NP-MRD: Showing NP-Card for Squalamine (NP0070462)

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Record Information

Version

2.0

Created at

2022-04-28 15:51:57 UTC

Updated at

2022-04-28 15:51:58 UTC

NP-MRD ID

NP0070462

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Squalamine

Description

{[(3R,6R)-6-[(1S,2S,5S,7R,9R,10S,11S,14R,15R)-5-({3-[(4-aminobutyl)amino]propyl}amino)-9-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl]-2-methylheptan-3-yl]oxy}sulfonic acid belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. Squalamine is found in Squalus acanthias . Based on a literature review very few articles have been published on {[(3R,6R)-6-[(1S,2S,5S,7R,9R,10S,11S,14R,15R)-5-({3-[(4-aminobutyl)amino]propyl}amino)-9-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl]-2-methylheptan-3-yl]oxy}sulfonic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282217512D          

 43 46  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3570   -0.9826    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8419   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3570   -2.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6119   -0.1979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0599    0.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4189   -0.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6738    0.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4808    0.9297    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7357    1.7144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5427    1.8859    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3497    2.0574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7142    1.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3712    2.6929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0328    0.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8398    0.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7779   -0.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6586   -0.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -3.3000    0.0000 N   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
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  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
  4 10  1  0  0  0  0
  9 11  1  1  0  0  0
  8 12  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
  7 15  1  6  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  6  0  0  0
 16 19  1  6  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  2  0  0  0  0
 25 28  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 13 32  1  6  0  0  0
  5 33  1  6  0  0  0
  2 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 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
 42 43  1  0  0  0  0
M  END

     RDKit          3D

108111  0  0  0  0  0  0  0  0999 V2000
   -8.5979   -2.9538    1.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2951   -1.4625    1.2738 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.7359   -1.3888   -0.1770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8434   -1.2176    1.5199 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3306    0.1601    1.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4847    0.6859   -0.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9004    2.0676   -0.2872 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4834    3.1081    0.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5831    2.1996   -0.8146 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2155    3.6951   -0.9810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6997    3.7117   -1.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4124    2.2870   -1.3249 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0307    1.8501   -1.4629 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7394    0.4122   -1.2345 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7711   -0.3785   -0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1747    0.1302   -0.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3264    1.5896   -0.3131 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0023    1.7859    1.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6603    0.1975   -0.6521 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6702    0.4394    0.8152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1382   -1.2224   -0.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4727   -1.3192   -0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5058   -0.4005   -0.7949 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4178   -0.0280    0.2379 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6330    0.5879   -0.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6138   -0.2910   -0.8684 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0143   -1.4932   -0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9502   -2.3137   -0.7331 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2401   -1.6895   -0.9167 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9961   -1.5118    0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2633   -2.8270    1.0596 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0248   -2.5838    2.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2989   -1.9328    2.0902 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9677    0.7087   -1.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5514    1.0996   -1.4584 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3638    2.4864   -0.8659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0854    2.8529   -0.8721 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1586    4.0354   -1.6717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4622   -1.7224    2.7850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4163   -2.9991    2.6765 S   0  0  2  0  0  6  0  0  0  0  0  0
   -4.2489   -2.8610    3.6273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9249   -3.1525    1.2692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2115   -4.4214    3.1264 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.6284   -3.0991    2.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.9494   -0.8803    1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2554    0.5697   -2.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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  4 39  1  0
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  5 53  1  0
  6 54  1  0
  6 55  1  0
  7 56  1  6
  8 57  1  0
  8 58  1  0
  8 59  1  0
  9 60  1  6
 10 61  1  0
 10 62  1  0
 11 63  1  0
 11 64  1  0
 12 65  1  6
 13 66  1  6
 37106  1  1
 38107  1  0
 36104  1  0
 36105  1  0
 35103  1  6
 34101  1  0
 34102  1  0
 23 82  1  6
 22 80  1  0
 22 81  1  0
 21 78  1  0
 21 79  1  0
 20 75  1  0
 20 76  1  0
 20 77  1  0
 14 67  1  6
 15 68  1  0
 15 69  1  0
 16 70  1  0
 16 71  1  0
 18 72  1  0
 18 73  1  0
 18 74  1  0
 24 83  1  0
 25 84  1  0
 25 85  1  0
 26 86  1  0
 26 87  1  0
 27 88  1  0
 27 89  1  0
 28 90  1  0
 29 91  1  0
 29 92  1  0
 30 93  1  0
 30 94  1  0
 31 95  1  0
 31 96  1  0
 32 97  1  0
 32 98  1  0
 33 99  1  0
 33100  1  0
 43108  1  0
M  END


  Mrv1652304282217512D          

 43 46  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3570   -0.9826    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8419   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3570   -2.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6119   -0.1979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0599    0.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4189   -0.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6738    0.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4808    0.9297    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7357    1.7144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5427    1.8859    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3497    2.0574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7142    1.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3712    2.6929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0328    0.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8398    0.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7779   -0.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6586   -0.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -3.3000    0.0000 N   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
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  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
  4 10  1  0  0  0  0
  9 11  1  1  0  0  0
  8 12  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
  7 15  1  6  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  6  0  0  0
 16 19  1  6  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  2  0  0  0  0
 25 28  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 13 32  1  6  0  0  0
  5 33  1  6  0  0  0
  2 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 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
 42 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0070462

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](O)C[C@H]4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)NCCCNCCCCN)OS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C34H65N3O5S/c1-23(2)31(42-43(39,40)41)12-9-24(3)27-10-11-28-32-29(14-16-34(27,28)5)33(4)15-13-26(21-25(33)22-30(32)38)37-20-8-19-36-18-7-6-17-35/h23-32,36-38H,6-22,35H2,1-5H3,(H,39,40,41)/t24-,25-,26+,27-,28+,29+,30-,31-,32-,33+,34-/m1/s1

> <INCHI_KEY>
UIRKNQLZZXALBI-UARQPKAMSA-N

> <FORMULA>
C34H65N3O5S

> <MOLECULAR_WEIGHT>
627.97

> <EXACT_MASS>
627.464493379

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
108

> <JCHEM_AVERAGE_POLARIZABILITY>
76.4815599117828

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(3R,6R)-6-[(1S,2S,5S,7R,9R,10S,11S,14R,15R)-5-({3-[(4-aminobutyl)amino]propyl}amino)-9-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptan-3-yl]oxy}sulfonic acid

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
3.242448694206993

> <ALOGPS_LOGS>
-6.57

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.2590805271413066

> <JCHEM_PKA_STRONGEST_BASIC>
10.894395668948247

> <JCHEM_POLAR_SURFACE_AREA>
133.91

> <JCHEM_REFRACTIVITY>
174.42499999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.69e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(3R,6R)-6-[(1S,2S,5S,7R,9R,10S,11S,14R,15R)-5-({3-[(4-aminobutyl)amino]propyl}amino)-9-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptan-3-yl]oxysulfonic 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  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.133  -1.834   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.038  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.133  -4.326   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.609  -0.369   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -7.578   0.775   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -10.115  -0.049   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -10.591   1.415   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -12.097   1.736   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0     -12.573   3.200   0.000  0.00  0.00           O+0
HETATM   25  S   UNK     0     -14.080   3.520   0.000  0.00  0.00           S+0
HETATM   26  O   UNK     0     -15.586   3.841   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0     -14.400   2.014   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0     -13.760   5.027   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0     -13.128   0.591   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -14.634   0.911   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -12.652  -0.874   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.829  -0.778   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       1.334  -6.930   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0       6.668  -6.930   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   43  N   UNK     0      13.337  -6.160   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   33                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   15                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9                                                            
CONECT   12    8   13   18                                                  
CONECT   13   12   14   16   32                                             
CONECT   14   13   15                                                       
CONECT   15   14    7                                                       
CONECT   16   13   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   12                                                       
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25                                                            
CONECT   29   23   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   13                                                            
CONECT   33    5                                                            
CONECT   34    2   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
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                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

View in JSmol

Synonyms

Value	Source
{[(3R,6R)-6-[(1S,2S,5S,7R,9R,10S,11S,14R,15R)-5-({3-[(4-aminobutyl)amino]propyl}amino)-9-hydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl]-2-methylheptan-3-yl]oxy}sulfonate	Generator
{[(3R,6R)-6-[(1S,2S,5S,7R,9R,10S,11S,14R,15R)-5-({3-[(4-aminobutyl)amino]propyl}amino)-9-hydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl]-2-methylheptan-3-yl]oxy}sulphonate	Generator
{[(3R,6R)-6-[(1S,2S,5S,7R,9R,10S,11S,14R,15R)-5-({3-[(4-aminobutyl)amino]propyl}amino)-9-hydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl]-2-methylheptan-3-yl]oxy}sulphonic acid	Generator

Chemical Formula

C₃₄H₆₅N₃O₅S

Average Mass

627.9700 Da

Monoisotopic Mass

627.46449 Da

IUPAC Name

{[(3R,6R)-6-[(1S,2S,5S,7R,9R,10S,11S,14R,15R)-5-({3-[(4-aminobutyl)amino]propyl}amino)-9-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptan-3-yl]oxy}sulfonic acid

Traditional Name

[(3R,6R)-6-[(1S,2S,5S,7R,9R,10S,11S,14R,15R)-5-({3-[(4-aminobutyl)amino]propyl}amino)-9-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptan-3-yl]oxysulfonic acid

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](O)C[C@H]4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)NCCCNCCCCN)OS(O)(=O)=O

InChI Identifier

InChI=1S/C34H65N3O5S/c1-23(2)31(42-43(39,40)41)12-9-24(3)27-10-11-28-32-29(14-16-34(27,28)5)33(4)15-13-26(21-25(33)22-30(32)38)37-20-8-19-36-18-7-6-17-35/h23-32,36-38H,6-22,35H2,1-5H3,(H,39,40,41)/t24-,25-,26+,27-,28+,29+,30-,31-,32-,33+,34-/m1/s1

InChI Key

UIRKNQLZZXALBI-UARQPKAMSA-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
Squalus acanthias	Animalia	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Monohydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Monohydroxy bile acid, alcohol, or derivatives
Sulfated steroid skeleton
Steroidal alkaloid
Pregnane-type alkaloid
7-hydroxysteroid
Hydroxysteroid
Azasteroid
Alkaloid or derivatives
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Organic sulfuric acid or derivatives
Cyclic alcohol
Secondary alcohol
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	2.48	ALOGPS
logP	3.24	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	-1.3	ChemAxon
pKa (Strongest Basic)	10.89	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	133.91 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	174.42 m³·mol⁻¹	ChemAxon
Polarizability	76.48 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

15298097

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Squalamine (NP0070462)

MOL for NP0070462 (Squalamine)

3D MOL for NP0070462 (Squalamine)

3D SDF for NP0070462 (Squalamine)

3D-SDF for NP0070462 (Squalamine)

PDB for NP0070462 (Squalamine)

3D PDB for NP0070462 (Squalamine)

SMILES for NP0070462 (Squalamine)

INCHI for NP0070462 (Squalamine)

Structure for NP0070462 (Squalamine)

3D Structure for NP0070462 (Squalamine)