NP-MRD: Showing NP-Card for (-)-Cuscutic acid D (NP0079465)

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Record Information

Version

2.0

Created at

2022-04-29 00:29:37 UTC

Updated at

2022-04-29 00:29:37 UTC

NP-MRD ID

NP0079465

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Cuscutic acid D

Description

(11S)-11-{[(2R,3R,4S,5R,6R)-3-{[(2S,3R,4R,5R,6R)-3-{[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4R,5S,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-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadecanoic acid belongs to the class of organic compounds known as sophorolipids. These are glycolipids containing a sophorose moiety linked glycosidically to the hydroxyl group of a 17-hydroxy-C18 saturated fatty acid. The carboxyl group of the fatty acid can be linked to the 4'-hydroxyl of the second glucose to form a lactone. (-)-Cuscutic acid D is found in Cuscuta chinensis . Based on a literature review very few articles have been published on (11S)-11-{[(2R,3R,4S,5R,6R)-3-{[(2S,3R,4R,5R,6R)-3-{[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4R,5S,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-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadecanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202292D          

 61 64  0  0  1  0            999 V2000
   -6.4639    8.5316    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9722    7.8691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1526    7.9638    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8248    8.7208    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3165    9.3833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1361    9.2886    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6278    9.9511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9887   10.1404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0053    8.8155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6774    9.5725    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1692   10.2350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8413   10.9921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0218   11.0867    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5301   10.4243    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579    9.6672    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3662    9.0047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7105   10.5189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3827   11.2760    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8744   11.9384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5466   12.6955    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7270   12.7901    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2353   12.1277    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5631   11.3706    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0714   10.7082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5842   12.2223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3992   13.5472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0383   13.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6940   11.8438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3331   11.6545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6609    7.3013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9887    6.5443    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4970    5.8818    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8248    5.1248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6444    5.0301    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1361    5.6926    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8083    6.4496    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3000    7.1121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9557    5.5979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9722    4.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7917    4.1784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6774    5.9765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1857    5.3140    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5135    4.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0218    3.8945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3496    3.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1857    1.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3662    5.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8744    4.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0549    4.8408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5631    4.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2564    4.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7482    3.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5677    3.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0594    3.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8790    3.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3707    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1903    2.5696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429    1.7179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2835    8.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7752    9.0994    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  6  0  0  0
  5  8  1  1  0  0  0
  4  9  1  1  0  0  0
 10  9  1  6  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  1  0  0  0
 14 17  1  1  0  0  0
 18 17  1  6  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  1  0  0  0
 22 25  1  1  0  0  0
 21 26  1  1  0  0  0
 20 27  1  1  0  0  0
 13 28  1  6  0  0  0
 12 29  1  1  0  0  0
  3 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  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  6  0  0  0
 35 38  1  6  0  0  0
 34 39  1  6  0  0  0
 39 40  1  0  0  0  0
 32 41  1  6  0  0  0
 42 41  1  6  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
 42 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  2  0  0  0  0
 57 59  1  0  0  0  0
  1 60  1  6  0  0  0
 60 61  1  0  0  0  0
M  END

     RDKit          3D

133136  0  0  0  0  0  0  0  0999 V2000
   -6.7887    2.2361   -2.8422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4967    2.9508   -3.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3722    2.1103   -3.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9983    0.9524   -2.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6260    1.5730   -1.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0098    0.7698   -0.2151 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5075   -0.3385    0.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0048   -1.6330    0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3556   -1.8191   -0.5089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4404   -1.3602    0.4484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8067   -1.5882   -0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0668   -0.8390   -1.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4113   -1.0437   -1.9704 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6315   -0.5009   -1.3541 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9351   -0.8598    0.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3147   -0.3146    0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9548    0.3231   -0.4866 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8018   -0.5627    1.6299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5862    0.7413   -0.4433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8289    1.5504    0.2515 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2188    2.6014   -0.4665 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2134    3.5882    0.4009 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5563    4.0674   -0.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0394    5.0658    0.7836 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2189    3.1944    1.8361 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1535    4.0387    2.5020 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149    1.8019    2.0945 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1219    1.8379    2.1393 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3025    0.8854    0.9482 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1592   -0.4099    1.3544 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1321   -1.2615    0.8356 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6230   -2.3043    0.1957 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1892   -3.5354    0.2673 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3569   -4.6167   -0.4029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0621   -5.8089   -0.2262 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5682   -4.0288    1.6314 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7165   -5.0413    2.0173 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5100   -2.8643    2.6388 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2412   -3.2786    3.7554 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1187   -1.7183    1.9271 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2232   -2.1773    1.1815 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2938   -1.3359    1.2181 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5373   -0.9668   -0.1263 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0693   -2.0916   -0.7693 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7653   -1.9699   -2.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5733   -2.1630   -0.4709 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9489   -3.4729   -0.4672 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7701   -1.4567    0.8868 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8152   -0.1002    0.7126 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9911    0.5051    1.1398 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8137    1.7782    1.6545 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3005    2.6391    0.6817 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5494    3.7747    1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4761    3.2166   -0.0703 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9253    4.3220    0.6511 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5134    2.0962   -0.1046 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.3865    2.1390    0.9544 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7614    0.7632   -0.1965 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7055   -0.2119   -0.4201 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5812   -1.8734    1.7659 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7214   -1.4894    3.0753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3161    2.4740   -1.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5272    2.5607   -3.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6949    1.1341   -2.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6554    3.7672   -3.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2541    3.4724   -2.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5875    1.7546   -4.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4712    2.7933   -3.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0774    0.5017   -3.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8666    0.3087   -2.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9833    2.4708   -1.5723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5157    2.0995   -0.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9271    1.6071    0.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3875    0.0896    1.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7613   -0.4720    1.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0681   -2.2689    1.0685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3053   -2.2512   -0.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4892   -1.5072   -1.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5560   -2.9509   -0.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3633   -0.2731    0.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3830   -2.0002    1.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8849   -2.7173   -0.3952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5744   -1.4443    0.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9199    0.2598   -1.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3311   -1.0886   -2.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4056   -0.6957   -3.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5258   -2.1848   -2.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5449   -0.7537   -2.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6304    0.6534   -1.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2453   -0.3039    0.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9136   -1.9057    0.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2112   -0.3027    2.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4418    2.1093    1.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
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 60132  1  1
 61133  1  0
M  END


  Mrv1652304292202292D          

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 60 61  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0079465

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC[C@@H](CCCCCCCCCC(O)=O)O[C@@H]1O[C@H](CO)[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/C40H72O21/c1-4-5-11-14-21(15-12-9-7-6-8-10-13-16-24(43)44)56-39-35(30(50)27(47)22(17-41)57-39)61-40-36(31(51)28(48)23(18-42)58-40)60-38-33(53)34(26(46)20(3)55-38)59-37-32(52)29(49)25(45)19(2)54-37/h19-23,25-42,45-53H,4-18H2,1-3H3,(H,43,44)/t19-,20-,21-,22+,23+,25+,26-,27-,28-,29+,30-,31+,32+,33+,34+,35+,36+,37-,38-,39+,40-/m0/s1

> <INCHI_KEY>
IIIBAFGYJYVDRT-HOGBDARISA-N

> <FORMULA>
C40H72O21

> <MOLECULAR_WEIGHT>
888.995

> <EXACT_MASS>
888.456609338

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_ATOM_COUNT>
133

> <JCHEM_AVERAGE_POLARIZABILITY>
93.16199264583898

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.00

> <JCHEM_LOGP>
-0.11965839866666511

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.869158665765728

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.952019602669778

> <JCHEM_PKA_STRONGEST_BASIC>
-3.648674368288396

> <JCHEM_POLAR_SURFACE_AREA>
333.67

> <JCHEM_REFRACTIVITY>
205.3189

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.98e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(11S)-11-{[(2R,3R,4S,5R,6R)-3-{[(2S,3R,4R,5R,6R)-3-{[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-{[(2S,3R,4R,5S,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-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadecanoic 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     -12.066  15.926   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0     -11.148  14.689   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -9.618  14.866   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.006  16.279   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.924  17.515   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -11.454  17.339   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0     -12.372  18.575   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -9.312  18.929   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -7.476  16.456   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -6.865  17.869   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -7.782  19.105   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -7.171  20.519   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.641  20.695   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.723  19.459   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335  18.045   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.417  16.809   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -3.193  19.635   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.581  21.048   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.499  22.285   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.887  23.698   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.357  23.875   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.439  22.638   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.051  21.225   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.133  19.989   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.091  22.815   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -0.745  25.288   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.805  24.935   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -5.029  22.108   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -8.088  21.755   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -8.700  13.629   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -9.312  12.216   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -8.394  10.979   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -9.006   9.566   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0     -10.536   9.390   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -11.454  10.626   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -10.842  12.039   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0     -11.760  13.276   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0     -12.984  10.449   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0     -11.148   7.976   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0     -12.678   7.800   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -6.865  11.156   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -5.947   9.920   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -6.559   8.506   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -5.641   7.270   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -6.253   5.857   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -5.947   3.207   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -4.417  10.096   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -3.499   8.860   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -1.969   9.036   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -1.051   7.800   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       0.479   7.976   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       1.397   6.740   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       2.926   6.916   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       3.844   5.680   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       5.374   5.857   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       6.292   4.620   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0       7.822   4.797   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0       5.680   3.207   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0     -13.596  15.749   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0     -14.514  16.986   0.000  0.00  0.00           O+0
CONECT    1    2    6   60                                                  
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   41                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   39                                                  
CONECT   35   34   36   38                                                  
CONECT   36   35   31   37                                                  
CONECT   37   36                                                            
CONECT   38   35                                                            
CONECT   39   34   40                                                       
CONECT   40   39                                                            
CONECT   41   32   42                                                       
CONECT   42   41   43   48                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46                                                            
CONECT   48   42   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57                                                            
CONECT   60    1   61                                                       
CONECT   61   60                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  128    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₄₀H₇₂O₂₁

Average Mass

888.9950 Da

Monoisotopic Mass

888.45661 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CCCCC[C@@H](CCCCCCCCCC(O)=O)O[C@@H]1O[C@H](CO)[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/C40H72O21/c1-4-5-11-14-21(15-12-9-7-6-8-10-13-16-24(43)44)56-39-35(30(50)27(47)22(17-41)57-39)61-40-36(31(51)28(48)23(18-42)58-40)60-38-33(53)34(26(46)20(3)55-38)59-37-32(52)29(49)25(45)19(2)54-37/h19-23,25-42,45-53H,4-18H2,1-3H3,(H,43,44)/t19-,20-,21-,22+,23+,25+,26-,27-,28-,29+,30-,31+,32+,33+,34+,35+,36+,37-,38-,39+,40-/m0/s1

InChI Key

IIIBAFGYJYVDRT-HOGBDARISA-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 sophorolipids. These are glycolipids containing a sophorose moiety linked glycosidically to the hydroxyl group of a 17-hydroxy-C18 saturated fatty acid. The carboxyl group of the fatty acid can be linked to the 4'-hydroxyl of the second glucose to form a lactone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Sophorolipids

Alternative Parents

Substituents

Sophorolipid
Oligosaccharide
Long-chain fatty acid
O-glycosyl compound
Glycosyl compound
Hydroxy fatty acid
Heterocyclic fatty acid
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	ALOGPS
logP	-0.12	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	333.67 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	205.32 m³·mol⁻¹	ChemAxon
Polarizability	93.16 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

162918362

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-Cuscutic acid D (NP0079465)

MOL for NP0079465 ((-)-Cuscutic acid D)

3D MOL for NP0079465 ((-)-Cuscutic acid D)

3D SDF for NP0079465 ((-)-Cuscutic acid D)

3D-SDF for NP0079465 ((-)-Cuscutic acid D)

PDB for NP0079465 ((-)-Cuscutic acid D)

3D PDB for NP0079465 ((-)-Cuscutic acid D)

SMILES for NP0079465 ((-)-Cuscutic acid D)

INCHI for NP0079465 ((-)-Cuscutic acid D)

Structure for NP0079465 ((-)-Cuscutic acid D)

3D Structure for NP0079465 ((-)-Cuscutic acid D)