NP-MRD: Showing NP-Card for (-)-Crypthophilic acid B (NP0076369)

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Record Information

Version

2.0

Created at

2022-04-28 21:30:49 UTC

Updated at

2022-04-28 21:30:50 UTC

NP-MRD ID

NP0076369

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Crypthophilic acid B

Description

(3R,12S)-12-{[(2R,3R,4S,5S,6R)-3-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-{[(2S)-2-methylbutanoyl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3-hydroxyhexadecanoic 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. (-)-Crypthophilic acid B is found in Scrophularia crypthophila and Scrophularia cryptophila. Based on a literature review very few articles have been published on (3R,12S)-12-{[(2R,3R,4S,5S,6R)-3-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-{[(2S)-2-methylbutanoyl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3-hydroxyhexadecanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223302D          

 68 71  0  0  1  0            999 V2000
    0.5291   -8.6464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2810   -8.8023    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5510   -9.5819    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0109  -10.2055    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7992  -10.0496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0692   -9.2700    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8794   -9.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1494   -8.3346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393  -10.6732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2810  -10.9851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3612   -9.7378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6312  -10.5173    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0911  -11.1410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3612  -11.9205    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1713  -12.0764    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7114  -11.4528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4413  -10.6732    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9814  -10.0496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5215  -11.6087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4413  -12.8560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2515  -13.0119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7916  -12.3882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5215  -13.7914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3317  -13.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6017  -14.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9814  -14.4151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8211  -12.5442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8211   -8.1787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5510   -7.3991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2591   -7.2432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5291   -6.4637    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0109   -5.8400    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8211   -5.9959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0911   -6.7755    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9013   -6.9314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4413   -6.3077    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2515   -6.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7916   -5.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6017   -5.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1418   -5.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9519   -5.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4920   -4.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3021   -5.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8422   -4.4368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6524   -4.5927    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.1925   -3.9691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5427   -3.5014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2726   -4.9046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9224   -5.3723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1713   -5.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7114   -4.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4413   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9814   -3.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2591   -5.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0692   -4.9046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7992   -3.5014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0692   -2.7218    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8794   -2.5659    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4195   -3.1895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1494   -3.9691    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6895   -4.5927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2296   -3.0336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1494   -1.7863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5291   -2.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393   -6.3077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7992   -7.8668    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
  7  8  1  0  0  0  0
  5  9  1  1  0  0  0
  4 10  1  6  0  0  0
  3 11  1  1  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
 16 19  1  1  0  0  0
 15 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  1  0  0  0
 14 27  1  1  0  0  0
  2 28  1  6  0  0  0
 29 28  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  6  0  0  0
 36 35  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  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  2  0  0  0  0
 47 49  1  0  0  0  0
 45 50  1  1  0  0  0
 36 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
 32 55  1  6  0  0  0
 55 56  1  0  0  0  0
 57 56  1  6  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 57 62  1  0  0  0  0
 62 63  1  1  0  0  0
 61 64  1  1  0  0  0
 60 65  1  6  0  0  0
 59 66  1  1  0  0  0
 31 67  1  1  0  0  0
 30 68  1  6  0  0  0
M  END

     RDKit          3D

148151  0  0  0  0  0  0  0  0999 V2000
    5.9494   -4.6122   -2.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9598   -4.9948   -1.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5914   -4.4112   -1.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6191   -4.8353   -0.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2289   -4.2578   -0.4959 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3487   -4.7679    0.6014 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8061   -4.3831    1.9783 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8780   -2.8982    2.2292 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3233   -2.6040    3.6483 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3794   -1.1267    3.9422 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0468   -0.4537    3.7985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1093    1.0396    4.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5641    1.2594    5.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6057    2.7365    5.8732 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4544    3.4487    5.0622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7952    3.3175    5.9601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7502    4.7645    6.2893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2838    5.4367    6.4566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9976    5.4115    6.4196 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1362   -2.9198   -0.5273 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9300   -2.2265   -1.6700 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9228   -1.2725   -1.7614 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0385   -0.6814   -2.9609 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6963    0.6792   -2.9530 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9355    0.7954   -2.4651 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1127    0.5397   -1.1235 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3902    1.8488   -0.5567 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9177    1.7304    0.7033 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4044    2.8931    1.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5760    0.4552    1.4167 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1700    0.4761    2.6732 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1687   -0.7288    0.6617 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3294   -1.8242    0.7119 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3095   -0.2707   -0.7874 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5323   -1.3725   -1.5732 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6361   -0.4138   -3.5127 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3256   -1.4660   -4.3703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3701   -0.2600   -2.4101 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0475    0.8150   -1.6181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4449   -1.5688   -1.5969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3779   -2.3782   -2.2095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5237   -2.5549   -1.4412 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7078   -3.8697   -1.1960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8814   -4.2115   -0.5525 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8855   -5.6885   -0.2785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8300   -6.0920    0.5326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1003   -3.7858   -1.3386 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0562   -3.1308   -0.5780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6755   -2.9591   -2.5462 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0222   -3.7919   -3.4773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7123   -1.9040   -2.1233 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2853   -0.9172   -1.3343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2094    0.3572   -1.8077 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6168    1.2225   -0.8821 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9317    2.5367   -1.0838 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8549    3.5079   -0.6519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2131    2.8216   -2.5746 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1745    4.2214   -2.6841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2360    4.8900   -3.4668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4250    4.1408   -4.0687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1613    6.3630   -3.6086 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8503    6.6578   -4.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2541    6.9286   -4.4939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5875    6.5715   -3.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5414    2.1924   -2.8641 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7240    1.8488   -4.1933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5972    0.9016   -2.0458 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3935   -0.0485   -2.6284 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9181   -4.2305   -1.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1923   -5.5452   -2.7563 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5073   -3.8362   -2.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3506   -4.5668   -0.1411 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9205   -6.0987   -0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6860   -3.3280   -1.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2059   -4.7746   -2.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0234   -4.5815    0.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5364   -5.9338   -0.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9364   -4.6345   -1.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2647   -5.8871    0.5871 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282223302D          

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 59 66  1  1  0  0  0
 31 67  1  1  0  0  0
 30 68  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0076369

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC[C@@H](CCCCCCCC[C@@H](O)CC(O)=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)[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](OC(=O)[C@@H](C)CC)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C45H80O23/c1-6-8-16-25(17-14-12-10-9-11-13-15-24(47)18-28(48)49)63-44-39(34(55)31(52)27(65-44)20-60-42-36(57)32(53)29(50)22(4)61-42)68-45-40(33(54)30(51)26(19-46)64-45)67-43-37(58)35(56)38(23(5)62-43)66-41(59)21(3)7-2/h21-27,29-40,42-47,50-58H,6-20H2,1-5H3,(H,48,49)/t21-,22-,23-,24+,25-,26+,27+,29-,30+,31+,32+,33-,34-,35-,36+,37+,38-,39+,40+,42+,43-,44+,45-/m0/s1

> <INCHI_KEY>
ANAGMXSUOWSSPU-LRLRJSSPSA-N

> <FORMULA>
C45H80O23

> <MOLECULAR_WEIGHT>
989.112

> <EXACT_MASS>
988.509038836

> <JCHEM_ACCEPTOR_COUNT>
22

> <JCHEM_ATOM_COUNT>
148

> <JCHEM_AVERAGE_POLARIZABILITY>
104.45591978498499

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,12S)-12-{[(2R,3R,4S,5S,6R)-3-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-{[(2S)-2-methylbutanoyl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3-hydroxyhexadecanoic acid

> <ALOGPS_LOGP>
0.50

> <JCHEM_LOGP>
0.7787467349999974

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.866770282880351

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.671850139336751

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6489650165973497

> <JCHEM_POLAR_SURFACE_AREA>
359.97

> <JCHEM_REFRACTIVITY>
229.78830000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
28

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.87e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,12S)-12-{[(2R,3R,4S,5S,6R)-3-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-{[(2S)-2-methylbutanoyl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3-hydroxyhexadecanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  O   UNK     0       0.988 -16.140   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.525 -16.431   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.029 -17.886   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.020 -19.050   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.492 -18.759   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.996 -17.304   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.508 -17.013   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.012 -15.558   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       2.500 -19.923   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -0.525 -20.505   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -2.541 -18.177   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.045 -19.632   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.037 -20.796   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.541 -22.252   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.053 -22.543   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.061 -21.379   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.557 -19.923   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.565 -18.759   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -6.574 -21.670   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -4.557 -23.998   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -6.069 -24.289   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -7.078 -23.125   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -6.574 -25.744   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -8.086 -26.035   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -8.590 -27.490   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.565 -26.908   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.533 -23.416   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.533 -15.267   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.029 -13.812   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.484 -13.521   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.988 -12.065   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.020 -10.901   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.533 -11.192   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -2.037 -12.648   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -3.549 -12.939   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -4.557 -11.774   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -6.069 -12.065   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -7.078 -10.901   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -8.590 -11.192   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -9.598 -10.028   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -11.110 -10.319   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -12.118  -9.155   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -13.631  -9.446   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -14.639  -8.282   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -16.151  -8.573   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -17.159  -7.409   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -18.672  -7.700   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0     -19.680  -6.536   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0     -19.176  -9.155   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0     -16.655 -10.028   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      -4.053 -10.319   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -5.061  -9.155   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -4.557  -7.700   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -5.565  -6.536   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       0.484  -9.446   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       1.996  -9.155   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0       2.500  -7.700   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0       1.492  -6.536   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0       1.996  -5.081   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       3.508  -4.790   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       4.516  -5.954   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       4.012  -7.409   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0       5.020  -8.573   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0       6.029  -5.663   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0       4.012  -3.335   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0       0.988  -3.917   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0       2.500 -11.774   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0       1.492 -14.685   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   28                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5                                                            
CONECT   10    4                                                            
CONECT   11    3   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17                                                            
CONECT   19   16                                                            
CONECT   20   15   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23                                                            
CONECT   27   14                                                            
CONECT   28    2   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31   68                                                  
CONECT   31   30   32   67                                                  
CONECT   32   31   33   55                                                  
CONECT   33   32   34                                                       
CONECT   34   33   29   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   51                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
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   50                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47                                                            
CONECT   50   45                                                            
CONECT   51   36   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53                                                            
CONECT   55   32   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58   62                                                  
CONECT   58   57   59                                                       
CONECT   59   58   60   66                                                  
CONECT   60   59   61   65                                                  
CONECT   61   60   62   64                                                  
CONECT   62   61   57   63                                                  
CONECT   63   62                                                            
CONECT   64   61                                                            
CONECT   65   60                                                            
CONECT   66   59                                                            
CONECT   67   31                                                            
CONECT   68   30                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  142    0
END

View in JSmol

Synonyms

Value	Source
(3R,12S)-12-{[(2R,3R,4S,5S,6R)-3-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-{[(2S)-2-methylbutanoyl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3-hydroxyhexadecanoate	Generator

Chemical Formula

C₄₅H₈₀O₂₃

Average Mass

989.1120 Da

Monoisotopic Mass

988.50904 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CCCC[C@@H](CCCCCCCC[C@@H](O)CC(O)=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)[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](OC(=O)[C@@H](C)CC)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C45H80O23/c1-6-8-16-25(17-14-12-10-9-11-13-15-24(47)18-28(48)49)63-44-39(34(55)31(52)27(65-44)20-60-42-36(57)32(53)29(50)22(4)61-42)68-45-40(33(54)30(51)26(19-46)64-45)67-43-37(58)35(56)38(23(5)62-43)66-41(59)21(3)7-2/h21-27,29-40,42-47,50-58H,6-20H2,1-5H3,(H,48,49)/t21-,22-,23-,24+,25-,26+,27+,29-,30+,31+,32+,33-,34-,35-,36+,37+,38-,39+,40+,42+,43-,44+,45-/m0/s1

InChI Key

ANAGMXSUOWSSPU-LRLRJSSPSA-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
Scrophularia crypthophila	Plant	KNApSAcK
Scrophularia cryptophila	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 ester
Branched fatty acid
Beta-hydroxy acid
Oxane
Hydroxy acid
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
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	0.5	ALOGPS
logP	0.78	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	4.67	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	22	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	359.97 Å²	ChemAxon
Rotatable Bond Count	28	ChemAxon
Refractivity	229.79 m³·mol⁻¹	ChemAxon
Polarizability	104.46 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

163103386

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Crypthophilic acid B (NP0076369)

MOL for NP0076369 ((-)-Crypthophilic acid B)

3D MOL for NP0076369 ((-)-Crypthophilic acid B)

3D SDF for NP0076369 ((-)-Crypthophilic acid B)

3D-SDF for NP0076369 ((-)-Crypthophilic acid B)

PDB for NP0076369 ((-)-Crypthophilic acid B)

3D PDB for NP0076369 ((-)-Crypthophilic acid B)

SMILES for NP0076369 ((-)-Crypthophilic acid B)

INCHI for NP0076369 ((-)-Crypthophilic acid B)

Structure for NP0076369 ((-)-Crypthophilic acid B)

3D Structure for NP0076369 ((-)-Crypthophilic acid B)