran-3alpha,4alpha-bisacetic acid 4-[2-(4-hydroxyphenyl)ethyl] ester (PMID: 34758548) (PMID: 34758547) (PMID: 34758546) (PMID: 34758545).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100532D          

 38 40  0  0  1  0            999 V2000
    3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.0125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -8.2500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -8.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -8.2500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -7.0125    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
  2  4  2  0  0  0  0
  5  1  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
  8 19  2  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 20 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  6  0  0  0
 28 27  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 28 37  1  0  0  0  0
 37 38  1  1  0  0  0
M  END

     RDKit          3D

 68 70  0  0  0  0  0  0  0  0999 V2000
    1.3995   -0.4077    3.3552 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6450   -0.8282    2.4494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9733   -2.0160    1.8209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5670   -0.1130    2.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5186    0.5951    0.7352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9218    1.1928    0.5089 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4854    0.7310   -0.6653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7106    0.1210   -0.4486 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6091   -1.2167   -0.7216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7400   -1.9528   -0.4301 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7613   -3.3148   -1.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7142   -3.3069   -2.4514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0330   -1.2048   -0.5509 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4587   -0.7842    0.7310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9859   -0.0130   -1.4709 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9874   -0.4960   -2.7770 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7649    0.8403   -1.2274 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1778    1.9643   -0.5237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8318    2.6241    0.3555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0785    3.3097    1.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1769    2.8482    1.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0844    3.4341    2.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436    3.0102    2.5206 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6876    4.5080    3.1588 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4754    1.6715    0.5431 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9074    1.3949    0.4561 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3230    0.5002   -0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830   -0.5394   -0.8752 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4174    0.8139   -1.4239 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8284   -0.0252   -2.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3451   -1.3249   -1.8837 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5181   -1.0657   -1.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7944   -1.0493   -1.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9279   -0.7948   -0.8303 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7725   -0.5525    0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8834   -0.2922    1.3050 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5059   -0.5674    1.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3671   -0.8272    0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3879   -2.4585    1.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9958    0.5114    2.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3571   -0.9217    1.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4378   -0.1993   -0.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5264    0.9490    1.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9172    0.1935    0.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6257   -2.1948    0.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7069   -3.8055   -0.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8943   -3.9245   -0.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4423   -3.8309   -2.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8146   -1.9262   -0.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3977   -0.4770    0.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9229    0.5553   -1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6134   -1.2913   -2.7800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3840    1.1943   -2.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4186    2.7254   -1.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4107    4.1540    1.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7874    5.4572    2.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1996    2.1195   -0.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4173    1.0334    1.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4196    2.4081    0.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5473    0.4439   -3.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9166   -0.2550   -3.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5709   -1.8236   -1.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6220   -1.9787   -2.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8435   -1.2485   -2.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9139   -0.7906   -1.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7984   -0.2739    0.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4368   -0.3748    2.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3911   -0.8366    0.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  4  5  1  0
  5 25  1  0
 25 26  1  0
 26 27  1  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 35 37  1  0
 37 38  2  0
 27 28  2  0
 25 21  1  0
 21 22  1  0
 22 24  1  0
 22 23  2  0
 21 20  2  0
 20 19  1  0
 19  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  6  5  1  0
 38 32  1  0
 17  8  1  0
  4 40  1  0
  4 41  1  0
  3 39  1  0
  5 42  1  6
 25 57  1  6
 26 58  1  0
 26 59  1  0
 30 60  1  0
 30 61  1  0
 31 62  1  0
 31 63  1  0
 33 64  1  0
 34 65  1  0
 36 66  1  0
 37 67  1  0
 38 68  1  0
 24 56  1  0
 20 55  1  0
  6 43  1  1
  8 44  1  1
 10 45  1  1
 11 46  1  0
 11 47  1  0
 12 48  1  0
 13 49  1  6
 14 50  1  0
 15 51  1  6
 16 52  1  0
 17 53  1  6
 18 54  1  0
M  END


  Mrv1652311132100532D          

 38 40  0  0  1  0            999 V2000
    3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.0125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -8.2500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -8.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -8.2500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -7.0125    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
  2  4  2  0  0  0  0
  5  1  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
  8 19  2  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 20 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  6  0  0  0
 28 27  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 28 37  1  0  0  0  0
 37 38  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0044158

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H](CC(=O)OCCC3=CC=C(O)C=C3)[C@H]2CC(O)=O)C(O)=O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O14/c25-9-16-19(30)20(31)21(32)24(37-16)38-23-14(7-17(27)28)13(15(10-36-23)22(33)34)8-18(29)35-6-5-11-1-3-12(26)4-2-11/h1-4,10,13-14,16,19-21,23-26,30-32H,5-9H2,(H,27,28)(H,33,34)/t13-,14+,16+,19+,20-,21+,23-,24-/m0/s1

> <INCHI_KEY>
SBEDHFVHKZQSJG-ONNLFQHFSA-N

> <FORMULA>
C24H30O14

> <MOLECULAR_WEIGHT>
542.49

> <EXACT_MASS>
542.163555646

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
52.77365131388194

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S)-3-(carboxymethyl)-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid

> <ALOGPS_LOGP>
-0.24

> <JCHEM_LOGP>
-1.071353058666667

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.323527932738268

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6165032707908495

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981084760151578

> <JCHEM_POLAR_SURFACE_AREA>
229.73999999999995

> <JCHEM_REFRACTIVITY>
122.4158

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.38e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,5R,6S)-5-(carboxymethyl)-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.002 -10.780   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.336  -8.470   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.003  -3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.670  -3.850   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      13.337  -6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.667 -10.780   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.335 -10.780   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.668 -13.090   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.002 -13.860   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.002 -15.400   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.336 -16.170   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.669 -15.400   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.668 -17.710   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.335 -15.400   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       4.001 -13.090   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    1    6   26                                                  
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   12                                                       
CONECT   19    8                                                            
CONECT   20    6   21   24                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   20   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    5   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   37                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   28   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2b-(b-D-Glucopyranosyloxy)-5-carboxy-3,4-dihydro-2H-pyran-3a,4a-bisacetate 4-[2-(4-hydroxyphenyl)ethyl] ester	Generator
(2S)-2b-(b-D-Glucopyranosyloxy)-5-carboxy-3,4-dihydro-2H-pyran-3a,4a-bisacetic acid 4-[2-(4-hydroxyphenyl)ethyl] ester	Generator
(2S)-2beta-(beta-D-Glucopyranosyloxy)-5-carboxy-3,4-dihydro-2H-pyran-3alpha,4alpha-bisacetate 4-[2-(4-hydroxyphenyl)ethyl] ester	Generator
(2S)-2Β-(β-D-glucopyranosyloxy)-5-carboxy-3,4-dihydro-2H-pyran-3α,4α-bisacetate 4-[2-(4-hydroxyphenyl)ethyl] ester	Generator
(2S)-2Β-(β-D-glucopyranosyloxy)-5-carboxy-3,4-dihydro-2H-pyran-3α,4α-bisacetic acid 4-[2-(4-hydroxyphenyl)ethyl] ester	Generator

Chemical Formula

C₂₄H₃₀O₁₄

Average Mass

542.4900 Da

Monoisotopic Mass

542.16356 Da

IUPAC Name

(2S,3R,4S)-3-(carboxymethyl)-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid

Traditional Name

(4S,5R,6S)-5-(carboxymethyl)-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H](CC(=O)OCCC3=CC=C(O)C=C3)[C@H]2CC(O)=O)C(O)=O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C24H30O14/c25-9-16-19(30)20(31)21(32)24(37-16)38-23-14(7-17(27)28)13(15(10-36-23)22(33)34)8-18(29)35-6-5-11-1-3-12(26)4-2-11/h1-4,10,13-14,16,19-21,23-26,30-32H,5-9H2,(H,27,28)(H,33,34)/t13-,14+,16+,19+,20-,21+,23-,24-/m0/s1

InChI Key

SBEDHFVHKZQSJG-ONNLFQHFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Ligustrum purpurascens

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
O-glycosyl compound
Secoiridoid-skeleton
Glycosyl compound
Tyrosol derivative
Monoterpenoid
Monocyclic monoterpenoid
Aromatic monoterpenoid
Tricarboxylic acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Sugar acid
Phenol
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Vinylogous ester
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	-0.24	ALOGPS
logP	-1.1	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.62	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	229.74 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	122.42 m³·mol⁻¹	ChemAxon
Polarizability	52.77 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

122383066

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

McDonagh MS, Wagner J, Ahmed AY, Morasco B, Kansagara D, Chou R: Living Systematic Review on Cannabis and Other Plant-Based Treatments for Chronic Pain - Quarterly Progress Report/Addendum: September 2021. 2020 Dec. [PubMed:34756847 ]
Zhang WB, Yang QB, Wu SF, Lu SH, Cheng M, Sheng Y, Zhang QC, Yang LF, Yu L, Yan SX: [Application of diffusion-weighted magnetic resonance imaging in evaluating the efficacy of radiotherapy and chemotherapy for esophageal cancer]. Zhonghua Yi Xue Za Zhi. 2021 Nov 9;101(41):3427-3430. doi: 10.3760/cma.j.cn112137-20210709-01544. [PubMed:34758548 ]
Sun Y, Wang DM, Yu H, Liu C, Ji TY, Wang S, Wu Y, Liu XY, Jiang YW, Cai LX, Liu QZ: [The screening of potential biological markers of seizure onset zone in focal cortical dysplasia based on bioinformatics analysis]. Zhonghua Yi Xue Za Zhi. 2021 Nov 9;101(41):3422-3426. doi: 10.3760/cma.j.cn112137-20210331-00779. [PubMed:34758547 ]
Dong HH, Cai YS, Liang XN, Miao JB, Chen QS, Gao YD, Li H: [Analysis of incidence and risk factors for postoperative venous thromboembolism in patients with stage a non-small-cell lung cancer]. Zhonghua Yi Xue Za Zhi. 2021 Nov 9;101(41):3417-3421. doi: 10.3760/cma.j.cn112137-20210418-00929. [PubMed:34758546 ]
Chai YR, Gao JB, Lyu PJ, Liang P, Xing JJ, Liu J: [Comparative study of CT relative enhancement value and subjective visual evaluation for intestinal ischemia in patients with closed loop obstruction]. Zhonghua Yi Xue Za Zhi. 2021 Nov 9;101(41):3411-3416. doi: 10.3760/cma.j.cn112137-20210328-00756. [PubMed:34758545 ]
Long Fan et al. (2015). Phenylethanoid and secoiridoid glycosides from the leaves of Ligustrum purpurascens. Phytochemistry Letters, Volume 13, September 2015, Pages 177-181. DOI: 10.1016/j.phytol.2015.06.011. Phytochemistry Letters.

Showing NP-Card for Ligupurpurposide K (NP0044158)

MOL for NP0044158 (Ligupurpurposide K)

3D MOL for NP0044158 (Ligupurpurposide K)

3D SDF for NP0044158 (Ligupurpurposide K)

3D-SDF for NP0044158 (Ligupurpurposide K)

PDB for NP0044158 (Ligupurpurposide K)

3D PDB for NP0044158 (Ligupurpurposide K)

SMILES for NP0044158 (Ligupurpurposide K)

INCHI for NP0044158 (Ligupurpurposide K)

Structure for NP0044158 (Ligupurpurposide K)

3D Structure for NP0044158 (Ligupurpurposide K)