NP-MRD: Showing NP-Card for (2s)-4-amino-n-[(1r,2s,3r,4r,5s)-5-amino-4-{[(2r,3r,4r,5s,6r)-6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[(2s,3r,4r,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl]-2-hydroxybutanimidic acid (NP0211031)

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Record Information

Version

2.0

Created at

2022-09-05 09:07:35 UTC

Updated at

2022-09-05 09:07:35 UTC

NP-MRD ID

NP0211031

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-4-amino-n-[(1r,2s,3r,4r,5s)-5-amino-4-{[(2r,3r,4r,5s,6r)-6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[(2s,3r,4r,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl]-2-hydroxybutanimidic acid

Description

(2S)-4-amino-N-[(1R,2S,3R,4R,5S)-5-amino-4-{[(2R,3R,4R,5S,6R)-6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl]-2-hydroxybutanimidic acid belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars. (2s)-4-amino-n-[(1r,2s,3r,4r,5s)-5-amino-4-{[(2r,3r,4r,5s,6r)-6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[(2s,3r,4r,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl]-2-hydroxybutanimidic acid is found in Streptomyces fradiae. Based on a literature review very few articles have been published on (2S)-4-amino-N-[(1R,2S,3R,4R,5S)-5-amino-4-{[(2R,3R,4R,5S,6R)-6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl]-2-hydroxybutanimidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052211072D          

 41 43  0  0  1  0            999 V2000
    0.6078    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    5.5902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    4.3527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    4.7652    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4656    4.3527    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4656    3.5277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    3.1152    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8946    3.5277    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8946    4.3527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    3.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    2.2902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3235    1.8777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0380    2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0380    3.1152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7525    1.8777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7525    1.0527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4669    2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1814    1.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8959    2.2902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    1.8777    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8946    1.0527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    2.2902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4656    1.8777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.0527    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1331    0.5678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8781   -0.2169    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3631   -0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0275   -1.6380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0531   -0.2169    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5682   -0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7982    0.5678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0136    0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    4.7652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    5.5902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8946    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    6.8277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    6.0027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4656    6.8277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    5.5902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0367    6.0027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  2  0  0  0  0
 14 15  1  4  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
  8 23  1  0  0  0  0
 23 24  1  1  0  0  0
 25 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 25 32  1  0  0  0  0
 32 33  1  1  0  0  0
  6 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 36 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  1  6  0  0  0
 38 40  1  0  0  0  0
  5 40  1  0  0  0  0
 40 41  1  1  0  0  0
M  END

     RDKit          3D

 84 86  0  0  0  0  0  0  0  0999 V2000
   -3.3792    2.6557   -1.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4798    1.2279   -0.9355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2953    0.3771   -1.6611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8416    0.7737    0.0800 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9819   -0.6072    0.4484 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7148   -1.3298    0.7340 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7536   -0.5504    1.3915 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3834   -0.4380    0.6690 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5608   -1.1728    1.3484 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1609   -2.3229    2.0671 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5090   -1.4761    0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0628   -0.1801   -0.2718 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9442   -0.3233   -1.3749 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2578   -1.3721   -2.0062 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7319   -2.6015   -1.6617 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2101   -1.3479   -3.1573 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5045   -0.0013   -3.4231 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4845   -2.0977   -2.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2543   -3.5490   -2.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5691   -4.2265   -3.6821 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0315    0.8701   -0.6047 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7206    2.0800   -0.5754 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9303    0.9460    0.4301 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0207    1.9249    0.2291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0486    2.9334    1.1788 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3660    3.0476    1.6494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4321    4.2906    2.2703 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8681    4.6542    2.4648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5958    4.7365    1.2964 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6622    5.2092    1.3842 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4767    6.0376    0.6127 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1453    4.2564    0.4946 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4687    4.6767    0.4342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9164   -2.5273    1.3248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1076   -3.1303    1.3964 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3093   -4.0337    0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6109   -4.7200    0.2366 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2871   -2.2440    1.6452 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9259   -2.5079    2.8442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8817   -0.7809    1.6582 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9624    0.0725    1.6800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3578    3.1449   -1.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5550    3.1754   -0.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1639    2.6381   -2.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2581    0.5520   -1.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5074   -1.1877   -0.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2371   -1.5820   -0.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2628   -0.9530   -0.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0626   -0.4629    2.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6078   -2.4811    2.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9147   -3.1554    1.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8400   -1.9715   -0.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3140   -2.1254    0.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6551    0.2316    0.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1317   -3.1539   -2.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7387   -1.7389   -4.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4699    0.1163   -3.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9978   -1.6062   -2.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1156   -1.9883   -3.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7123   -3.7029   -1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2575   -4.0448   -2.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6830   -3.7665   -3.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1998   -4.2839   -4.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6796    0.6958   -1.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2392    2.1870   -1.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4649    1.2104    1.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6706    2.8373    1.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9766    4.1805    3.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3558    3.9049    3.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9746    5.6302    2.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3912    5.3206    1.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0310    5.8067    2.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9025    6.4666   -0.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3339    4.2579   -0.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7037    4.7478   -0.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0683   -3.8409    2.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5704   -4.8885    0.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2644   -3.5066   -0.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3261   -4.2213   -0.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9439   -4.8190    1.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0180   -2.3709    0.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3113   -2.4432    3.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2452   -0.6237    2.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0442    0.5846    2.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 12 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 27 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
  6 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 35 38  1  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 40  5  1  0
 23  8  1  0
 32 25  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  3 45  1  0
  5 46  1  6
  6 47  1  6
  8 48  1  6
  9 49  1  1
 10 50  1  0
 10 51  1  0
 11 52  1  0
 11 53  1  0
 12 54  1  1
 15 55  1  0
 16 56  1  6
 17 57  1  0
 18 58  1  0
 18 59  1  0
 19 60  1  0
 19 61  1  0
 20 62  1  0
 20 63  1  0
 21 64  1  6
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 25 67  1  1
 27 68  1  1
 28 69  1  0
 28 70  1  0
 29 71  1  0
 30 72  1  1
 31 73  1  0
 32 74  1  6
 33 75  1  0
 35 76  1  1
 36 77  1  0
 36 78  1  0
 37 79  1  0
 37 80  1  0
 38 81  1  6
 39 82  1  0
 40 83  1  1
 41 84  1  0
M  END


  Mrv1652309052211072D          

 41 43  0  0  1  0            999 V2000
    0.6078    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    5.5902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    4.3527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    4.7652    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4656    4.3527    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4656    3.5277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    3.1152    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8946    3.5277    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8946    4.3527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    3.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    2.2902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3235    1.8777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0380    2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0380    3.1152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7525    1.8777    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7525    1.0527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4669    2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1814    1.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8959    2.2902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    1.8777    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8946    1.0527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    2.2902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4656    1.8777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.0527    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1331    0.5678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8781   -0.2169    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3631   -0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0275   -1.6380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0531   -0.2169    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5682   -0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7982    0.5678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0136    0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    4.7652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    5.5902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8946    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    6.8277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    6.0027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4656    6.8277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    5.5902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0367    6.0027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  2  0  0  0  0
 14 15  1  4  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
  8 23  1  0  0  0  0
 23 24  1  1  0  0  0
 25 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 25 32  1  0  0  0  0
 32 33  1  1  0  0  0
  6 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 36 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  1  6  0  0  0
 38 40  1  0  0  0  0
  5 40  1  0  0  0  0
 40 41  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0211031

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)=N[C@H]1[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N=C(O)[C@@H](O)CCN)[C@H](O)[C@H]2O[C@@H]2O[C@H](CO)[C@H](O)[C@H]2O)O[C@H](CN)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H43N5O13/c1-7(30)27-13-17(35)15(33)11(5-25)38-22(13)40-19-8(26)4-9(28-21(37)10(31)2-3-24)14(32)20(19)41-23-18(36)16(34)12(6-29)39-23/h8-20,22-23,29,31-36H,2-6,24-26H2,1H3,(H,27,30)(H,28,37)/t8-,9+,10-,11+,12+,13+,14-,15+,16-,17+,18+,19+,20+,22+,23-/m0/s1

> <INCHI_KEY>
YWZWUOBLFGEYKH-PVIDWHMVSA-N

> <FORMULA>
C23H43N5O13

> <MOLECULAR_WEIGHT>
597.619

> <EXACT_MASS>
597.285736465

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
59.53321588290267

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-4-amino-N-[(1R,2S,3R,4R,5S)-5-amino-4-{[(2R,3R,4R,5S,6R)-6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl]-2-hydroxybutanimidic acid

> <JCHEM_LOGP>
-11.285062837103371

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
3

> <JCHEM_PKA>
5.7163788849624355

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7091831968956321

> <JCHEM_PKA_STRONGEST_BASIC>
9.990807712297288

> <JCHEM_POLAR_SURFACE_AREA>
321.77

> <JCHEM_REFRACTIVITY>
134.36570000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-4-amino-N-[(1R,2S,3R,4R,5S)-5-amino-4-{[(2R,3R,4R,5S,6R)-6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl]-2-hydroxybutanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       1.134   8.125   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.468   8.895   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.468  10.435   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       3.802   8.125   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.136   8.895   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.469   8.125   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.469   6.585   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.803   5.815   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.137   6.585   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       9.137   8.125   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      10.470   5.815   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.470   4.275   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      11.804   3.505   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      13.138   4.275   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.138   5.815   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      14.471   3.505   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      14.471   1.965   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      15.805   4.275   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.139   3.505   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      18.472   4.275   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       9.137   3.505   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.137   1.965   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.803   4.275   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.469   3.505   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.469   1.965   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.715   1.060   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.239  -0.405   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.144  -1.651   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.518  -3.058   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.699  -0.405   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.794  -1.651   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.223   1.060   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.759   1.536   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       7.803   8.895   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.803  10.435   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.137  11.205   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0       9.137  12.745   0.000  0.00  0.00           N+0
HETATM   38  C   UNK     0       6.469  11.205   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       6.469  12.745   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       5.136  10.435   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       3.802  11.205   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   40                                                  
CONECT    6    5    7   34                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   23                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   12   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    8   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   25   33                                                  
CONECT   33   32                                                            
CONECT   34    6   35                                                       
CONECT   35   34   36   38                                                  
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   35   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38    5   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END

View in JSmol

Synonyms

Value	Source
(2S)-4-Amino-N-[(1R,2S,3R,4R,5S)-5-amino-4-{[(2R,3R,4R,5S,6R)-6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[(2S,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl]-2-hydroxybutanimidate	Generator

Chemical Formula

C₂₃H₄₃N₅O₁₃

Average Mass

597.6190 Da

Monoisotopic Mass

597.28574 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(O)=N[C@H]1[C@@H](O[C@@H]2[C@@H](N)C[C@@H](N=C(O)[C@@H](O)CCN)[C@H](O)[C@H]2O[C@@H]2O[C@H](CO)[C@H](O)[C@H]2O)O[C@H](CN)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C23H43N5O13/c1-7(30)27-13-17(35)15(33)11(5-25)38-22(13)40-19-8(26)4-9(28-21(37)10(31)2-3-24)14(32)20(19)41-23-18(36)16(34)12(6-29)39-23/h8-20,22-23,29,31-36H,2-6,24-26H2,1H3,(H,27,30)(H,28,37)/t8-,9+,10-,11+,12+,13+,14-,15+,16-,17+,18+,19+,20+,22+,23-/m0/s1

InChI Key

YWZWUOBLFGEYKH-PVIDWHMVSA-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

Species Name	Source	Reference
Streptomyces fradiae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Aminoglycosides

Alternative Parents

Substituents

Neamine core
N-acyl-alpha-hexosamine
Glycosyl compound
O-glycosyl compound
Aminocyclitol or derivatives
Cyclohexanol
Cyclohexylamine
Cyclitol or derivatives
Monosaccharide
Oxane
Tetrahydrofuran
1,3-aminoalcohol
Cyclic alcohol
Secondary alcohol
Carboximidic acid
Carboximidic acid derivative
Propargyl-type 1,3-dipolar organic compound
Oxacycle
Organoheterocyclic compound
Acetal
Organic 1,3-dipolar compound
Alcohol
Primary alcohol
Organopnictogen compound
Primary amine
Hydrocarbon derivative
Amine
Primary aliphatic amine
Organic nitrogen compound
Organonitrogen compound
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

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

163019546

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-4-amino-n-[(1r,2s,3r,4r,5s)-5-amino-4-{[(2r,3r,4r,5s,6r)-6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[(2s,3r,4r,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl]-2-hydroxybutanimidic acid (NP0211031)

MOL for NP0211031 ((2s)-4-amino-n-[(1r,2s,3r,4r,5s)-5-amino-4-{[(2r,3r,4r,5s,6r)-6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[(2s,3r,4r,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl]-2-hydroxybutanimidic acid)

3D MOL for NP0211031 ((2s)-4-amino-n-[(1r,2s,3r,4r,5s)-5-amino-4-{[(2r,3r,4r,5s,6r)-6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[(2s,3r,4r,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl]-2-hydroxybutanimidic acid)

3D SDF for NP0211031 ((2s)-4-amino-n-[(1r,2s,3r,4r,5s)-5-amino-4-{[(2r,3r,4r,5s,6r)-6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[(2s,3r,4r,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl]-2-hydroxybutanimidic acid)

3D-SDF for NP0211031 ((2s)-4-amino-n-[(1r,2s,3r,4r,5s)-5-amino-4-{[(2r,3r,4r,5s,6r)-6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[(2s,3r,4r,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl]-2-hydroxybutanimidic acid)

PDB for NP0211031 ((2s)-4-amino-n-[(1r,2s,3r,4r,5s)-5-amino-4-{[(2r,3r,4r,5s,6r)-6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[(2s,3r,4r,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl]-2-hydroxybutanimidic acid)

3D PDB for NP0211031 ((2s)-4-amino-n-[(1r,2s,3r,4r,5s)-5-amino-4-{[(2r,3r,4r,5s,6r)-6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[(2s,3r,4r,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl]-2-hydroxybutanimidic acid)

SMILES for NP0211031 ((2s)-4-amino-n-[(1r,2s,3r,4r,5s)-5-amino-4-{[(2r,3r,4r,5s,6r)-6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[(2s,3r,4r,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl]-2-hydroxybutanimidic acid)

INCHI for NP0211031 ((2s)-4-amino-n-[(1r,2s,3r,4r,5s)-5-amino-4-{[(2r,3r,4r,5s,6r)-6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[(2s,3r,4r,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl]-2-hydroxybutanimidic acid)

Structure for NP0211031 ((2s)-4-amino-n-[(1r,2s,3r,4r,5s)-5-amino-4-{[(2r,3r,4r,5s,6r)-6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[(2s,3r,4r,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl]-2-hydroxybutanimidic acid)

3D Structure for NP0211031 ((2s)-4-amino-n-[(1r,2s,3r,4r,5s)-5-amino-4-{[(2r,3r,4r,5s,6r)-6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[(2s,3r,4r,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl]-2-hydroxybutanimidic acid)