NP-MRD: Showing NP-Card for (-)-Cuscutic acid B (NP0079463)

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Record Information

Version

2.0

Created at

2022-04-29 00:29:31 UTC

Updated at

2022-04-29 00:29:31 UTC

NP-MRD ID

NP0079463

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Cuscutic acid B

Description

(11S)-11-{[(2S,3R,4S,5R)-3-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}tetradecanoic acid belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety. (-)-Cuscutic acid B is found in Cuscuta chinensis . Based on a literature review very few articles have been published on (11S)-11-{[(2S,3R,4S,5R)-3-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}tetradecanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202292D          

 57 60  0  0  1  0            999 V2000
   16.4085    1.3267    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.7849    1.8668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9408    2.6769    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.7203    2.9470    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.3440    2.4069    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.1881    1.5967    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.8117    1.0567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1235    2.6769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8762    3.7571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6558    4.0271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.2794    3.4871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0590    3.7571    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.2149    4.5672    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.5912    5.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.8117    4.8373    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.1881    5.3774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7472    5.9175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5267    6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.1503    5.6474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9299    5.9175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.0858    6.7276    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.4622    7.2677    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.6826    6.9976    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.0590    7.5377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6181    8.0778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8654    6.9976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5535    5.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9944    4.8373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6826    3.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3171    3.2170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5376    2.9470    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.3817    2.1368    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.6021    1.8668    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9785    2.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1344    3.2170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9139    3.4871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.0698    4.2972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4462    4.8373    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.6667    4.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0430    5.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2635    4.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6398    5.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8603    5.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2366    5.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4571    5.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8334    5.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0539    5.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6507    5.9175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5861    6.9976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6021    5.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9785    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1344    6.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4462    1.0567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0053    1.5967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2526    0.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4730    0.2465    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  5  8  1  1  0  0  0
  4  9  1  6  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  6  0  0  0
 14 17  1  6  0  0  0
 18 17  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
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  6  0  0  0
 22 25  1  6  0  0  0
 21 26  1  1  0  0  0
 20 27  1  6  0  0  0
 13 28  1  1  0  0  0
 12 29  1  6  0  0  0
  3 30  1  1  0  0  0
 31 30  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 31 36  1  0  0  0  0
 36 37  1  1  0  0  0
 38 37  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 48 50  1  0  0  0  0
 38 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 33 54  1  6  0  0  0
 32 55  1  1  0  0  0
  1 56  1  1  0  0  0
 56 57  1  0  0  0  0
M  END

     RDKit          3D

123126  0  0  0  0  0  0  0  0999 V2000
    6.2915   -4.4600    1.8994 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8959   -3.8755    1.7789 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0630   -2.5122    1.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7914   -1.8140    0.9062 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7719   -0.4752    0.3273 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2090   -0.0017   -0.9444 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5628    0.1758   -1.4685 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4816   -0.9487   -1.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7995   -0.5851   -2.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4878    0.4904   -1.5034 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8092    0.8293   -2.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5242    1.8946   -1.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7599    3.1735   -1.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5533    4.1687   -0.5479 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6878    3.8409   -0.1203 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0781    5.4258   -0.3005 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642   -2.5855    0.1301 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7474   -2.9165    0.8779 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6511   -4.3006    0.9382 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7337   -4.9136   -0.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9254   -4.1435   -1.3399 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2626   -5.0700   -2.1377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1326   -3.3032   -0.6476 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.5356   -2.2667    0.2292 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3990   -1.9152    1.2029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7569   -0.5894    1.2028 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4859    0.0825    2.3893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9685   -0.5059    3.5237 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0563   -1.6135    4.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1844   -1.0588    4.3457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4045   -0.9390    3.4705 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.6620    0.7750    1.1314 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4415    2.5910   -1.7682 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5928    1.9651   -2.8548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8232    2.0117   -1.8678 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4490    2.6692   -2.9473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6251    2.1499   -0.6197 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7407    1.3502   -0.6163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9342    2.0202   -0.3726 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.5231    1.5413    0.8243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5046    2.4254    1.2341 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.8332    3.6233    1.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3955    2.8890    0.1204 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.6666   -0.1132    0.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6790    1.0314   -1.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5821   -0.6077   -1.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5417    0.7591   -2.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4941   -1.9293    5.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0987   -0.1614    3.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0198   -2.8099    4.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9114   -1.5362    2.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9326   -3.2926    1.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5943   -0.9920    0.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5048    0.3908   -0.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6337    2.6352   -3.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.0767    1.9097    2.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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  3  4  1  0
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  5  6  1  0
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  8  9  1  0
  9 10  1  0
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 27 93  1  6
 29 94  1  1
 30 95  1  0
 30 96  1  0
 31 97  1  0
 32 98  1  1
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 34100  1  1
 35101  1  0
 36102  1  6
 38103  1  6
 40104  1  6
 41105  1  0
 41106  1  0
 41107  1  0
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 44110  1  1
 46111  1  1
 48112  1  1
 49113  1  0
 49114  1  0
 49115  1  0
 50116  1  6
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 52118  1  1
 53119  1  0
 54120  1  6
 55121  1  0
 56122  1  1
 57123  1  0
M  END


  Mrv1652304292202292D          

 57 60  0  0  1  0            999 V2000
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   15.7849    1.8668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   16.7203    2.9470    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.3440    2.4069    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.1881    1.5967    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.8117    1.0567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1235    2.6769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8762    3.7571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6558    4.0271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.2794    3.4871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   19.2149    4.5672    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.5912    5.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.8117    4.8373    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   20.1503    5.6474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   21.0858    6.7276    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.4622    7.2677    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.6826    6.9976    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   19.9944    4.8373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   15.3171    3.2170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5376    2.9470    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.3817    2.1368    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.6021    1.8668    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9785    2.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1344    3.2170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9139    3.4871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.0698    4.2972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4462    4.8373    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.6667    4.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0430    5.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2635    4.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6398    5.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8603    5.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2366    5.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4571    5.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8334    5.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0539    5.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6507    5.9175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5861    6.9976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6021    5.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9785    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1344    6.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4462    1.0567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0053    1.5967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2526    0.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4730    0.2465    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  5  8  1  1  0  0  0
  4  9  1  6  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  6  0  0  0
 14 17  1  6  0  0  0
 18 17  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
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  6  0  0  0
 22 25  1  6  0  0  0
 21 26  1  1  0  0  0
 20 27  1  6  0  0  0
 13 28  1  1  0  0  0
 12 29  1  6  0  0  0
  3 30  1  1  0  0  0
 31 30  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 31 36  1  0  0  0  0
 36 37  1  1  0  0  0
 38 37  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 48 50  1  0  0  0  0
 38 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 33 54  1  6  0  0  0
 32 55  1  1  0  0  0
  1 56  1  1  0  0  0
 56 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0079463

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC[C@@H](CCCCCCCCCC(O)=O)O[C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C37H66O20/c1-4-12-19(13-10-8-6-5-7-9-11-14-22(40)41)53-36-32(25(44)20(39)16-50-36)57-37-33(28(47)26(45)21(15-38)54-37)56-35-30(49)31(24(43)18(3)52-35)55-34-29(48)27(46)23(42)17(2)51-34/h17-21,23-39,42-49H,4-16H2,1-3H3,(H,40,41)/t17-,18-,19-,20+,21+,23-,24-,25-,26-,27+,28-,29+,30+,31+,32+,33+,34-,35-,36-,37-/m0/s1

> <INCHI_KEY>
HPMIZGDBXRXSCK-JBGMGAEZSA-N

> <FORMULA>
C37H66O20

> <MOLECULAR_WEIGHT>
830.915

> <EXACT_MASS>
830.414744525

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
123

> <JCHEM_AVERAGE_POLARIZABILITY>
86.4467547443142

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(11S)-11-{[(2S,3R,4S,5R)-3-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}tetradecanoic acid

> <ALOGPS_LOGP>
-0.20

> <JCHEM_LOGP>
-0.3784607866666657

> <ALOGPS_LOGS>
-2.19

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.87431063588655

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.952019603289592

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6190506864636207

> <JCHEM_POLAR_SURFACE_AREA>
313.44

> <JCHEM_REFRACTIVITY>
190.15440000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.42e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(11S)-11-{[(2S,3R,4S,5R)-3-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}tetradecanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      30.629   2.477   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      29.465   3.485   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      29.756   4.997   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.211   5.501   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      32.375   4.493   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.084   2.981   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      33.248   1.972   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      33.831   4.997   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      31.502   7.013   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      32.957   7.517   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      34.122   6.509   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      35.577   7.013   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      35.868   8.526   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      34.704   9.534   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      33.248   9.030   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      32.084  10.038   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      34.995  11.046   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      36.450  11.550   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      37.614  10.542   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      39.069  11.046   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      39.360  12.558   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      38.196  13.566   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      36.741  13.062   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      35.577  14.070   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      38.487  15.079   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      40.815  13.062   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      40.233  10.038   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      37.323   9.030   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      36.741   6.005   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      28.592   6.005   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      27.137   5.501   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      26.846   3.989   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      25.391   3.485   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      24.226   4.493   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      24.518   6.005   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      25.973   6.509   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      26.264   8.021   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      25.100   9.030   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      23.644   8.526   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      22.480   9.534   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      21.025   9.030   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      19.861  10.038   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      18.406   9.534   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      17.242  10.542   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      15.787  10.038   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      14.622  11.046   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      13.167  10.542   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      12.003  11.550   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      10.548  11.046   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      12.294  13.062   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      25.391  10.542   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      24.226  11.550   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      24.518  13.062   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      25.100   1.972   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      28.010   2.981   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      30.338   0.964   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      28.883   0.460   0.000  0.00  0.00           O+0
CONECT    1    2    6   56                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   29                                                  
CONECT   13   12   14   28                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   10   16                                                  
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22   18   24                                                  
CONECT   24   23                                                            
CONECT   25   22                                                            
CONECT   26   21                                                            
CONECT   27   20                                                            
CONECT   28   13                                                            
CONECT   29   12                                                            
CONECT   30    3   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33   55                                                  
CONECT   33   32   34   54                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   31   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   51                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48                                                            
CONECT   51   38   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52                                                            
CONECT   54   33                                                            
CONECT   55   32                                                            
CONECT   56    1   57                                                       
CONECT   57   56                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  120    0
END

View in JSmol

Synonyms

Value	Source
(11S)-11-{[(2S,3R,4S,5R)-3-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl]oxy}tetradecanoate	Generator

Chemical Formula

C₃₇H₆₆O₂₀

Average Mass

830.9150 Da

Monoisotopic Mass

830.41474 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CCC[C@@H](CCCCCCCCCC(O)=O)O[C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)[C@H]1O

InChI Identifier

InChI=1S/C37H66O20/c1-4-12-19(13-10-8-6-5-7-9-11-14-22(40)41)53-36-32(25(44)20(39)16-50-36)57-37-33(28(47)26(45)21(15-38)54-37)56-35-30(49)31(24(43)18(3)52-35)55-34-29(48)27(46)23(42)17(2)51-34/h17-21,23-39,42-49H,4-16H2,1-3H3,(H,40,41)/t17-,18-,19-,20+,21+,23-,24-,25-,26-,27+,28-,29+,30+,31+,32+,33+,34-,35-,36-,37-/m0/s1

InChI Key

HPMIZGDBXRXSCK-JBGMGAEZSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Cuscuta chinensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Saccharolipids

Sub Class

Not Available

Direct Parent

Saccharolipids

Alternative Parents

Substituents

Oligosaccharide
Saccharolipid
Long-chain fatty acid
O-glycosyl compound
Glycosyl compound
Hydroxy fatty acid
Heterocyclic fatty acid
Fatty acyl
Fatty acid
Oxane
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-0.2	ALOGPS
logP	-0.38	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	313.44 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	190.15 m³·mol⁻¹	ChemAxon
Polarizability	86.45 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162980152

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Cuscutic acid B (NP0079463)

MOL for NP0079463 ((-)-Cuscutic acid B)

3D MOL for NP0079463 ((-)-Cuscutic acid B)

3D SDF for NP0079463 ((-)-Cuscutic acid B)

3D-SDF for NP0079463 ((-)-Cuscutic acid B)

PDB for NP0079463 ((-)-Cuscutic acid B)

3D PDB for NP0079463 ((-)-Cuscutic acid B)

SMILES for NP0079463 ((-)-Cuscutic acid B)

INCHI for NP0079463 ((-)-Cuscutic acid B)

Structure for NP0079463 ((-)-Cuscutic acid B)

3D Structure for NP0079463 ((-)-Cuscutic acid B)