NP-MRD: Showing NP-Card for (2e)-3-({[(2r,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-4-hydroxybut-2-en-1-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0165354)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 00:28:06 UTC

Updated at

2022-09-03 00:28:06 UTC

NP-MRD ID

NP0165354

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-3-({[(2r,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-4-hydroxybut-2-en-1-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Description

Aohadaglycoside C belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. (2e)-3-({[(2r,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-4-hydroxybut-2-en-1-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate is found in Ilex macropoda. Based on a literature review very few articles have been published on Aohadaglycoside C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032202282D          

 43 45  0  0  1  0            999 V2000
    0.7145   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    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
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  2  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
   -5.0013   -6.1875    0.0000 C   0  0  2  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
   -6.4302   -6.1875    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
   -7.1447   -7.4250    0.0000 O   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
   -8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  1  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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 30 37  1  0  0  0  0
 23 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 40 41  1  6  0  0  0
 40 42  1  0  0  0  0
 21 42  1  0  0  0  0
 42 43  1  1  0  0  0
M  END

     RDKit          3D

 75 77  0  0  0  0  0  0  0  0999 V2000
   -5.3021   -0.2993   -1.5184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7972    0.7325   -0.9737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2426    0.7862   -0.6787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0392   -0.2211   -0.9707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4649   -0.2570   -0.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1924   -1.3801   -1.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5478   -1.4264   -0.8426 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2152   -0.3508   -0.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5784   -0.4146   -0.0123 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5055    0.7644    0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1298    1.8572    0.7176 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1433    0.7771   -0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9473    1.7689   -0.6796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5434    1.7048   -0.9712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8958    0.5919   -0.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2538   -0.4346   -0.7970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1178   -0.5683   -2.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8012   -0.5897   -2.7154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6860   -1.4859    0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3402   -1.6743    0.0154 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4406   -0.5784    0.3834 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3309   -0.2925   -0.5718 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5998    0.1547   -0.2293 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5840   -0.8311   -0.7569 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9176   -0.6778   -0.4863 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5545   -0.9380    0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9765   -1.3862    1.7090 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0165   -0.6863    0.8220 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7003   -0.2155   -0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1191    0.0626   -0.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7348    0.5622   -1.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0838    0.8400   -1.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8603    0.6229   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2077    0.8930   -0.2314 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2627    0.1281    0.9116 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0277   -0.0899    2.0281 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8938   -0.1457    0.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7707    0.7636    1.0822 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3622    2.1476    1.0327 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9700    0.1244    2.1843 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6814   -0.2306    3.3059 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1548   -1.0376    1.6615 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1818   -1.4080    2.5944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6397    1.6556   -0.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5428   -1.0879   -1.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7339   -2.2478   -1.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1365   -2.2901   -1.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1273    0.3060    0.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0929    1.9375    0.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6098    1.6692    0.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1442    2.6606   -0.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3538    1.8359   -2.0266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9368    0.5895    0.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6482   -1.5075   -2.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6094    0.2576   -2.7903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7868   -0.3255   -3.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2152   -2.4734   -0.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9197   -1.2717    1.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1869    0.2995    0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7156    1.0657   -0.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5095   -0.8679   -1.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2441   -1.9036   -0.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5370   -0.8848    1.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1328   -0.0260   -1.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1679    0.7483   -2.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5698    1.2322   -2.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.7788    0.7393    0.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5909   -0.4557    2.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5090   -0.5302    1.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8159    0.8430    1.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3685    2.4671    1.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2115    0.8746    2.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8805    0.5144    3.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8212   -1.8703    1.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1432   -2.3832    2.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 16  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35 37  2  0
 23 38  1  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 40 42  1  0
 42 43  1  0
 16 15  2  0
 15 14  1  0
 14 13  1  0
 13  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 42 21  1  0
 12  5  1  0
 37 30  1  0
 18 56  1  0
 17 54  1  0
 17 55  1  0
 19 57  1  0
 19 58  1  0
 21 59  1  1
 23 60  1  6
 24 61  1  0
 24 62  1  0
 28 63  1  0
 29 64  1  0
 31 65  1  0
 32 66  1  0
 34 67  1  0
 36 68  1  0
 37 69  1  0
 38 70  1  1
 39 71  1  0
 40 72  1  1
 41 73  1  0
 42 74  1  6
 43 75  1  0
 15 53  1  0
 14 51  1  0
 14 52  1  0
  3 44  1  0
  4 45  1  0
  6 46  1  0
  7 47  1  0
  9 48  1  0
 11 49  1  0
 12 50  1  0
M  END


  Mrv1652309032202282D          

 43 45  0  0  1  0            999 V2000
    0.7145   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -12.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    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
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  2  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
   -5.0013   -6.1875    0.0000 C   0  0  2  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
   -6.4302   -6.1875    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
   -7.1447   -7.4250    0.0000 O   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
   -8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  1  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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 30 37  1  0  0  0  0
 23 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 40 41  1  6  0  0  0
 40 42  1  0  0  0  0
 21 42  1  0  0  0  0
 42 43  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0165354

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC\C(CO[C@@H]1O[C@H](COC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@@H](O)[C@H](O)[C@H]1O)=C/COC(=O)\C=C\C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H32O14/c30-13-18(9-10-40-24(35)7-3-16-1-5-19(31)21(33)11-16)14-42-29-28(39)27(38)26(37)23(43-29)15-41-25(36)8-4-17-2-6-20(32)22(34)12-17/h1-9,11-12,23,26-34,37-39H,10,13-15H2/b7-3+,8-4+,18-9+/t23-,26-,27+,28-,29-/m1/s1

> <INCHI_KEY>
ZUFZNUCFZXYFHP-SPSYIVBOSA-N

> <FORMULA>
C29H32O14

> <MOLECULAR_WEIGHT>
604.561

> <EXACT_MASS>
604.17920571

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
60.45942718793145

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-({[(2R,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-4-hydroxybut-2-en-1-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
1.51

> <JCHEM_LOGP>
1.3638112113333334

> <ALOGPS_LOGS>
-3.60

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.50866870425592

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.907381337431033

> <JCHEM_PKA_STRONGEST_BASIC>
-2.76199486906234

> <JCHEM_POLAR_SURFACE_AREA>
232.89999999999998

> <JCHEM_REFRACTIVITY>
150.4012

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-({[(2R,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-4-hydroxybut-2-en-1-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  O   UNK     0       1.334 -16.170   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000 -16.940   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000 -18.480   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334 -19.250   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334 -20.790   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667 -21.560   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667 -23.100   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334 -23.870   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334 -25.410   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000 -23.100   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334 -23.870   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000 -21.560   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334 -16.170   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -8.002 -12.320   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0     -12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0     -13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0     -13.337 -13.860   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0     -14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -18.672 -12.320   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -20.005 -11.550   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -20.005 -10.010   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0     -21.339  -9.240   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0     -18.672  -9.240   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0     -18.672  -7.700   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0     -17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0     -10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5                                                       
CONECT   13    2   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   42                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   38                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   37                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   30                                                       
CONECT   38   23   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   21   43                                                  
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₂O₁₄

Average Mass

604.5610 Da

Monoisotopic Mass

604.17921 Da

IUPAC Name

(2E)-3-({[(2R,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-4-hydroxybut-2-en-1-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

(2E)-3-({[(2R,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-4-hydroxybut-2-en-1-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

OC\C(CO[C@@H]1O[C@H](COC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@@H](O)[C@H](O)[C@H]1O)=C/COC(=O)\C=C\C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C29H32O14/c30-13-18(9-10-40-24(35)7-3-16-1-5-19(31)21(33)11-16)14-42-29-28(39)27(38)26(37)23(43-29)15-41-25(36)8-4-17-2-6-20(32)22(34)12-17/h1-9,11-12,23,26-34,37-39H,10,13-15H2/b7-3+,8-4+,18-9+/t23-,26-,27+,28-,29-/m1/s1

InChI Key

ZUFZNUCFZXYFHP-SPSYIVBOSA-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
Ilex macropoda	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Coumaric acid or derivatives
Cinnamic acid or derivatives
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Styrene
Catechol
Fatty acid ester
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Oxane
Benzenoid
Dicarboxylic acid or derivatives
Monosaccharide
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Primary alcohol
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.51	ALOGPS
logP	1.36	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.91	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	232.9 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	150.4 m³·mol⁻¹	ChemAxon
Polarizability	60.46 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8945260

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10769945

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e)-3-({[(2r,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-4-hydroxybut-2-en-1-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0165354)

MOL for NP0165354 ((2e)-3-({[(2r,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-4-hydroxybut-2-en-1-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D MOL for NP0165354 ((2e)-3-({[(2r,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-4-hydroxybut-2-en-1-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D SDF for NP0165354 ((2e)-3-({[(2r,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-4-hydroxybut-2-en-1-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D-SDF for NP0165354 ((2e)-3-({[(2r,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-4-hydroxybut-2-en-1-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

PDB for NP0165354 ((2e)-3-({[(2r,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-4-hydroxybut-2-en-1-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D PDB for NP0165354 ((2e)-3-({[(2r,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-4-hydroxybut-2-en-1-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

SMILES for NP0165354 ((2e)-3-({[(2r,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-4-hydroxybut-2-en-1-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

INCHI for NP0165354 ((2e)-3-({[(2r,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-4-hydroxybut-2-en-1-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

Structure for NP0165354 ((2e)-3-({[(2r,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-4-hydroxybut-2-en-1-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D Structure for NP0165354 ((2e)-3-({[(2r,3r,4s,5s,6r)-6-({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-4-hydroxybut-2-en-1-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate)