NP-MRD: Showing NP-Card for n-(1-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-16-methyloctadec-4-en-2-yl)-2-hydroxytetracosanimidic acid (NP0219282)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 20:13:29 UTC

Updated at

2022-09-05 20:13:30 UTC

NP-MRD ID

NP0219282

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-(1-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-16-methyloctadec-4-en-2-yl)-2-hydroxytetracosanimidic acid

Description

N-(1-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-16-methyloctadec-4-en-2-yl)-2-hydroxytetracosanimidic acid belongs to the class of organic compounds known as glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines are compounds containing a sphingosine linked to a simple glucosyl moiety. n-(1-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-16-methyloctadec-4-en-2-yl)-2-hydroxytetracosanimidic acid is found in Luidia maculata. N-(1-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-16-methyloctadec-4-en-2-yl)-2-hydroxytetracosanimidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004261504342D          

 70 71  0  0  0  0            999 V2000
    4.2579  -17.3798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -17.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6828  -17.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4262  -17.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1077  -17.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8511  -17.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5326  -17.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2760  -17.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9575  -16.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7009  -17.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3824  -16.8433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1258  -17.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8073  -16.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5507  -17.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2322  -16.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9756  -16.9864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6571  -16.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4006  -16.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0820  -16.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8255  -16.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5069  -16.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2504  -16.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9318  -16.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8699  -15.3768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6753  -16.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7372  -17.3798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3568  -16.0922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1002  -16.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1621  -17.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4807  -17.7375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5426  -18.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8611  -19.0252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9231  -19.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2416  -20.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3036  -21.1355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6665  -20.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7285  -21.0282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4719  -21.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1534  -20.9209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8968  -21.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5783  -20.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3217  -21.1713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9588  -22.1012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7022  -22.4589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2773  -22.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3392  -23.3889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5339  -22.2085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8524  -22.6735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3480  -19.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0914  -20.0982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2860  -18.9179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9675  -18.4529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7817  -15.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7197  -15.1622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5251  -16.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2066  -15.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9500  -16.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6315  -15.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3749  -16.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0564  -15.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7998  -16.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4813  -15.5556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2247  -15.9133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9062  -15.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6496  -15.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3311  -15.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0745  -15.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1365  -16.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7560  -15.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4994  -15.5914    0.0000 C   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
  6  7  1  0  0  0  0
  7  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
 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
 17 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
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  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
 34 35  1  0  0  0  0
 33 36  1  0  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
 40 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
 38 47  1  0  0  0  0
 47 48  1  0  0  0  0
 36 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
 31 51  1  0  0  0  0
 51 52  1  0  0  0  0
 28 53  1  0  0  0  0
 53 54  1  0  0  0  0
 55 53  1  4  0  0  0
 55 56  2  0  0  0  0
 56 57  1  0  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
 62 63  1  0  0  0  0
 63 64  1  0  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
 67 69  1  0  0  0  0
 69 70  1  0  0  0  0
M  END


  Mrv1533004261504342D          

 70 71  0  0  0  0            999 V2000
    4.2579  -17.3798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013  -17.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6828  -17.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4262  -17.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1077  -17.1652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8511  -17.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5326  -17.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2760  -17.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9575  -16.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7009  -17.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3824  -16.8433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1258  -17.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8073  -16.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5507  -17.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2322  -16.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9756  -16.9864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6571  -16.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4006  -16.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0820  -16.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8255  -16.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5069  -16.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2504  -16.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9318  -16.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8699  -15.3768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6753  -16.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7372  -17.3798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3568  -16.0922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1002  -16.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1621  -17.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4807  -17.7375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5426  -18.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8611  -19.0252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9231  -19.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2416  -20.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3036  -21.1355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6665  -20.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7285  -21.0282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4719  -21.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1534  -20.9209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8968  -21.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5783  -20.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3217  -21.1713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9588  -22.1012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7022  -22.4589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2773  -22.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3392  -23.3889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5339  -22.2085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8524  -22.6735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3480  -19.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0914  -20.0982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2860  -18.9179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9675  -18.4529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7817  -15.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7197  -15.1622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5251  -16.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2066  -15.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9500  -16.2352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6315  -15.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3749  -16.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0564  -15.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7998  -16.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4813  -15.5556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2247  -15.9133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9062  -15.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6496  -15.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3311  -15.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0745  -15.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1365  -16.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7560  -15.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4994  -15.5914    0.0000 C   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
  6  7  1  0  0  0  0
  7  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
 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
 17 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
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  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
 34 35  1  0  0  0  0
 33 36  1  0  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
 40 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
 38 47  1  0  0  0  0
 47 48  1  0  0  0  0
 36 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
 31 51  1  0  0  0  0
 51 52  1  0  0  0  0
 28 53  1  0  0  0  0
 53 54  1  0  0  0  0
 55 53  1  4  0  0  0
 55 56  2  0  0  0  0
 56 57  1  0  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
 62 63  1  0  0  0  0
 63 64  1  0  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
 67 69  1  0  0  0  0
 69 70  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219282

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCCCCCCCC(O)C(=O)NC(COC1OC(CO)C(OC2OC(CO)C(O)C(O)C2O)C(O)C1O)C(O)C=CCCCCCCCCCCC(C)CC

> <INCHI_IDENTIFIER>
InChI=1S/C55H105NO14/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25-28-31-34-37-44(60)53(66)56-42(43(59)36-33-30-27-24-22-21-23-26-29-32-35-41(3)5-2)40-67-54-51(65)49(63)52(46(39-58)69-54)70-55-50(64)48(62)47(61)45(38-57)68-55/h33,36,41-52,54-55,57-65H,4-32,34-35,37-40H2,1-3H3,(H,56,66)

> <INCHI_KEY>
CGFYLVORONLSQF-UHFFFAOYSA-N

> <FORMULA>
C55H105NO14

> <MOLECULAR_WEIGHT>
1004.438

> <EXACT_MASS>
1003.753507065

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
175

> <JCHEM_AVERAGE_POLARIZABILITY>
122.97045384206758

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(1-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-16-methyloctadec-4-en-2-yl)-2-hydroxytetracosanamide

> <ALOGPS_LOGP>
6.88

> <JCHEM_LOGP>
10.296186348

> <ALOGPS_LOGS>
-5.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.307223562922964

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.839291493147597

> <JCHEM_PKA_STRONGEST_BASIC>
-3.171400568585562

> <JCHEM_POLAR_SURFACE_AREA>
248.08999999999997

> <JCHEM_REFRACTIVITY>
273.4511

> <JCHEM_ROTATABLE_BOND_COUNT>
44

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.56e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(1-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-16-methyloctadec-4-en-2-yl)-2-hydroxytetracosanamide

> <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       7.948 -32.442   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336 -33.110   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.608 -32.242   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.996 -32.910   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.268 -32.042   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.655 -32.709   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.927 -31.841   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.315 -32.509   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.587 -31.641   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.975 -32.309   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.247 -31.441   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.635 -32.108   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.907 -31.241   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.295 -31.908   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.567 -31.040   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.955 -31.708   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.227 -30.840   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      30.614 -31.508   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      31.886 -30.640   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      33.274 -31.307   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      34.546 -30.439   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      35.934 -31.107   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      37.206 -30.239   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      37.090 -28.703   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      38.594 -30.907   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      38.709 -32.442   0.000  0.00  0.00           O+0
HETATM   27  N   UNK     0      39.866 -30.039   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      41.254 -30.706   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      41.369 -32.242   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      40.097 -33.110   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      40.213 -34.646   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      38.941 -35.514   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      39.056 -37.049   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      37.784 -37.917   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      37.900 -39.453   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      40.444 -37.717   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      40.560 -39.253   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      41.948 -39.920   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      43.220 -39.052   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      44.607 -39.720   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      45.879 -38.852   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      47.267 -39.520   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      44.723 -41.256   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      46.111 -41.923   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      43.451 -42.124   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      43.567 -43.659   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      42.063 -41.456   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      40.791 -42.324   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      41.716 -36.849   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      43.104 -37.517   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      41.601 -35.313   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      42.873 -34.445   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      42.526 -29.838   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      42.410 -28.303   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      43.914 -30.506   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      45.186 -29.638   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      46.573 -30.306   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      47.845 -29.438   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      49.233 -30.105   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      50.505 -29.237   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      51.893 -29.905   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      53.165 -29.037   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      54.553 -29.705   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      55.825 -28.837   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      57.213 -29.505   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      58.485 -28.637   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      59.872 -29.304   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      59.988 -30.840   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      61.145 -28.436   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      62.532 -29.104   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   53                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   51                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   37   49                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   47                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   43                                                  
CONECT   41   40   42                                                       
CONECT   42   41                                                            
CONECT   43   40   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   38   48                                                  
CONECT   48   47                                                            
CONECT   49   36   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   31   52                                                  
CONECT   52   51                                                            
CONECT   53   28   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   64                                                       
CONECT   64   63   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65   67                                                       
CONECT   67   66   68   69                                                  
CONECT   68   67                                                            
CONECT   69   67   70                                                       
CONECT   70   69                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  142    0
END

View in JSmol

Synonyms

Value	Source
N-(1-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-16-methyloctadec-4-en-2-yl)-2-hydroxytetracosanimidate	Generator

Chemical Formula

C₅₅H₁₀₅NO₁₄

Average Mass

1004.4380 Da

Monoisotopic Mass

1003.75351 Da

IUPAC Name

N-(1-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-16-methyloctadec-4-en-2-yl)-2-hydroxytetracosanamide

Traditional Name

N-(1-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-16-methyloctadec-4-en-2-yl)-2-hydroxytetracosanamide

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCCCCCCC(O)C(=O)NC(COC1OC(CO)C(OC2OC(CO)C(O)C(O)C2O)C(O)C1O)C(O)C=CCCCCCCCCCCC(C)CC

InChI Identifier

InChI=1S/C55H105NO14/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25-28-31-34-37-44(60)53(66)56-42(43(59)36-33-30-27-24-22-21-23-26-29-32-35-41(3)5-2)40-67-54-51(65)49(63)52(46(39-58)69-54)70-55-50(64)48(62)47(61)45(38-57)68-55/h33,36,41-52,54-55,57-65H,4-32,34-35,37-40H2,1-3H3,(H,56,66)

InChI Key

CGFYLVORONLSQF-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Luidia maculata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines are compounds containing a sphingosine linked to a simple glucosyl moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Sphingolipids

Sub Class

Glycosphingolipids

Direct Parent

Glycosyl-N-acylsphingosines

Alternative Parents

Substituents

Glycosyl-n-acylsphingosine
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Disaccharide
Glycosyl compound
O-glycosyl compound
Fatty amide
N-acyl-amine
Oxane
Fatty acyl
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Organoheterocyclic compound
Polyol
Oxacycle
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Organonitrogen compound
Carbonyl group
Organooxygen compound
Primary 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	6.88	ALOGPS
logP	10.3	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	11.84	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	248.09 Å²	ChemAxon
Rotatable Bond Count	44	ChemAxon
Refractivity	273.45 m³·mol⁻¹	ChemAxon
Polarizability	122.97 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74074889

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-(1-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-16-methyloctadec-4-en-2-yl)-2-hydroxytetracosanimidic acid (NP0219282)

MOL for NP0219282 (n-(1-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-16-methyloctadec-4-en-2-yl)-2-hydroxytetracosanimidic acid)

3D MOL for NP0219282 (n-(1-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-16-methyloctadec-4-en-2-yl)-2-hydroxytetracosanimidic acid)

3D SDF for NP0219282 (n-(1-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-16-methyloctadec-4-en-2-yl)-2-hydroxytetracosanimidic acid)

3D-SDF for NP0219282 (n-(1-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-16-methyloctadec-4-en-2-yl)-2-hydroxytetracosanimidic acid)

PDB for NP0219282 (n-(1-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-16-methyloctadec-4-en-2-yl)-2-hydroxytetracosanimidic acid)

3D PDB for NP0219282 (n-(1-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-16-methyloctadec-4-en-2-yl)-2-hydroxytetracosanimidic acid)

SMILES for NP0219282 (n-(1-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-16-methyloctadec-4-en-2-yl)-2-hydroxytetracosanimidic acid)

INCHI for NP0219282 (n-(1-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-16-methyloctadec-4-en-2-yl)-2-hydroxytetracosanimidic acid)

Structure for NP0219282 (n-(1-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-16-methyloctadec-4-en-2-yl)-2-hydroxytetracosanimidic acid)

3D Structure for NP0219282 (n-(1-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-16-methyloctadec-4-en-2-yl)-2-hydroxytetracosanimidic acid)