NP-MRD: Showing NP-Card for methyl (5e,6s)-5-ethylidene-4-{2-oxo-2-[2-(4-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)ethoxy]ethyl}-6-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate (NP0301751)

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Record Information

Version

2.0

Created at

2022-09-10 14:54:23 UTC

Updated at

2022-09-10 14:54:23 UTC

NP-MRD ID

NP0301751

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (5e,6s)-5-ethylidene-4-{2-oxo-2-[2-(4-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)ethoxy]ethyl}-6-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate

Description

Methyl (2S,3E)-3-ethylidene-4-{2-oxo-2-[2-(4-{[(3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)ethoxy]ethyl}-2-{[(3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate 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. methyl (5e,6s)-5-ethylidene-4-{2-oxo-2-[2-(4-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)ethoxy]ethyl}-6-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate is found in Fraxinus angustifolia. Based on a literature review very few articles have been published on methyl (2S,3E)-3-ethylidene-4-{2-oxo-2-[2-(4-{[(3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)ethoxy]ethyl}-2-{[(3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102216542D          

 72 75  0  0  1  0            999 V2000
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  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
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    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   -4.1250    0.0000 C   0  0  0  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   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    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
    5.0013   -5.3625    0.0000 O   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
    5.7158   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    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
    2.8579   -6.6000    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
    2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   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   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1060   -5.4487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  1  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   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 C   0  0  2  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
   -4.2868   -6.6000    0.0000 O   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   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 O   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
   -5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 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
 18 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 29 34  1  0  0  0  0
 16 34  1  0  0  0  0
 34 35  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 14 39  1  0  0  0  0
 39 40  2  0  0  0  0
 11 40  1  0  0  0  0
  4 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 41 46  2  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
  3 48  1  0  0  0  0
 48 49  1  1  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  6  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 55 57  2  0  0  0  0
 52 58  1  0  0  0  0
 58 59  1  1  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 60 62  2  0  0  0  0
 58 63  1  0  0  0  0
 63 64  1  6  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
 65 67  2  0  0  0  0
 63 68  1  0  0  0  0
 50 68  1  0  0  0  0
 68 69  1  1  0  0  0
 69 70  1  0  0  0  0
 70 71  1  0  0  0  0
 70 72  2  0  0  0  0
M  END

     RDKit          3D

130133  0  0  0  0  0  0  0  0999 V2000
   -3.6749   -0.5601    3.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3343   -0.6484    2.3777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7681   -0.0379    1.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4790   -0.1619    0.0307 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3851   -1.1921   -0.0885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6084   -0.6659   -0.4538 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0345   -1.0435   -1.7300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3148   -0.5474   -1.9321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.5750   -0.2155   -3.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4873   -1.3284   -4.2403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2857   -2.4525   -4.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1443   -3.6095   -5.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1761   -2.4977   -3.2887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7087    0.5821   -1.0143 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.0030    1.0393   -1.4552 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2319    2.3511   -1.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5212    2.8811   -2.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2379    3.1309   -1.8022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8293    0.0121    0.3664 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.8269    0.9498    1.4027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8819    1.0625    2.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8847    2.0449    3.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8561    0.3021    2.1196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6970   -1.0061    0.5233 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.1629   -2.3081    0.2283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2564   -3.3267    1.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7595   -4.6939    0.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9046   -3.1184    2.3534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4243   -0.2078   -0.9604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6634    0.9501   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2055    1.4693    0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4247    2.6880    0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1823    3.2073   -0.9889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9130    3.3574    1.2258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1534    4.5674    1.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5061    0.6866    1.4095 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3232   -0.2031    1.6981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1301    0.6533    1.9927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8204    0.8465    1.2079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0538    1.2766    3.2011 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7720    2.0815    3.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1111    1.7024    4.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0631    1.3566    3.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7871    2.3592    2.6633 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7613    2.0915    1.7563 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0539    0.7533    1.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0582    0.5788    0.5313 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6056   -0.6150    0.0707 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5249   -0.6293   -1.3156 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7757   -0.3237   -1.8809 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6245    0.0316   -3.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8547    0.3682   -3.9306 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6444    1.4309   -3.5125 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9312    1.6999   -4.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2764    2.1613   -2.5411 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7552   -1.4279   -1.6179 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9737   -1.1009   -2.2875 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4531   -1.9546   -3.3032 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6974   -1.6755   -4.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7804   -2.9784   -3.5798 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9758   -1.5471   -0.1453 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9774   -2.9095    0.3053 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1241   -3.4815    0.8736 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2021   -4.8684    1.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1284   -2.7533    0.9630 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9979   -0.7228    0.6214 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5222    0.5392    1.0024 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7917    0.9021    2.3064 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3409    2.2223    2.7111 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5507    0.0464    3.1930 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


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M  END
> <DATABASE_ID>
NP0301751

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](OC2O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)\C(=C\C)C1CC(=O)OCCC1=CC=C(OC2O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C47H58O25/c1-11-32-33(34(44(57)58-10)19-62-45(32)72-47-43(68-29(9)55)41(66-27(7)53)39(64-25(5)51)36(71-47)21-61-23(3)49)18-37(56)59-17-16-30-12-14-31(15-13-30)69-46-42(67-28(8)54)40(65-26(6)52)38(63-24(4)50)35(70-46)20-60-22(2)48/h11-15,19,33,35-36,38-43,45-47H,16-18,20-21H2,1-10H3/b32-11+/t33?,35-,36-,38-,39-,40+,41+,42-,43-,45+,46?,47?/m1/s1

> <INCHI_KEY>
OUGTUWTXDAQGIR-KOPVUUSOSA-N

> <FORMULA>
C47H58O25

> <MOLECULAR_WEIGHT>
1022.956

> <EXACT_MASS>
1022.326717368

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
130

> <JCHEM_AVERAGE_POLARIZABILITY>
101.46663595812329

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S,3E)-3-ethylidene-4-{2-oxo-2-[2-(4-{[(3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)ethoxy]ethyl}-2-{[(3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

> <JCHEM_LOGP>
1.6757762666666622

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.887707085009668

> <JCHEM_POLAR_SURFACE_AREA>
309.15

> <JCHEM_REFRACTIVITY>
231.59370000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
30

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (5E,6S)-5-ethylidene-4-{2-oxo-2-[2-(4-{[(3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)ethoxy]ethyl}-6-{[(3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.669 -12.320   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      13.337 -13.860   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.336 -16.170   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.669 -16.940   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.669 -18.480   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.002 -16.940   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+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 -11.550   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       0.198 -10.171   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      -9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      -8.002 -12.320   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      -8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      -9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      -6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0     -10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0     -12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0     -12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0     -10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0     -13.337 -12.320   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0     -10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0     -12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   65  C   UNK     0     -13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0     -13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0     -14.670  -6.930   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   69  O   UNK     0      -9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   70  C   UNK     0     -10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0     -10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   72  O   UNK     0     -12.003  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   48                                                  
CONECT    4    3    5   41                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   40                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   39                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   34                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   18   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   29   16   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   14   40                                                       
CONECT   40   39   11                                                       
CONECT   41    4   42   46                                                  
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44                                                            
CONECT   46   41   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47    3   49                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51   68                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53   58                                                  
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55                                                            
CONECT   58   52   59   63                                                  
CONECT   59   58   60                                                       
CONECT   60   59   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60                                                            
CONECT   63   58   64   68                                                  
CONECT   64   63   65                                                       
CONECT   65   64   66   67                                                  
CONECT   66   65                                                            
CONECT   67   65                                                            
CONECT   68   63   50   69                                                  
CONECT   69   68   70                                                       
CONECT   70   69   71   72                                                  
CONECT   71   70                                                            
CONECT   72   70                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  150    0
END

View in JSmol

Synonyms

Value	Source
Methyl (2S,3E)-3-ethylidene-4-{2-oxo-2-[2-(4-{[(3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)ethoxy]ethyl}-2-{[(3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid	Generator

Chemical Formula

C₄₇H₅₈O₂₅

Average Mass

1022.9560 Da

Monoisotopic Mass

1022.32672 Da

IUPAC Name

methyl (2S,3E)-3-ethylidene-4-{2-oxo-2-[2-(4-{[(3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)ethoxy]ethyl}-2-{[(3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

Traditional Name

methyl (5E,6S)-5-ethylidene-4-{2-oxo-2-[2-(4-{[(3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)ethoxy]ethyl}-6-{[(3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](OC2O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)\C(=C\C)C1CC(=O)OCCC1=CC=C(OC2O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)C=C1

InChI Identifier

InChI=1S/C47H58O25/c1-11-32-33(34(44(57)58-10)19-62-45(32)72-47-43(68-29(9)55)41(66-27(7)53)39(64-25(5)51)36(71-47)21-61-23(3)49)18-37(56)59-17-16-30-12-14-31(15-13-30)69-46-42(67-28(8)54)40(65-26(6)52)38(63-24(4)50)35(70-46)20-60-22(2)48/h11-15,19,33,35-36,38-43,45-47H,16-18,20-21H2,1-10H3/b32-11+/t33?,35-,36-,38-,39-,40+,41+,42-,43-,45+,46?,47?/m1/s1

InChI Key

OUGTUWTXDAQGIR-KOPVUUSOSA-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
Fraxinus angustifolia	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
Phenolic glycoside
O-glycosyl compound
Secoiridoid-skeleton
Glycosyl compound
Tyrosol derivative
Monoterpenoid
Monocyclic monoterpenoid
Aromatic monoterpenoid
Phenoxy compound
Phenol ether
Sugar acid
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	1.68	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	309.15 Å²	ChemAxon
Rotatable Bond Count	30	ChemAxon
Refractivity	231.59 m³·mol⁻¹	ChemAxon
Polarizability	101.47 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

163034140

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,6s)-5-ethylidene-4-{2-oxo-2-[2-(4-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)ethoxy]ethyl}-6-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate (NP0301751)

MOL for NP0301751 (methyl (5e,6s)-5-ethylidene-4-{2-oxo-2-[2-(4-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)ethoxy]ethyl}-6-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D MOL for NP0301751 (methyl (5e,6s)-5-ethylidene-4-{2-oxo-2-[2-(4-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)ethoxy]ethyl}-6-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D SDF for NP0301751 (methyl (5e,6s)-5-ethylidene-4-{2-oxo-2-[2-(4-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)ethoxy]ethyl}-6-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D-SDF for NP0301751 (methyl (5e,6s)-5-ethylidene-4-{2-oxo-2-[2-(4-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)ethoxy]ethyl}-6-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

PDB for NP0301751 (methyl (5e,6s)-5-ethylidene-4-{2-oxo-2-[2-(4-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)ethoxy]ethyl}-6-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D PDB for NP0301751 (methyl (5e,6s)-5-ethylidene-4-{2-oxo-2-[2-(4-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)ethoxy]ethyl}-6-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

SMILES for NP0301751 (methyl (5e,6s)-5-ethylidene-4-{2-oxo-2-[2-(4-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)ethoxy]ethyl}-6-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

INCHI for NP0301751 (methyl (5e,6s)-5-ethylidene-4-{2-oxo-2-[2-(4-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)ethoxy]ethyl}-6-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

Structure for NP0301751 (methyl (5e,6s)-5-ethylidene-4-{2-oxo-2-[2-(4-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)ethoxy]ethyl}-6-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D Structure for NP0301751 (methyl (5e,6s)-5-ethylidene-4-{2-oxo-2-[2-(4-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}phenyl)ethoxy]ethyl}-6-{[(3r,4s,5r,6r)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)