NP-MRD: Showing NP-Card for methyl (4s,5e)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate (NP0219657)

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Record Information

Version

2.0

Created at

2022-09-05 20:43:37 UTC

Updated at

2022-09-05 20:43:38 UTC

NP-MRD ID

NP0219657

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

EXCELSIDE A 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 (4s,5e)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate is found in Fraxinus excelsior. Based on a literature review very few articles have been published on EXCELSIDE A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052222432D          

 40 42  0  0  1  0            999 V2000
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    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
   -5.7158   -4.9500    0.0000 C   0  0  0  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  2  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
   -5.0013   -7.8375    0.0000 C   0  0  0  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
   -6.4302   -7.8375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4302   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.8592   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8592   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1447   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7158   -1.6500    0.0000 O   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
   -2.8579   -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
   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   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
   -2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7645   -0.8963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   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
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  1  0  0  0
  8 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  1  0  0  0
  4 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 30 35  1  0  0  0  0
  3 35  1  0  0  0  0
 35 36  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END

     RDKit          3D

 76 78  0  0  0  0  0  0  0  0999 V2000
    4.4016    3.1815    0.6257 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4022    2.1751    0.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5478    0.8871    0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7899    0.1744    0.6103 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7864    0.7993    1.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9108   -0.1882    1.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9394    0.1889    2.3329 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7990   -1.4992    1.3399 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8869   -2.3826    1.6242 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2936   -0.2443   -0.7416 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5692   -0.0582   -1.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7891   -0.4805   -2.4863 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6654    0.5561   -0.7168 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9148    0.7122   -1.3413 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3365   -0.8465   -1.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6427   -0.4871   -0.8578 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2320   -0.7085   -0.6808 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.1784   -1.2442    0.1816 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.3049   -1.6822    0.8473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9565   -2.0535   -1.0816 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3855   -3.2590   -0.7531 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.9200   -0.6400   -3.0272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0698   -0.5958    1.0791 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4318   -1.5803    1.8029 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8144    1.6512    1.5200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5992    1.3387    0.6069 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1235    2.2052    1.3910 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8565    4.1850    0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2240    3.3270   -0.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7506    3.1843    1.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3853    2.5161   -0.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5175   -0.8227    1.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3648    1.0211    2.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3340    1.6576    1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8185   -1.8221    1.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6542   -3.0370    2.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.7457    0.7140   -0.5837 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1009   -0.0564   -2.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9598    1.7366   -1.8087 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.0094   -1.9270    0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
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  8  6  1  0
  6  7  2  0
  6  5  1  0
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  2  1  1  0
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 10  4  1  0
 39 19  1  0
 33 24  1  0
  9 48  1  0
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  5 46  1  0
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 37 73  1  1
 38 74  1  0
 39 75  1  6
 40 76  1  0
 15 54  1  0
 14 51  1  0
 14 52  1  0
 14 53  1  0
M  END


  Mrv1652309052222432D          

 40 42  0  0  1  0            999 V2000
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    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
   -5.7158   -4.9500    0.0000 C   0  0  0  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  2  0  0  0  0  0  0  0  0  0
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   -5.7158   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -5.0013   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.1447   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.7158   -1.6500    0.0000 O   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
   -2.8579   -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
   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   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
   -2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7645   -0.8963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   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
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  1  0  0  0
  8 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  1  0  0  0
  4 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 30 35  1  0  0  0  0
  3 35  1  0  0  0  0
 35 36  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219657

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H]1\C(=C/C)C(O[C@@H]2O[C@H](CO[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O)OC=C1C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C24H36O16/c1-4-9-10(5-14(26)34-2)11(21(33)35-3)7-36-22(9)40-24-20(32)18(30)16(28)13(39-24)8-37-23-19(31)17(29)15(27)12(6-25)38-23/h4,7,10,12-13,15-20,22-25,27-32H,5-6,8H2,1-3H3/b9-4+/t10-,12+,13+,15+,16+,17-,18-,19+,20+,22?,23+,24-/m0/s1

> <INCHI_KEY>
KIYJRYWOZVDCRC-GLYOJDOWSA-N

> <FORMULA>
C24H36O16

> <MOLECULAR_WEIGHT>
580.536

> <EXACT_MASS>
580.200335079

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
56.07540269329637

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-3.065563568999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.431007251910895

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.908555303714909

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083422322401

> <JCHEM_POLAR_SURFACE_AREA>
240.35999999999996

> <JCHEM_REFRACTIVITY>
127.30209999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -8.002  -4.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -9.336  -6.930   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0     -10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0     -12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0     -12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0     -10.669 -12.320   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0     -10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -9.336 -16.170   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0     -12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -12.003 -16.170   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0     -13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0     -14.670 -14.630   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0     -13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0     -14.670 -11.550   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0     -12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0     -13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0     -12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0     -13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0     -10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0     -10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -3.294  -1.673   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5   28                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   26                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   11   21                                                  
CONECT   21   20                                                            
CONECT   22    8   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    6   27                                                  
CONECT   27   26                                                            
CONECT   28    4   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33                                                            
CONECT   35   30    3   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   84    0
END

View in JSmol

Synonyms

Value	Source
(2S,4S,3E)-Methyl-3-ethylidene-4-(2-methoxy-2-oxoethyl)-2-((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)-3,4-dihydro-2H-pyran-5-carboxylate	MeSH

Chemical Formula

C₂₄H₃₆O₁₆

Average Mass

580.5360 Da

Monoisotopic Mass

580.20034 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@H]1\C(=C/C)C(O[C@@H]2O[C@H](CO[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O)OC=C1C(=O)OC

InChI Identifier

InChI=1S/C24H36O16/c1-4-9-10(5-14(26)34-2)11(21(33)35-3)7-36-22(9)40-24-20(32)18(30)16(28)13(39-24)8-37-23-19(31)17(29)15(27)12(6-25)38-23/h4,7,10,12-13,15-20,22-25,27-32H,5-6,8H2,1-3H3/b9-4+/t10-,12+,13+,15+,16+,17-,18-,19+,20+,22?,23+,24-/m0/s1

InChI Key

KIYJRYWOZVDCRC-GLYOJDOWSA-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 excelsior	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
Disaccharide
Glycosyl compound
Secoiridoid-skeleton
O-glycosyl compound
Monocyclic monoterpenoid
Monoterpenoid
Dicarboxylic acid or derivatives
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Vinylogous ester
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Acetal
Primary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-3.1	ChemAxon
pKa (Strongest Acidic)	11.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	240.36 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	127.3 m³·mol⁻¹	ChemAxon
Polarizability	56.08 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

C00047872

Chemspider ID

24674908

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46881041

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (4s,5e)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate (NP0219657)

MOL for NP0219657 (methyl (4s,5e)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D MOL for NP0219657 (methyl (4s,5e)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D SDF for NP0219657 (methyl (4s,5e)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D-SDF for NP0219657 (methyl (4s,5e)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

PDB for NP0219657 (methyl (4s,5e)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D PDB for NP0219657 (methyl (4s,5e)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

SMILES for NP0219657 (methyl (4s,5e)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

INCHI for NP0219657 (methyl (4s,5e)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

Structure for NP0219657 (methyl (4s,5e)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)

3D Structure for NP0219657 (methyl (4s,5e)-5-ethylidene-4-(2-methoxy-2-oxoethyl)-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylate)