NP-MRD: Showing NP-Card for 6'-Deamino-6'-hydroxybutirosin A (NP0062003)

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Record Information

Version

2.0

Created at

2022-04-28 06:41:28 UTC

Updated at

2022-04-28 06:41:28 UTC

NP-MRD ID

NP0062003

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6'-Deamino-6'-hydroxybutirosin A

Description

(2R)-4-amino-N-[(1R,2R,3S,4S,5R)-5-amino-4-{[(2S,3R,4R,5S,6S)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl]-2-hydroxybutanimidic acid belongs to the class of organic compounds known as aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines. 6'-Deamino-6'-hydroxybutirosin A is found in Bacillus circulans strain No. YQW-B6. Based on a literature review very few articles have been published on (2R)-4-amino-N-[(1R,2R,3S,4S,5R)-5-amino-4-{[(2S,3R,4R,5S,6S)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-hydroxycyclohexyl]-2-hydroxybutanimidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282208412D          

 38 40  0  0  1  0            999 V2000
    3.5724   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  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   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4760    0.8974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7309    1.6820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2460    2.3495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    1.6820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0408    2.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7053    3.1032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8109    0.8974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6914    0.6425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    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
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  1  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   -2.8875    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
    5.0013   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  5  8  1  6  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
  9 16  1  0  0  0  0
 10 17  1  1  0  0  0
  4 18  1  1  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  6  0  0  0
 25 26  1  0  0  0  0
 22 27  1  6  0  0  0
 21 28  1  1  0  0  0
 20 29  1  6  0  0  0
  3 30  1  6  0  0  0
  1 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 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
 34 38  1  6  0  0  0
M  END

     RDKit          3D

 78 80  0  0  0  0  0  0  0  0999 V2000
    8.2417   -0.2402    0.3773 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7253   -1.5424    0.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2360   -1.3455    1.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6090   -2.6416    1.4878 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1435   -3.0920    2.6857 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1624   -2.3895    1.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6083   -2.5805    2.8151 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3857   -1.9253    0.6388 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9445   -1.6430    0.7396 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2534   -2.5996   -0.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2737   -1.9579   -1.0868 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5460   -2.9138   -1.7535 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5067   -0.9525   -0.2636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6466   -0.6276   -0.9478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8231   -0.9772   -0.2465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5245    0.2084   -0.0729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7658    0.0734    0.4870 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8099    0.8503   -0.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4950    2.2042   -0.3479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2193   -1.3667    0.5903 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5776   -1.3388    0.9076 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.4934   -3.3614   -0.6264 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4417   -1.7748   -2.4937 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369    0.2121   -0.0704 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1858    1.2042    0.6656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3389    2.3616   -0.0486 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3723    3.4029    0.5772 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0475    4.4772   -0.2490 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4289    5.8063    0.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0500    6.7953   -0.5631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4417    4.3842   -0.4891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6380    4.5700   -1.8707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7185    2.9218   -0.1123 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4074    2.8578    1.0854 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7635   -0.2035    0.4884 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8370    0.2972   -0.2799 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1295   -0.2288   -0.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1829   -0.0477    0.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2448   -1.8512    1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9270   -2.2843    0.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0606   -0.5260    1.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8041   -1.1320    0.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7731   -3.3772    0.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1729   -4.0888    2.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8049   -1.7540   -0.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6854   -1.8865    1.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6794   -3.3597    0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9578   -3.2182   -0.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8906   -1.3812   -1.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1081   -3.8531   -1.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6754   -2.6322   -2.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8036   -0.9505   -2.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1062   -2.6449   -2.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6405    0.6309   -1.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0578    2.3079   -1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6119    4.3272   -1.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5099    5.9134    0.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1504    6.0157    1.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2372    7.6306   -0.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0324    5.0813    0.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8185    4.9387   -2.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6018    1.2641   -0.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0
  3  4  1  0
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 37  9  1  0
 24 15  1  0
 35 28  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  2 42  1  0
  3 43  1  0
  3 44  1  0
  4 45  1  6
  5 46  1  0
  8 47  1  0
  9 48  1  1
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 10 50  1  0
 11 51  1  6
 12 52  1  0
 12 53  1  0
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 15 55  1  1
 17 56  1  1
 18 57  1  0
 18 58  1  0
 19 59  1  0
 20 60  1  1
 21 61  1  0
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 23 63  1  0
 24 64  1  6
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 25 66  1  0
 26 67  1  6
 28 68  1  6
 30 69  1  6
 31 70  1  0
 31 71  1  0
 32 72  1  0
 33 73  1  1
 34 74  1  0
 35 75  1  6
 36 76  1  0
 37 77  1  1
 38 78  1  0
M  END


  Mrv1652304282208412D          

 38 40  0  0  1  0            999 V2000
    3.5724   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  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   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4760    0.8974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7309    1.6820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2460    2.3495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    1.6820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0408    2.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7053    3.1032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8109    0.8974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6914    0.6425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    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
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  1  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   -2.8875    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
    5.0013   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  5  8  1  6  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
  9 16  1  0  0  0  0
 10 17  1  1  0  0  0
  4 18  1  1  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  6  0  0  0
 25 26  1  0  0  0  0
 22 27  1  6  0  0  0
 21 28  1  1  0  0  0
 20 29  1  6  0  0  0
  3 30  1  6  0  0  0
  1 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 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
 34 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0062003

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H40N4O13/c22-2-1-8(28)19(34)25-7-3-6(23)17(37-20-11(24)15(32)13(30)9(4-26)35-20)18(12(7)29)38-21-16(33)14(31)10(5-27)36-21/h6-18,20-21,26-33H,1-5,22-24H2,(H,25,34)/t6-,7-,8-,9+,10-,11-,12-,13-,14-,15-,16+,17+,18+,20-,21+/m1/s1

> <INCHI_KEY>
NRBAPKVHONIXPV-CVDWYIPCSA-N

> <FORMULA>
C21H40N4O13

> <MOLECULAR_WEIGHT>
556.566

> <EXACT_MASS>
556.259187364

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
54.04283161202868

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-3.23

> <JCHEM_LOGP>
-7.847165935333334

> <ALOGPS_LOGS>
-0.77

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
3

> <JCHEM_PKA>
12.72216155658661

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.11321451291182

> <JCHEM_PKA_STRONGEST_BASIC>
9.706942917027257

> <JCHEM_POLAR_SURFACE_AREA>
305.92

> <JCHEM_REFRACTIVITY>
122.22099999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.55e+01 g/l

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

> <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       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.755   1.675   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.231   3.140   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.326   4.386   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.771   3.140   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.676   4.386   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.050   5.793   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.247   1.675   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.291   1.199   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.669   3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.336   0.770   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.003   0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      13.337   1.540   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      12.003   3.850   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       9.336   5.390   0.000  0.00  0.00           O+0
HETATM   29  N   UNK     0       6.668   3.850   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0       9.336  -0.770   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0       6.668  -5.390   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0      13.337  -6.160   0.000  0.00  0.00           N+0
HETATM   38  O   UNK     0       9.336  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2    6   31                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13    9                                                       
CONECT   17   10                                                            
CONECT   18    4   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   29                                                  
CONECT   21   20   22   28                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   19                                                       
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27   22                                                            
CONECT   28   21                                                            
CONECT   29   20                                                            
CONECT   30    3                                                            
CONECT   31    1   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   38                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   34                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₂₁H₄₀N₄O₁₃

Average Mass

556.5660 Da

Monoisotopic Mass

556.25919 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

NCC[C@@H](O)C(=O)N[C@@H]1C[C@@H](N)[C@H](O[C@H]2O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]2N)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)[C@@H]1O

InChI Identifier

InChI=1S/C21H40N4O13/c22-2-1-8(28)19(34)25-7-3-6(23)17(37-20-11(24)15(32)13(30)9(4-26)35-20)18(12(7)29)38-21-16(33)14(31)10(5-27)36-21/h6-18,20-21,26-33H,1-5,22-24H2,(H,25,34)/t6-,7-,8-,9+,10-,11-,12-,13-,14-,15-,16+,17+,18+,20-,21+/m1/s1

InChI Key

NRBAPKVHONIXPV-CVDWYIPCSA-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
Bacillus circulans strain No. YQW-B6	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidically linked to a carbohydrate moiety. There are two major classes of aminoglycosides containing a 2-streptamine core. They are called 4,5- and 4,6-disubstituted 2-deoxystreptamines.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Aminocyclitol glycosides

Alternative Parents

Substituents

Amino cyclitol glycoside
O-glycosyl compound
Glycosyl compound
Aminocyclitol or derivatives
Cyclohexylamine
Cyclohexanol
Oxane
Monosaccharide
Cyclitol or derivatives
Tetrahydrofuran
Cyclic alcohol
1,3-aminoalcohol
Secondary alcohol
1,2-aminoalcohol
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid derivative
Carboximidic acid
Acetal
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Primary alcohol
Organonitrogen compound
Primary aliphatic amine
Amine
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	-3.2	ALOGPS
logP	-7.8	ChemAxon
logS	-0.77	ALOGPS
pKa (Strongest Acidic)	12.11	ChemAxon
pKa (Strongest Basic)	9.71	ChemAxon
Physiological Charge	3	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	305.92 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	122.22 m³·mol⁻¹	ChemAxon
Polarizability	54.04 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

162978543

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 6'-Deamino-6'-hydroxybutirosin A (NP0062003)

MOL for NP0062003 (6'-Deamino-6'-hydroxybutirosin A)

3D MOL for NP0062003 (6'-Deamino-6'-hydroxybutirosin A)

3D SDF for NP0062003 (6'-Deamino-6'-hydroxybutirosin A)

3D-SDF for NP0062003 (6'-Deamino-6'-hydroxybutirosin A)

PDB for NP0062003 (6'-Deamino-6'-hydroxybutirosin A)

3D PDB for NP0062003 (6'-Deamino-6'-hydroxybutirosin A)

SMILES for NP0062003 (6'-Deamino-6'-hydroxybutirosin A)

INCHI for NP0062003 (6'-Deamino-6'-hydroxybutirosin A)

Structure for NP0062003 (6'-Deamino-6'-hydroxybutirosin A)

3D Structure for NP0062003 (6'-Deamino-6'-hydroxybutirosin A)