NP-MRD: Showing NP-Card for methyl (5e)-5-[2-(acetyloxy)ethylidene]-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate (NP0217423)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 17:46:08 UTC

Updated at

2022-09-05 17:46:08 UTC

NP-MRD ID

NP0217423

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (5e)-5-[2-(acetyloxy)ethylidene]-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate

Description

10-Acetoxyligustroside 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. 10-Acetoxyligustroside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 10-Acetoxyligustroside has been detected, but not quantified in, herbs and spices. methyl (5e)-5-[2-(acetyloxy)ethylidene]-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate is found in Osmanthus fortunei, Osmanthus fragrans and Osmanthus heterophyllus. This could make 10-acetoxyligustroside a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308182D          

 41 43  0  0  0  0            999 V2000
    1.9533   10.5835    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
    0.0000    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.0125    0.0000 C   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    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7035    8.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9066    8.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5367   10.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3336   10.2136    0.0000 O   0  0  0  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    8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   11.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 O   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
    2.3232    9.2032    0.0000 O   0  0  0  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
    5.7158    8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 14  1  1  0  0  0  0
 15  3  2  0  0  0  0
 15  4  1  0  0  0  0
 15  7  1  0  0  0  0
 16  5  2  0  0  0  0
 16  6  1  0  0  0  0
 17  8  2  0  0  0  0
 18 11  1  0  0  0  0
 18 17  1  0  0  0  0
 19 13  2  0  0  0  0
 19 18  1  0  0  0  0
 20 12  1  0  0  0  0
 21 11  1  0  0  0  0
 22 20  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 19  1  0  0  0  0
 26 17  1  0  0  0  0
 27 24  1  0  0  0  0
 28 12  1  0  0  0  0
 29 14  2  0  0  0  0
 30 16  1  0  0  0  0
 31 21  2  0  0  0  0
 32 22  1  0  0  0  0
 33 23  1  0  0  0  0
 34 24  1  0  0  0  0
 35 25  2  0  0  0  0
 36  2  1  0  0  0  0
 36 25  1  0  0  0  0
 37 10  1  0  0  0  0
 37 14  1  0  0  0  0
 38  9  1  0  0  0  0
 38 21  1  0  0  0  0
 39 13  1  0  0  0  0
 39 26  1  0  0  0  0
 40 20  1  0  0  0  0
 40 27  1  0  0  0  0
 41 26  1  0  0  0  0
 41 27  1  0  0  0  0
M  END

     RDKit          3D

 75 77  0  0  0  0  0  0  0  0999 V2000
    2.4865   -2.4642    4.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6066   -1.6211    3.6126 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4814   -1.7797    2.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2041   -2.6881    1.7600 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5691   -0.9067    1.4651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1156   -0.0397    2.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0075    0.8022    1.6289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8969    0.0784    0.6990 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7566    1.0387    0.2880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1027    0.8306    0.5005 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7009    0.7971   -0.7557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0628    0.6862   -0.7481 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4960    0.5003   -2.2091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0924    1.6001   -2.9527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6670    1.9735   -0.2359 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.5583    1.6240    0.7928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5683    2.8468    0.3645 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8079    3.3671   -0.6739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7659    1.9397    1.2673 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6434    1.3802    2.1923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9221   -0.3764   -0.3858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2690   -0.2592   -1.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4863   -0.6276   -2.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0687   -1.5776   -3.6622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5429   -2.8121   -3.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1127   -3.6288   -4.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5109   -3.2878   -2.2676 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3764   -0.8600    0.0019 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0929   -1.9232   -0.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5900   -1.7360   -0.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3280   -2.6520   -1.0072 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1761   -0.6028   -0.0626 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5696   -0.3875    0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7801    0.9721    0.6797 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2422    1.1905    0.7994 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9826    1.7812   -0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3402    1.9682   -0.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9551    1.5502    1.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3206    1.7643    1.2292 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2428    0.9543    2.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8822    0.7841    1.9580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5600   -3.4293    3.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5278   -2.0456    4.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1300   -2.6798    5.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0532   -0.0292    3.3545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3229   -0.8122    1.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2349   -0.1461    0.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3943   -0.2062   -0.1729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0383   -0.4481   -2.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5907    0.4738   -2.1918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8687    2.0833   -3.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2032    2.5486   -0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3440    1.1592    0.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0363    3.6315    0.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1670    4.0445   -0.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0550    2.5643    1.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7869    0.4106    2.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781    0.1659   -1.8272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5916   -0.5517   -2.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6731    0.3515   -3.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8991   -3.1840   -5.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6171   -4.6391   -4.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1916   -3.8322   -4.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1086    0.0989   -0.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9771   -2.9105   -0.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8045   -2.2850   -1.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9715   -0.3193   -0.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0894   -1.1793    0.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3577    1.0360    1.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3175    1.7807    0.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5235    2.1129   -1.1115 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8847    2.4378   -0.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6551    2.6459    1.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7462    0.6364    3.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3307    0.3163    2.7571 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 21 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 38 40  1  0
 40 41  2  0
 28  5  1  0
 41 35  1  0
 19 10  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  6 45  1  0
  8 46  1  1
 10 47  1  1
 12 48  1  1
 13 49  1  0
 13 50  1  0
 14 51  1  0
 15 52  1  6
 16 53  1  0
 17 54  1  1
 18 55  1  0
 19 56  1  1
 20 57  1  0
 22 58  1  0
 23 59  1  0
 23 60  1  0
 26 61  1  0
 26 62  1  0
 26 63  1  0
 28 64  1  6
 29 65  1  0
 29 66  1  0
 33 67  1  0
 33 68  1  0
 34 69  1  0
 34 70  1  0
 36 71  1  0
 37 72  1  0
 39 73  1  0
 40 74  1  0
 41 75  1  0
M  END


  Mrv0541 05061308182D          

 41 43  0  0  0  0            999 V2000
    1.9533   10.5835    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
    0.0000    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.0125    0.0000 C   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    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7035    8.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9066    8.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5367   10.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3336   10.2136    0.0000 O   0  0  0  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    8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   11.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 O   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
    2.3232    9.2032    0.0000 O   0  0  0  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
    5.7158    8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 14  1  1  0  0  0  0
 15  3  2  0  0  0  0
 15  4  1  0  0  0  0
 15  7  1  0  0  0  0
 16  5  2  0  0  0  0
 16  6  1  0  0  0  0
 17  8  2  0  0  0  0
 18 11  1  0  0  0  0
 18 17  1  0  0  0  0
 19 13  2  0  0  0  0
 19 18  1  0  0  0  0
 20 12  1  0  0  0  0
 21 11  1  0  0  0  0
 22 20  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 19  1  0  0  0  0
 26 17  1  0  0  0  0
 27 24  1  0  0  0  0
 28 12  1  0  0  0  0
 29 14  2  0  0  0  0
 30 16  1  0  0  0  0
 31 21  2  0  0  0  0
 32 22  1  0  0  0  0
 33 23  1  0  0  0  0
 34 24  1  0  0  0  0
 35 25  2  0  0  0  0
 36  2  1  0  0  0  0
 36 25  1  0  0  0  0
 37 10  1  0  0  0  0
 37 14  1  0  0  0  0
 38  9  1  0  0  0  0
 38 21  1  0  0  0  0
 39 13  1  0  0  0  0
 39 26  1  0  0  0  0
 40 20  1  0  0  0  0
 40 27  1  0  0  0  0
 41 26  1  0  0  0  0
 41 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217423

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=COC(OC2OC(CO)C(O)C(O)C2O)\C(=C\COC(C)=O)C1CC(=O)OCCC1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O14/c1-14(29)37-10-8-17-18(11-21(31)38-9-7-15-3-5-16(30)6-4-15)19(25(35)36-2)13-39-26(17)41-27-24(34)23(33)22(32)20(12-28)40-27/h3-6,8,13,18,20,22-24,26-28,30,32-34H,7,9-12H2,1-2H3/b17-8+

> <INCHI_KEY>
DKRXODJAISNRGA-CAOOACKPSA-N

> <FORMULA>
C27H34O14

> <MOLECULAR_WEIGHT>
582.5505

> <EXACT_MASS>
582.194855796

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
58.65191145960938

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (3E)-3-[2-(acetyloxy)ethylidene]-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

> <ALOGPS_LOGP>
0.51

> <JCHEM_LOGP>
-0.4248046690000002

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.502885422955552

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.50284178417247

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810849052288777

> <JCHEM_POLAR_SURFACE_AREA>
207.73999999999992

> <JCHEM_REFRACTIVITY>
137.16349999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (5E)-5-[2-(acetyloxy)ethylidene]-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       3.646  19.756   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  C   UNK     0       0.000  15.400   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  13.090   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  16.170   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  13.860   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  13.090   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.913  16.489   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  13.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.426  16.090   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  13.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.671  17.710   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669  13.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.735  18.667   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  13.860   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667  15.400   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  15.400   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  13.860   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336  13.090   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.337  18.480   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  13.860   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.337  20.020   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.003  20.790   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.669  20.020   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336  11.550   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336  16.170   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.669  18.480   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      16.004  18.480   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       6.223  19.065   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -4.001  16.170   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       5.335  15.400   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      14.671  20.790   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      12.003  22.330   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       9.336  20.790   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      10.669  10.780   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       8.002  10.780   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       4.337  17.179   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       4.001  13.090   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      10.669  15.400   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      12.003  17.710   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       9.336  17.710   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   36                                                            
CONECT    3    5   15                                                       
CONECT    4    6   15                                                       
CONECT    5    3   16                                                       
CONECT    6    4   16                                                       
CONECT    7    9   15                                                       
CONECT    8   10   17                                                       
CONECT    9    7   38                                                       
CONECT   10    8   37                                                       
CONECT   11   18   21                                                       
CONECT   12   20   28                                                       
CONECT   13   19   39                                                       
CONECT   14    1   29   37                                                  
CONECT   15    3    4    7                                                  
CONECT   16    5    6   30                                                  
CONECT   17    8   18   26                                                  
CONECT   18   11   17   19                                                  
CONECT   19   13   18   25                                                  
CONECT   20   12   22   40                                                  
CONECT   21   11   31   38                                                  
CONECT   22   20   23   32                                                  
CONECT   23   22   24   33                                                  
CONECT   24   23   27   34                                                  
CONECT   25   19   35   36                                                  
CONECT   26   17   39   41                                                  
CONECT   27   24   40   41                                                  
CONECT   28   12                                                            
CONECT   29   14                                                            
CONECT   30   16                                                            
CONECT   31   21                                                            
CONECT   32   22                                                            
CONECT   33   23                                                            
CONECT   34   24                                                            
CONECT   35   25                                                            
CONECT   36    2   25                                                       
CONECT   37   10   14                                                       
CONECT   38    9   21                                                       
CONECT   39   13   26                                                       
CONECT   40   20   27                                                       
CONECT   41   26   27                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END

View in JSmol

Synonyms

Value	Source
Methyl (3E)-3-[2-(acetyloxy)ethylidene]-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid	Generator

Chemical Formula

C₂₇H₃₄O₁₄

Average Mass

582.5505 Da

Monoisotopic Mass

582.19486 Da

IUPAC Name

methyl (3E)-3-[2-(acetyloxy)ethylidene]-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

Traditional Name

methyl (5E)-5-[2-(acetyloxy)ethylidene]-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=COC(OC2OC(CO)C(O)C(O)C2O)\C(=C\COC(C)=O)C1CC(=O)OCCC1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C27H34O14/c1-14(29)37-10-8-17-18(11-21(31)38-9-7-15-3-5-16(30)6-4-15)19(25(35)36-2)13-39-26(17)41-27-24(34)23(33)22(32)20(12-28)40-27/h3-6,8,13,18,20,22-24,26-28,30,32-34H,7,9-12H2,1-2H3/b17-8+

InChI Key

DKRXODJAISNRGA-CAOOACKPSA-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
Osmanthus fortunei	LOTUS Database	35616633
Osmanthus fragrans	LOTUS Database	35616633
Osmanthus heterophyllus	LOTUS Database	35616633

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
Glycosyl compound
Secoiridoid-skeleton
O-glycosyl compound
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Tyrosol derivative
Tricarboxylic acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Sugar acid
Phenol
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Oxane
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Primary 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	0.51	ALOGPS
logP	-0.42	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	4.5	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	207.74 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	137.16 m³·mol⁻¹	ChemAxon
Polarizability	58.65 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

HMDB0035217

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013865

KNApSAcK ID

C00010787

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

131751686

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (5e)-5-[2-(acetyloxy)ethylidene]-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate (NP0217423)

MOL for NP0217423 (methyl (5e)-5-[2-(acetyloxy)ethylidene]-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D MOL for NP0217423 (methyl (5e)-5-[2-(acetyloxy)ethylidene]-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D SDF for NP0217423 (methyl (5e)-5-[2-(acetyloxy)ethylidene]-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D-SDF for NP0217423 (methyl (5e)-5-[2-(acetyloxy)ethylidene]-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

PDB for NP0217423 (methyl (5e)-5-[2-(acetyloxy)ethylidene]-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D PDB for NP0217423 (methyl (5e)-5-[2-(acetyloxy)ethylidene]-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

SMILES for NP0217423 (methyl (5e)-5-[2-(acetyloxy)ethylidene]-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

INCHI for NP0217423 (methyl (5e)-5-[2-(acetyloxy)ethylidene]-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

Structure for NP0217423 (methyl (5e)-5-[2-(acetyloxy)ethylidene]-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D Structure for NP0217423 (methyl (5e)-5-[2-(acetyloxy)ethylidene]-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)