NP-MRD: Showing NP-Card for 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 14-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraenoate (NP0225153)

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Record Information

Version

2.0

Created at

2022-09-06 03:47:43 UTC

Updated at

2022-09-06 03:47:43 UTC

NP-MRD ID

NP0225153

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 14-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraenoate

Description

3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl 14-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraenoate 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. 3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl 14-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraenoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261504172D          

 57 59  0  0  0  0            999 V2000
   -5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4138  -10.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -11.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579  -13.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868  -13.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158  -10.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302  -11.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447  -13.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592  -13.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737  -12.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737  -10.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447  -10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5888   -8.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638   -8.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8605   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5749   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2894   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8605   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5749   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  4  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  9 18  1  0  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
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  2  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  0  0  0  0
 35 34  1  4  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 41 39  1  4  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 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
 49 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  1  0  0  0  0
 47 56  1  0  0  0  0
 56 57  1  0  0  0  0
M  END

     RDKit          3D

119121  0  0  0  0  0  0  0  0999 V2000
   -1.5118    1.3713    1.9632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0439    0.1677    2.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8924   -0.4560    0.9899 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6133   -1.9690    1.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5695    0.0807   -0.3680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1059   -0.1554   -0.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8971    0.3947   -2.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0504    1.3396   -2.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0871    1.8373   -3.8063 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8152    1.9898   -1.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2630    1.7160   -1.8518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4527    0.2665   -1.8571 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576   -0.4205   -1.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3860   -1.9285   -1.3135 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848    0.1916   -0.3020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2263   -0.2246    1.1129 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2072    0.3727    1.9419 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2047   -1.6505    1.4021 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2328   -2.4153    1.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9161   -3.8808    1.8299 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6264   -2.0942    1.3957 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5107   -3.0364    1.5628 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2068   -0.8812    1.1104 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6034   -0.6778    1.0089 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8328   -0.1728   -0.2690 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1846    0.0372   -0.5151 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2774    0.7794   -1.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6004    1.0456   -2.1826 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8768    0.8493    0.5294 C   0  0  2  0  0  0  0  0  0  0  0  0
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   10.4961    0.5343    1.9380 C   0  0  1  0  0  0  0  0  0  0  0  0
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    8.9885    0.3861    2.0080 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.4651    1.5989    1.5029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2438   -0.3397    1.3051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7349    0.9358    1.3195 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2337    1.2258    2.5980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7533    2.5024    2.6577 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.1524    2.5033    3.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0464    1.9591    4.5344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6541    3.2547    1.3597 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4117    4.4269    1.5195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2037    2.5102    0.1818 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.5379    2.7775   -0.0449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9312    1.0226    0.3918 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7636    0.3576   -0.7973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7142   -0.6049   -1.0695 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0913   -1.8527   -1.1644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0041   -2.8994   -1.1406 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.3551   -3.3239    0.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2781   -4.3794    0.1553 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.9546   -3.6638   -2.3487 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.9828   -1.4683   -3.8453 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.6049    0.4092   -2.1047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6255    2.0614    1.1407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9051    1.7264    2.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8588   -0.4475    2.9250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5452   -2.1365    1.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9582   -2.4527    0.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1921   -2.3942    1.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7120    1.1753   -0.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1534   -0.3910   -1.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9138   -1.2650   -0.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4879    0.2578    0.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4882    0.0025   -2.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8358    1.6548   -4.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2769    2.9278   -3.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9645    1.3608   -4.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7410    1.6482   -0.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6787    3.0998   -1.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3514    2.1490   -2.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8935    2.3063   -1.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7806   -0.3289   -2.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6084   -2.4124   -0.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3950   -2.3399   -1.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1142   -2.1421   -2.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3013    1.3113   -0.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3992   -0.1022   -0.6736 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2353    0.1873    1.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1797    1.3563    1.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1955   -2.1215    1.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9093   -4.4370    0.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7085   -4.2416    2.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9657   -3.9595    2.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1774   -1.6017    1.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6897   -0.9551   -0.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7114    0.2738   -2.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7899    1.7698   -1.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1120    0.2165   -2.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7597    1.9384    0.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7214    1.2481    0.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


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M  END
> <DATABASE_ID>
NP0225153

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC=C(C)CC(O)C=C(C)C(=O)OC1OC(CO)C(O)C(O)C1O)=CCCC(C)(OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C38H62O19/c1-6-38(5,57-37-33(30(48)27(45)24(17-41)54-37)55-35-31(49)28(46)25(43)22(15-39)52-35)12-8-11-18(2)9-7-10-19(3)13-21(42)14-20(4)34(51)56-36-32(50)29(47)26(44)23(16-40)53-36/h6,10-11,14,21-33,35-37,39-50H,1,7-9,12-13,15-17H2,2-5H3

> <INCHI_KEY>
YGMLZIOKJMDMKW-UHFFFAOYSA-N

> <FORMULA>
C38H62O19

> <MOLECULAR_WEIGHT>
822.895

> <EXACT_MASS>
822.388529776

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
119

> <JCHEM_AVERAGE_POLARIZABILITY>
86.23850089429288

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 14-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraenoate

> <ALOGPS_LOGP>
-0.76

> <JCHEM_LOGP>
-1.6486035166666648

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.308041015492652

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.84088780545188

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6483775957536793

> <JCHEM_POLAR_SURFACE_AREA>
315.21

> <JCHEM_REFRACTIVITY>
198.3023000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
20

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 14-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraenoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0     -10.669 -12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -12.003 -13.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -12.003 -14.630   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.669 -15.400   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.669 -16.940   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.336 -17.710   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.106 -19.044   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -8.002 -18.480   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -8.002 -20.020   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -6.668 -20.790   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -6.668 -22.330   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335 -23.100   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.335 -24.640   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -8.002 -23.100   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -8.002 -24.640   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -9.336 -22.330   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -10.669 -23.100   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -9.336 -20.790   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0     -10.669 -20.020   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0     -12.003 -20.790   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0     -12.003 -22.330   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0     -13.337 -23.100   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -13.337 -24.640   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0     -14.670 -25.410   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0     -14.670 -22.330   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0     -16.004 -23.100   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0     -14.670 -20.790   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -16.004 -20.020   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0     -13.337 -20.020   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -13.337 -18.480   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -8.566 -16.376   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -7.026 -16.376   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -13.337 -10.780   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -14.670  -8.470   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -16.004  -6.160   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0     -14.670  -5.390   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0     -17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -17.338  -3.850   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -18.672  -3.080   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0     -18.672  -1.540   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0     -20.005  -3.850   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0     -21.339  -3.080   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0     -22.673  -3.850   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0     -24.006  -3.080   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -25.340  -3.850   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0     -26.674  -3.080   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0     -24.006  -1.540   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0     -25.340  -0.770   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0     -22.673  -0.770   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0     -22.673   0.770   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0     -21.339  -1.540   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0     -20.005  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   31                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    9   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   20   30                                                  
CONECT   30   29                                                            
CONECT   31    6   32                                                       
CONECT   32   31                                                            
CONECT   33    2   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48   56                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50   52                                                  
CONECT   50   49   51                                                       
CONECT   51   50                                                            
CONECT   52   49   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   47   57                                                  
CONECT   57   56                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  118    0
END

View in JSmol

Synonyms

Value	Source
3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl 14-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraenoic acid	Generator

Chemical Formula

C₃₈H₆₂O₁₉

Average Mass

822.8950 Da

Monoisotopic Mass

822.38853 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(CCC=C(C)CC(O)C=C(C)C(=O)OC1OC(CO)C(O)C(O)C1O)=CCCC(C)(OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O)C=C

InChI Identifier

InChI=1S/C38H62O19/c1-6-38(5,57-37-33(30(48)27(45)24(17-41)54-37)55-35-31(49)28(46)25(43)22(15-39)52-35)12-8-11-18(2)9-7-10-19(3)13-21(42)14-20(4)34(51)56-36-32(50)29(47)26(44)23(16-40)53-36/h6,10-11,14,21-33,35-37,39-50H,1,7-9,12-13,15-17H2,2-5H3

InChI Key

YGMLZIOKJMDMKW-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Diterpene glycoside
Diterpenoid
Terpene glycoside
Fatty acyl glycoside of mono- or disaccharide
Long chain fatty alcohol
Alkyl glycoside
Disaccharide
Glycosyl compound
O-glycosyl compound
Fatty alcohol
Fatty acid ester
Oxane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Acetal
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Primary alcohol
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	-0.76	ALOGPS
logP	-1.6	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	11.84	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	315.21 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	198.3 m³·mol⁻¹	ChemAxon
Polarizability	86.24 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 14-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraenoate (NP0225153)

MOL for NP0225153 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 14-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraenoate)

3D MOL for NP0225153 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 14-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraenoate)

3D SDF for NP0225153 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 14-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraenoate)

3D-SDF for NP0225153 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 14-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraenoate)

PDB for NP0225153 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 14-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraenoate)

3D PDB for NP0225153 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 14-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraenoate)

SMILES for NP0225153 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 14-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraenoate)

INCHI for NP0225153 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 14-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraenoate)

Structure for NP0225153 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 14-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraenoate)

3D Structure for NP0225153 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 14-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraenoate)