NP-MRD: Showing NP-Card for 4-amino-n-(5-amino-4-{[6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl)-2-hydroxybutanimidic acid (NP0282179)

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Record Information

Version

2.0

Created at

2022-09-09 08:55:09 UTC

Updated at

2022-09-09 08:55:10 UTC

NP-MRD ID

NP0282179

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

4-Amino-N-(5-amino-4-{[6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl)-2-hydroxybutanimidic acid belongs to the class of organic compounds known as 4,5-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that are glycosidically linked to a pyranose of furanose unit at the C4- and C5-positions. 4-amino-n-(5-amino-4-{[6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl)-2-hydroxybutanimidic acid is found in Streptomyces fradiae. 4-Amino-N-(5-amino-4-{[6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl)-2-hydroxybutanimidic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191516592D          

 41 43  0  0  0  0            999 V2000
   -5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   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
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 N   0  0  0  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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   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
   -1.4760    0.7526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309   -0.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2460   -0.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5815   -1.4532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559   -0.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0408   -0.6995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8109    0.7526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5955    1.0075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 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
 17 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  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 16 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
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 33 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END

     RDKit          3D

 84 86  0  0  0  0  0  0  0  0999 V2000
   -4.3088   -4.8324    1.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6653   -3.5184    1.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8771   -3.3838    2.4766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9311   -2.4519    0.6573 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3449   -1.1342    0.7854 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7212   -0.7480   -0.5400 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7570    0.2345   -0.3781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4870   -0.2047   -0.6195 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0687    0.6226   -1.7980 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2340    1.9654   -1.2899 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4363    0.0991   -2.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3951    0.1034   -1.0151 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6065   -0.5571   -1.4816 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8631    0.0896   -1.6024 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9298    1.3050   -1.2891 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0750   -0.6258   -2.0810 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1754    0.2185   -2.1547 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8065   -1.3351   -3.3896 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0294   -2.0687   -3.8826 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7747   -2.7526   -5.1358 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8009   -0.6106    0.1689 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6683   -0.4660    1.2406 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4741    0.0725    0.5037 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0401   -0.2552    1.7588 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0854    0.8739    2.5633 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9710    0.7436    3.6359 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7056    1.8248    4.4414 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3608    3.1103    3.9777 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7481    2.9943    3.9389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7845    1.9563    4.4291 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4154    1.4432    5.5588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2244    1.2762    3.1599 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9027    2.2117    2.3864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6208   -0.5383   -1.5476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4299    0.5294   -1.3186 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1389    1.7071   -2.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3356    1.2804   -3.6077 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4220    0.9861    0.0973 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5575    1.7956    0.2890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4850   -0.1641    1.0783 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3656    0.3377    2.3600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5531   -5.6533    1.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8508   -4.8812    0.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0779   -4.9261    2.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5946   -2.5916   -0.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6171   -1.0374    1.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1335   -1.6708   -0.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4361   -1.2897   -0.8886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886    0.6150   -2.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6657    2.4677   -1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9240    2.4946   -1.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3895   -0.8841   -2.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8485    0.8225   -2.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6509    1.1555   -0.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5160   -1.5620   -1.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3674   -1.4217   -1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7208    0.2264   -1.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5779   -0.5446   -4.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9372   -1.9913   -3.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8169   -1.3032   -4.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4061   -2.8226   -3.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2572   -3.6521   -5.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6297   -2.9379   -5.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6651   -1.6680   -0.0942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7946   -1.3041    1.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7194    1.1743    0.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4543    1.7645    1.9841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0343    1.6209    5.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0199    3.4330    2.9945 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1098    3.8778    4.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1644    3.5330    3.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0223    3.0438    4.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3177    1.8651    5.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8157    0.3598    3.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4401    2.3866    1.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5148    0.2282   -1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9650    2.4459   -2.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1808    2.1876   -2.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5268    0.2461   -3.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1750    1.7240   -4.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5534    1.6558    0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9148    1.7358    1.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4592   -0.6545    0.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0749   -0.4022    2.9695 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5 40  1  0
 40 41  1  0
 40 38  1  0
 38 39  1  0
 38 35  1  0
 35 36  1  0
 36 37  1  0
 35 34  1  0
 34  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  1  0
 14 15  2  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
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 27 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
  6  5  1  0
 23  8  1  0
 32 25  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  4 45  1  0
  5 46  1  1
 40 83  1  1
 41 84  1  0
 38 81  1  1
 39 82  1  0
 35 76  1  6
 36 77  1  0
 36 78  1  0
 37 79  1  0
 37 80  1  0
  6 47  1  6
  8 48  1  6
  9 49  1  6
 10 50  1  0
 10 51  1  0
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 16 56  1  1
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 21 64  1  6
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 27 68  1  1
 28 69  1  0
 28 70  1  0
 29 71  1  0
 30 72  1  6
 31 73  1  0
 32 74  1  1
 33 75  1  0
M  END


  Mrv1533004191516592D          

 41 43  0  0  0  0            999 V2000
   -5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   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
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 N   0  0  0  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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   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
   -1.4760    0.7526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309   -0.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2460   -0.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5815   -1.4532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5559   -0.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0408   -0.6995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8109    0.7526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5955    1.0075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 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
 17 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  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 16 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
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 33 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0282179

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)NC1C(O)C(O)C(CN)OC1OC1C(N)CC(NC(=O)C(O)CCN)C(O)C1OC1OC(CO)C(O)C1O

> <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)

> <INCHI_KEY>
YWZWUOBLFGEYKH-UHFFFAOYSA-N

> <FORMULA>
C23H43N5O13

> <MOLECULAR_WEIGHT>
597.619

> <EXACT_MASS>
597.285736465

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
59.1411202796062

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-amino-N-(5-amino-4-{[6-(aminomethyl)-3-acetamido-4,5-dihydroxyoxan-2-yl]oxy}-3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl)-2-hydroxybutanamide

> <ALOGPS_LOGP>
-3.06

> <JCHEM_LOGP>
-8.135201129000002

> <ALOGPS_LOGS>
-0.86

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
3

> <JCHEM_PKA>
12.386589297967785

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.886264114315797

> <JCHEM_PKA_STRONGEST_BASIC>
9.745839302262807

> <JCHEM_POLAR_SURFACE_AREA>
314.79

> <JCHEM_REFRACTIVITY>
133.3223

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.24e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-amino-N-(5-amino-4-{[6-(aminomethyl)-3-acetamido-4,5-dihydroxyoxan-2-yl]oxy}-3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl)-2-hydroxybutanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -9.336   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -8.002  10.780   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      -6.668   8.470   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.668  11.550   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.001  13.090   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -1.334  13.090   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0      -2.667   9.240   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -1.334   8.470   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       8.002   4.620   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -2.755   1.405   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -3.231  -0.060   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.326  -1.306   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -2.952  -2.713   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -4.771  -0.060   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -5.676  -1.306   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -5.247   1.405   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -6.712   1.881   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   14                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13    5   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   31                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   20   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   16   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   40                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   38                                                  
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   35   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   33   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END

View in JSmol

Synonyms

Value	Source
4-Amino-N-(5-amino-4-{[6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[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

4-amino-N-(5-amino-4-{[6-(aminomethyl)-3-acetamido-4,5-dihydroxyoxan-2-yl]oxy}-3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl)-2-hydroxybutanamide

Traditional Name

4-amino-N-(5-amino-4-{[6-(aminomethyl)-3-acetamido-4,5-dihydroxyoxan-2-yl]oxy}-3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl)-2-hydroxybutanamide

CAS Registry Number

Not Available

SMILES

CC(=O)NC1C(O)C(O)C(CN)OC1OC1C(N)CC(NC(=O)C(O)CCN)C(O)C1OC1OC(CO)C(O)C1O

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)

InChI Key

YWZWUOBLFGEYKH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces fradiae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4,5-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that are glycosidically linked to a pyranose of furanose unit at the C4- and C5-positions.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

4,5-disubstituted 2-deoxystreptamines

Alternative Parents

Substituents

4,5-disubstituted 2-deoxystreptamine
N-acyl-alpha-hexosamine
Gamma amino acid or derivatives
Glycosyl compound
O-glycosyl compound
Aminocyclitol or derivatives
Cyclohexanol
Cyclohexylamine
Cyclitol or derivatives
Fatty amide
Fatty acyl
Monosaccharide
N-acyl-amine
Oxane
1,3-aminoalcohol
Cyclic alcohol
Acetamide
Tetrahydrofuran
Secondary carboxylic acid amide
Secondary alcohol
Amino acid or derivatives
Carboxamide group
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Oxacycle
Primary amine
Organonitrogen compound
Primary alcohol
Carbonyl group
Organopnictogen compound
Organic nitrogen compound
Primary aliphatic amine
Amine
Organic oxide
Hydrocarbon derivative
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	-3.1	ALOGPS
logP	-8.1	ChemAxon
logS	-0.86	ALOGPS
pKa (Strongest Acidic)	11.89	ChemAxon
pKa (Strongest Basic)	9.75	ChemAxon
Physiological Charge	3	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	314.79 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	133.32 m³·mol⁻¹	ChemAxon
Polarizability	59.14 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-amino-n-(5-amino-4-{[6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl)-2-hydroxybutanimidic acid (NP0282179)

MOL for NP0282179 (4-amino-n-(5-amino-4-{[6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl)-2-hydroxybutanimidic acid)

3D MOL for NP0282179 (4-amino-n-(5-amino-4-{[6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl)-2-hydroxybutanimidic acid)

3D SDF for NP0282179 (4-amino-n-(5-amino-4-{[6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl)-2-hydroxybutanimidic acid)

3D-SDF for NP0282179 (4-amino-n-(5-amino-4-{[6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl)-2-hydroxybutanimidic acid)

PDB for NP0282179 (4-amino-n-(5-amino-4-{[6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl)-2-hydroxybutanimidic acid)

3D PDB for NP0282179 (4-amino-n-(5-amino-4-{[6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl)-2-hydroxybutanimidic acid)

SMILES for NP0282179 (4-amino-n-(5-amino-4-{[6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl)-2-hydroxybutanimidic acid)

INCHI for NP0282179 (4-amino-n-(5-amino-4-{[6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl)-2-hydroxybutanimidic acid)

Structure for NP0282179 (4-amino-n-(5-amino-4-{[6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl)-2-hydroxybutanimidic acid)

3D Structure for NP0282179 (4-amino-n-(5-amino-4-{[6-(aminomethyl)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl)-2-hydroxybutanimidic acid)