NP-MRD: Showing NP-Card for (2r,3r,4s,5s,6r)-2-{[(3s,5s,6e,10r,11r,14e,16s,18s)-3,18-dihydroxy-3,7,14,18-tetramethyl-10,11-bis(prop-1-en-2-yl)-16-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icosa-1,6,14,19-tetraen-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0260155)

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Record Information

Version

2.0

Created at

2022-09-08 02:13:48 UTC

Updated at

2022-09-08 02:13:48 UTC

NP-MRD ID

NP0260155

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4s,5s,6r)-2-{[(3s,5s,6e,10r,11r,14e,16s,18s)-3,18-dihydroxy-3,7,14,18-tetramethyl-10,11-bis(prop-1-en-2-yl)-16-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icosa-1,6,14,19-tetraen-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

Amarantholidoside VI 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. (2r,3r,4s,5s,6r)-2-{[(3s,5s,6e,10r,11r,14e,16s,18s)-3,18-dihydroxy-3,7,14,18-tetramethyl-10,11-bis(prop-1-en-2-yl)-16-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icosa-1,6,14,19-tetraen-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Amaranthus retroflexus. Based on a literature review very few articles have been published on Amarantholidoside VI.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082204132D          

 56 57  0  0  1  0            999 V2000
   -0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8414   -7.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164   -5.8855    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
   -2.1434   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  1  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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1283   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033   -1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    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
    7.1447   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -6.1875    0.0000 C   0  0  1  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
   -5.0013   -5.3625    0.0000 C   0  0  2  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  1  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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  1  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  1  0  0  0
 25 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 30  1  6  0  0  0
 31 30  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 31 40  1  0  0  0  0
 40 41  1  6  0  0  0
 17 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
  7 45  1  6  0  0  0
 46 45  1  6  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  6  0  0  0
 49 50  1  0  0  0  0
 48 51  1  0  0  0  0
 51 52  1  1  0  0  0
 51 53  1  0  0  0  0
 53 54  1  6  0  0  0
 53 55  1  0  0  0  0
 46 55  1  0  0  0  0
 55 56  1  1  0  0  0
M  END

     RDKit          3D

126127  0  0  0  0  0  0  0  0999 V2000
   -7.6497    3.2491    0.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3416    3.0481    0.7068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7201    2.1683    1.6969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8343    3.0432    2.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7426    1.7207    2.5696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9237    1.0416    1.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6529    0.1004    0.2395 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6803   -0.9336   -0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8375   -0.8308   -1.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9711    0.3746   -2.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9218   -1.9337   -1.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4814   -1.8516   -1.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5701   -0.9586   -2.2022 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7876    0.4506   -1.8477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0127    1.3206   -2.8960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8505    1.0634   -0.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8961   -1.4321   -1.9454 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2486   -1.4277   -0.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5408   -1.7785    0.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7449   -0.9893   -0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3621   -0.8157   -1.5319 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3474   -0.4101    0.8305 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5525    0.4023    0.7288 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2192    1.7542    0.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3656    2.6987    0.0376 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7477    4.0103   -0.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1508    2.2538   -1.0567 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1643    2.9551    1.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6012    3.0654    2.4258 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6494   -0.1528    0.1518 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7618   -0.3148    0.9622 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8940    0.3154    0.5134 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8520    0.4541    1.5165 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.2065    0.7894    0.9785 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2204    1.9829    0.2615 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9221   -0.7969    2.3710 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2623   -0.6347    3.5854 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4075   -2.0014    1.6135 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.2167   -2.3348    0.5457 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9687   -1.8084    1.2384 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1989   -2.1219    2.3575 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1671   -2.6029   -2.7975 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1971   -3.2163   -3.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5412   -3.1712   -3.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6316   -0.6350    0.9707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8837   -0.5660    0.3674 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.8056   -0.2014    1.3436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9781    0.2047    0.7337 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.9209    0.7498    1.7848 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1183    1.1714    1.2121 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5984   -0.9348   -0.0438 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.8173   -0.5670   -1.3660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7832   -2.2004    0.0716 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.1231   -2.8441    1.2602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3164   -1.9770   -0.0700 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8455   -2.2653   -1.3331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2750    2.7210    1.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.7124    3.5855   -0.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3268    4.0009    2.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5367    2.4961    3.5117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9077    3.2121    2.0063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2753    1.3817    3.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0078    1.4551    0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5347    0.4643    2.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1483    0.5657   -0.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6043   -1.8887    0.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0874    0.4944   -2.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6062    1.2998   -1.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5817    0.2054   -3.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2642   -2.2478   -2.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3041   -2.8787   -0.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0816   -2.8966   -1.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3348   -1.4714   -0.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6899   -1.0435   -3.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2127    2.3468   -2.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9892    0.9750   -3.9079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6375    1.8867   -0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0798    1.6234   -0.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1094    0.4214    0.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4467   -0.5603   -2.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9790   -0.4305   -0.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7390   -1.8466   -1.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3147   -0.2292   -1.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9155   -0.5440    1.8423 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9133    0.6164    1.8223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5499    2.2470    0.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6127    1.8013   -0.7044 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3110    3.7794   -1.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9461    4.2704    0.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5153    4.7795   -0.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7847    2.5584   -1.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
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 43112  1  0
M  END


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  6  7  1  0  0  0  0
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 25 27  1  1  0  0  0
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 46 55  1  0  0  0  0
 55 56  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0260155

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@H](CC\C(C)=C\[C@H](C[C@](C)(O)C=C)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@@H](CC\C(C)=C\[C@H](C[C@](C)(O)C=C)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C42H70O14/c1-11-41(9,51)19-27(53-39-37(49)35(47)33(45)31(21-43)55-39)17-25(7)13-15-29(23(3)4)30(24(5)6)16-14-26(8)18-28(20-42(10,52)12-2)54-40-38(50)36(48)34(46)32(22-44)56-40/h11-12,17-18,27-40,43-52H,1-3,5,13-16,19-22H2,4,6-10H3/b25-17+,26-18+/t27-,28-,29+,30+,31-,32-,33-,34-,35+,36+,37-,38-,39-,40-,41-,42-/m1/s1

> <INCHI_KEY>
IAXMSBCBRWSXIH-AGKBTZFZSA-N

> <FORMULA>
C42H70O14

> <MOLECULAR_WEIGHT>
799.008

> <EXACT_MASS>
798.476556934

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
126

> <JCHEM_AVERAGE_POLARIZABILITY>
87.35857049194266

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(3S,5S,6E,10R,11R,14E,16S,18S)-3,18-dihydroxy-3,7,14,18-tetramethyl-10,11-bis(prop-1-en-2-yl)-16-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icosa-1,6,14,19-tetraen-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
1.8025743186666654

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.430240108643549

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.909077150310322

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810836832552097

> <JCHEM_POLAR_SURFACE_AREA>
239.21999999999994

> <JCHEM_REFRACTIVITY>
211.73680000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
23

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(3S,5S,6E,10R,11R,14E,16S,18S)-3,18-dihydroxy-3,7,14,18-tetramethyl-10,11-bis(prop-1-en-2-yl)-16-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icosa-1,6,14,19-tetraen-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334 -13.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.437 -13.654   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.897 -10.986   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.439  -5.954   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.003  -3.850   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.899  -3.286   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.669  -1.953   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.002 -13.860   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      10.669 -13.860   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      13.337 -12.320   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -9.336 -14.630   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      -9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0     -10.669 -12.320   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      -9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0     -10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      -8.002  -7.700   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8   45                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18   42                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29                                                       
CONECT   29   28                                                            
CONECT   30   23   31                                                       
CONECT   31   30   32   40                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   31   41                                                  
CONECT   41   40                                                            
CONECT   42   17   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42                                                            
CONECT   45    7   46                                                       
CONECT   46   45   47   55                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   51                                                  
CONECT   49   48   50                                                       
CONECT   50   49                                                            
CONECT   51   48   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   46   56                                                  
CONECT   56   55                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  114    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₂H₇₀O₁₄

Average Mass

799.0080 Da

Monoisotopic Mass

798.47656 Da

IUPAC Name

(2R,3R,4S,5S,6R)-2-{[(3S,5S,6E,10R,11R,14E,16S,18S)-3,18-dihydroxy-3,7,14,18-tetramethyl-10,11-bis(prop-1-en-2-yl)-16-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icosa-1,6,14,19-tetraen-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=C)[C@H](CC\C(C)=C\[C@H](C[C@](C)(O)C=C)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@@H](CC\C(C)=C\[C@H](C[C@](C)(O)C=C)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(C)=C

InChI Identifier

InChI=1S/C42H70O14/c1-11-41(9,51)19-27(53-39-37(49)35(47)33(45)31(21-43)55-39)17-25(7)13-15-29(23(3)4)30(24(5)6)16-14-26(8)18-28(20-42(10,52)12-2)54-40-38(50)36(48)34(46)32(22-44)56-40/h11-12,17-18,27-40,43-52H,1-3,5,13-16,19-22H2,4,6-10H3/b25-17+,26-18+/t27-,28-,29+,30+,31-,32-,33-,34-,35+,36+,37-,38-,39-,40-,41-,42-/m1/s1

InChI Key

IAXMSBCBRWSXIH-AGKBTZFZSA-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
Amaranthus retroflexus	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
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Sesquiterpenoid
Farsesane sesquiterpenoid
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Fatty acyl
Monosaccharide
Oxane
Tertiary alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Acetal
Polyol
Alcohol
Organic oxygen compound
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
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	1.8	ChemAxon
pKa (Strongest Acidic)	11.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	239.22 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	211.74 m³·mol⁻¹	ChemAxon
Polarizability	87.36 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

101407083

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r,4s,5s,6r)-2-{[(3s,5s,6e,10r,11r,14e,16s,18s)-3,18-dihydroxy-3,7,14,18-tetramethyl-10,11-bis(prop-1-en-2-yl)-16-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icosa-1,6,14,19-tetraen-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0260155)

MOL for NP0260155 ((2r,3r,4s,5s,6r)-2-{[(3s,5s,6e,10r,11r,14e,16s,18s)-3,18-dihydroxy-3,7,14,18-tetramethyl-10,11-bis(prop-1-en-2-yl)-16-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icosa-1,6,14,19-tetraen-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0260155 ((2r,3r,4s,5s,6r)-2-{[(3s,5s,6e,10r,11r,14e,16s,18s)-3,18-dihydroxy-3,7,14,18-tetramethyl-10,11-bis(prop-1-en-2-yl)-16-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icosa-1,6,14,19-tetraen-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0260155 ((2r,3r,4s,5s,6r)-2-{[(3s,5s,6e,10r,11r,14e,16s,18s)-3,18-dihydroxy-3,7,14,18-tetramethyl-10,11-bis(prop-1-en-2-yl)-16-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icosa-1,6,14,19-tetraen-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0260155 ((2r,3r,4s,5s,6r)-2-{[(3s,5s,6e,10r,11r,14e,16s,18s)-3,18-dihydroxy-3,7,14,18-tetramethyl-10,11-bis(prop-1-en-2-yl)-16-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icosa-1,6,14,19-tetraen-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0260155 ((2r,3r,4s,5s,6r)-2-{[(3s,5s,6e,10r,11r,14e,16s,18s)-3,18-dihydroxy-3,7,14,18-tetramethyl-10,11-bis(prop-1-en-2-yl)-16-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icosa-1,6,14,19-tetraen-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0260155 ((2r,3r,4s,5s,6r)-2-{[(3s,5s,6e,10r,11r,14e,16s,18s)-3,18-dihydroxy-3,7,14,18-tetramethyl-10,11-bis(prop-1-en-2-yl)-16-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icosa-1,6,14,19-tetraen-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0260155 ((2r,3r,4s,5s,6r)-2-{[(3s,5s,6e,10r,11r,14e,16s,18s)-3,18-dihydroxy-3,7,14,18-tetramethyl-10,11-bis(prop-1-en-2-yl)-16-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icosa-1,6,14,19-tetraen-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0260155 ((2r,3r,4s,5s,6r)-2-{[(3s,5s,6e,10r,11r,14e,16s,18s)-3,18-dihydroxy-3,7,14,18-tetramethyl-10,11-bis(prop-1-en-2-yl)-16-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icosa-1,6,14,19-tetraen-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0260155 ((2r,3r,4s,5s,6r)-2-{[(3s,5s,6e,10r,11r,14e,16s,18s)-3,18-dihydroxy-3,7,14,18-tetramethyl-10,11-bis(prop-1-en-2-yl)-16-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icosa-1,6,14,19-tetraen-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0260155 ((2r,3r,4s,5s,6r)-2-{[(3s,5s,6e,10r,11r,14e,16s,18s)-3,18-dihydroxy-3,7,14,18-tetramethyl-10,11-bis(prop-1-en-2-yl)-16-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}icosa-1,6,14,19-tetraen-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)