NP-MRD: Showing NP-Card for (2s,3r,4s,5r,6r)-6-[(2r)-3-{[(2e)-3-(4-{[(1r,2s)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3-methoxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid (NP0291644)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-09 22:48:45 UTC

Updated at

2022-09-09 22:48:45 UTC

NP-MRD ID

NP0291644

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5r,6r)-6-[(2r)-3-{[(2e)-3-(4-{[(1r,2s)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3-methoxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

Description

(2S,3R,4S,5R,6R)-6-[(2R)-3-{[(2E)-3-(4-{[(1R,2S)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3-methoxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones. (2s,3r,4s,5r,6r)-6-[(2r)-3-{[(2e)-3-(4-{[(1r,2s)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3-methoxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid is found in Medicago truncatula. Based on a literature review very few articles have been published on (2S,3R,4S,5R,6R)-6-[(2R)-3-{[(2E)-3-(4-{[(1R,2S)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3-methoxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102200482D          

 45 47  0  0  1  0            999 V2000
   -6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    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
    1.4289   -4.1250    0.0000 C   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
    2.1434   -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
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    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
    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
    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  2  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  2  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
    5.7158   -4.9500    0.0000 C   0  0  1  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
   -0.7145   -2.8875    0.0000 C   0  0  0  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
   -2.1434   -2.8875    0.0000 O   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   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 C   0  0  0  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
  1  2  1  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  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 28 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 26 36  1  0  0  0  0
 36 37  1  1  0  0  0
 15 38  1  0  0  0  0
 38 39  2  0  0  0  0
 12 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
  5 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
  3 44  1  0  0  0  0
 44 45  1  0  0  0  0
M  END

     RDKit          3D

 81 83  0  0  0  0  0  0  0  0999 V2000
  -11.6054   -1.6607    1.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6287   -0.6527    0.3263 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4468    0.0334    0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2755   -0.2360    0.7665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0880    0.4221    0.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8547    0.0924    1.2922 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1331   -0.2823    2.5831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9428   -0.8870    0.5467 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5656   -2.2842    0.5794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7293   -2.3827   -0.1401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7781   -0.9488    1.2675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4956   -0.6415    1.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6034   -0.8833    2.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2638   -0.5964    2.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7336   -0.0565    0.8372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6901    0.2396    0.7304 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2800    0.7488   -0.3299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7097    1.0250   -0.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1863    1.5118   -1.4357 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5529    0.7678    0.6904 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9711    1.0957    0.4973 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6240    0.7255    1.7728 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9672    1.4546    2.8379 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0783    0.9949    1.9506 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9509    0.4348    1.1138 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9768    0.8259   -0.1694 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7284   -0.2530   -1.0053 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7998   -0.7149   -1.7157 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4329   -2.0686   -2.2446 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3163   -2.6036   -2.0247 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3443   -2.7863   -3.0133 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9585   -0.9352   -0.7433 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4770   -1.5832    0.3757 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4469    0.4773   -0.4046 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9969    0.5080    0.8735 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3279    1.4727   -0.5273 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2098    2.0549   -1.7698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6185    0.1724   -0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9882   -0.1127   -0.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8430    0.1322   -1.1397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3682    0.6863   -2.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0899    1.4130   -0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2374    1.7064   -1.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4108    1.0238   -0.8776 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5676    1.3355   -1.6002 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3077   -1.1932    2.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7707   -2.3587    1.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5481   -2.2219    1.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3207   -1.0013    1.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2644    1.0724    1.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3645   -0.7726    2.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9048   -0.4978   -0.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8391   -3.0017    0.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7048   -2.6150    1.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5979   -2.3536   -1.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0097   -1.3046    3.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5838   -0.7875    2.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3601    0.0365    1.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6766    0.9701   -1.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2644    0.5297   -0.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0481    2.1721    0.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4401   -0.3396    2.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0657    2.4133    2.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2924    0.6566    3.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2642    2.1261    2.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2434    1.6185   -0.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0920   -0.1233   -2.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0295   -3.1121   -3.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7243   -1.5149   -1.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7926   -2.2599    0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2103    0.7266   -1.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5914   -0.2433    1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4882    2.2651    0.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7098    2.9121   -1.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2941    0.5877   -1.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1808    0.7369   -3.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8572    1.6563   -2.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5597   -0.0279   -2.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1631    1.9265   -0.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2411    2.4871   -1.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5391    2.0500   -2.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 42  2  0
 42 43  1  0
 43 44  2  0
 44 45  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
 28 29  1  0
 29 31  1  0
 29 30  2  0
 15 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  1  0
 44  3  1  0
 39 12  1  0
 36 26  1  0
  1 46  1  0
  1 47  1  0
  1 48  1  0
  4 49  1  0
 42 79  1  0
 43 80  1  0
 45 81  1  0
  6 50  1  1
  7 51  1  0
  8 52  1  6
  9 53  1  0
  9 54  1  0
 10 55  1  0
 13 56  1  0
 14 57  1  0
 16 58  1  0
 17 59  1  0
 21 60  1  0
 21 61  1  0
 22 62  1  1
 23 63  1  0
 24 64  1  0
 24 65  1  0
 26 66  1  1
 28 67  1  6
 32 69  1  6
 33 70  1  0
 34 71  1  6
 35 72  1  0
 36 73  1  1
 37 74  1  0
 31 68  1  0
 38 75  1  0
 41 76  1  0
 41 77  1  0
 41 78  1  0
M  END


  Mrv1652309102200482D          

 45 47  0  0  1  0            999 V2000
   -6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    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
    1.4289   -4.1250    0.0000 C   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
    2.1434   -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
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    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
    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
    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  2  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  2  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
    5.7158   -4.9500    0.0000 C   0  0  1  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
   -0.7145   -2.8875    0.0000 C   0  0  0  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
   -2.1434   -2.8875    0.0000 O   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   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 C   0  0  0  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
  1  2  1  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  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 28 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 26 36  1  0  0  0  0
 36 37  1  1  0  0  0
 15 38  1  0  0  0  0
 38 39  2  0  0  0  0
 12 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
  5 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
  3 44  1  0  0  0  0
 44 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0291644

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)[C@@H](O)[C@H](CO)OC1=CC=C(\C=C\C(=O)OC[C@H](O)CO[C@@H]2O[C@@H]([C@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O16/c1-40-19-10-15(5-6-17(19)32)23(34)21(11-30)44-18-7-3-14(9-20(18)41-2)4-8-22(33)42-12-16(31)13-43-29-26(37)24(35)25(36)27(45-29)28(38)39/h3-10,16,21,23-27,29-32,34-37H,11-13H2,1-2H3,(H,38,39)/b8-4+/t16-,21-,23+,24-,25+,26+,27-,29+/m0/s1

> <INCHI_KEY>
KAPAGFZZBVGHML-LBUUIVEHSA-N

> <FORMULA>
C29H36O16

> <MOLECULAR_WEIGHT>
640.591

> <EXACT_MASS>
640.200335079

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
63.79373123300708

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6R)-6-[(2R)-3-{[(2E)-3-(4-{[(1R,2S)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3-methoxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

> <JCHEM_LOGP>
-0.5684602976666655

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.906559391396604

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2921134583696388

> <JCHEM_PKA_STRONGEST_BASIC>
-3.389639884574607

> <JCHEM_POLAR_SURFACE_AREA>
251.35999999999996

> <JCHEM_REFRACTIVITY>
150.27259999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6R)-6-[(2R)-3-{[(2E)-3-(4-{[(1R,2S)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3-methoxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

> <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     -12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0     -10.669  -0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      14.670  -5.390   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      16.004  -7.700   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      14.670 -10.010   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0     -10.669  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   44                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   42                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   39                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   38                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   36                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   28   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   26   37                                                  
CONECT   37   36                                                            
CONECT   38   15   39                                                       
CONECT   39   38   12   40                                                  
CONECT   40   39   41                                                       
CONECT   41   40                                                            
CONECT   42    5   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43    3   45                                                  
CONECT   45   44                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   94    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4S,5R,6R)-6-[(2R)-3-{[(2E)-3-(4-{[(1R,2S)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3-methoxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylate	Generator

Chemical Formula

C₂₉H₃₆O₁₆

Average Mass

640.5910 Da

Monoisotopic Mass

640.20034 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)[C@@H](O)[C@H](CO)OC1=CC=C(\C=C\C(=O)OC[C@H](O)CO[C@@H]2O[C@@H]([C@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C1OC

InChI Identifier

InChI=1S/C29H36O16/c1-40-19-10-15(5-6-17(19)32)23(34)21(11-30)44-18-7-3-14(9-20(18)41-2)4-8-22(33)42-12-16(31)13-43-29-26(37)24(35)25(36)27(45-29)28(38)39/h3-10,16,21,23-27,29-32,34-37H,11-13H2,1-2H3,(H,38,39)/b8-4+/t16-,21-,23+,24-,25+,26+,27-,29+/m0/s1

InChI Key

KAPAGFZZBVGHML-LBUUIVEHSA-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
Medicago truncatula	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan glycosides

Sub Class

Not Available

Direct Parent

Lignan glycosides

Alternative Parents

Substituents

Lignan glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hexose monosaccharide
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Methoxyphenol
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
Styrene
Glycerolipid
Fatty acid ester
Beta-hydroxy acid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Oxane
Monocyclic benzene moiety
Fatty acyl
Dicarboxylic acid or derivatives
Monosaccharide
Benzenoid
Hydroxy acid
Pyran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Oxacycle
Carboxylic acid
Acetal
Ether
Primary alcohol
Carbonyl group
Aromatic alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Alcohol
Organic oxygen 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	-0.57	ChemAxon
pKa (Strongest Acidic)	3.29	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	251.36 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	150.27 m³·mol⁻¹	ChemAxon
Polarizability	63.79 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163188221

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5r,6r)-6-[(2r)-3-{[(2e)-3-(4-{[(1r,2s)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3-methoxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid (NP0291644)

MOL for NP0291644 ((2s,3r,4s,5r,6r)-6-[(2r)-3-{[(2e)-3-(4-{[(1r,2s)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3-methoxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D MOL for NP0291644 ((2s,3r,4s,5r,6r)-6-[(2r)-3-{[(2e)-3-(4-{[(1r,2s)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3-methoxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D SDF for NP0291644 ((2s,3r,4s,5r,6r)-6-[(2r)-3-{[(2e)-3-(4-{[(1r,2s)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3-methoxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D-SDF for NP0291644 ((2s,3r,4s,5r,6r)-6-[(2r)-3-{[(2e)-3-(4-{[(1r,2s)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3-methoxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

PDB for NP0291644 ((2s,3r,4s,5r,6r)-6-[(2r)-3-{[(2e)-3-(4-{[(1r,2s)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3-methoxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D PDB for NP0291644 ((2s,3r,4s,5r,6r)-6-[(2r)-3-{[(2e)-3-(4-{[(1r,2s)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3-methoxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

SMILES for NP0291644 ((2s,3r,4s,5r,6r)-6-[(2r)-3-{[(2e)-3-(4-{[(1r,2s)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3-methoxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

INCHI for NP0291644 ((2s,3r,4s,5r,6r)-6-[(2r)-3-{[(2e)-3-(4-{[(1r,2s)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3-methoxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

Structure for NP0291644 ((2s,3r,4s,5r,6r)-6-[(2r)-3-{[(2e)-3-(4-{[(1r,2s)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3-methoxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D Structure for NP0291644 ((2s,3r,4s,5r,6r)-6-[(2r)-3-{[(2e)-3-(4-{[(1r,2s)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3-methoxyphenyl)prop-2-enoyl]oxy}-2-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid)