NP-MRD: Showing NP-Card for (2r)-2-[(2r,3s,4r,5s,6r)-5-ethyl-6-[(2s,3s,4s,6r)-6-[(2s,2'r,3'r,4s,5s,5'r)-5'-ethyl-2'-hydroxy-5'-[(1s)-1-hydroxybutyl]-2,3',4-trimethyl-[2,2'-bioxolan]-5-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2,4-dihydroxy-3-methyloxan-2-yl]butanoic acid (NP0152296)

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Record Information

Version

2.0

Created at

2022-09-02 08:44:22 UTC

Updated at

2022-09-02 08:44:22 UTC

NP-MRD ID

NP0152296

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-2-[(2r,3s,4r,5s,6r)-5-ethyl-6-[(2s,3s,4s,6r)-6-[(2s,2'r,3'r,4s,5s,5'r)-5'-ethyl-2'-hydroxy-5'-[(1s)-1-hydroxybutyl]-2,3',4-trimethyl-[2,2'-bioxolan]-5-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2,4-dihydroxy-3-methyloxan-2-yl]butanoic acid

Description

Inostamycin belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. (2r)-2-[(2r,3s,4r,5s,6r)-5-ethyl-6-[(2s,3s,4s,6r)-6-[(2s,2'r,3'r,4s,5s,5'r)-5'-ethyl-2'-hydroxy-5'-[(1s)-1-hydroxybutyl]-2,3',4-trimethyl-[2,2'-bioxolan]-5-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2,4-dihydroxy-3-methyloxan-2-yl]butanoic acid was first documented in 2005 (PMID: 16235909). Based on a literature review a small amount of articles have been published on Inostamycin (PMID: 17671894) (PMID: 26800259) (PMID: 22472572) (PMID: 20070255).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022210442D          

 49 51  0  0  1  0            999 V2000
   -1.4678    0.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6608    0.8001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1088    0.1870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6982    0.3586    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9531    1.1432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2502   -0.2545    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5828   -0.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6690   -1.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8022    0.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    0.0230    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2704    0.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4697   -0.7975    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2947   -0.7975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -1.6180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3629   -1.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6914   -2.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9572   -4.2683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4269   -3.3498    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2393   -3.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5215   -2.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0841   -2.8610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4302   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8109   -2.4026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6627   -0.9690    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  6  0  0  0
  6  4  1  1  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
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 12 13  1  1  0  0  0
 12 14  1  6  0  0  0
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 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
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 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 31 29  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  1  0  0  0
 35 36  1  6  0  0  0
 36 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 33 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
 43 44  1  6  0  0  0
 43 45  1  0  0  0  0
 31 45  1  0  0  0  0
 45 46  1  6  0  0  0
 46 47  1  0  0  0  0
 19 48  1  0  0  0  0
 14 48  1  1  0  0  0
 12 49  1  0  0  0  0
  6 49  1  0  0  0  0
M  END

     RDKit          3D

117119  0  0  0  0  0  0  0  0999 V2000
   10.4891   -2.8358    0.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2649   -2.2012    0.6858 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6562   -1.1743   -0.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4408   -0.6092    0.4289 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5411   -1.6562    0.7040 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7673    0.4799   -0.3635 C   0  0  1  0  0  0  0  0  0  0  0  0
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    8.2237    2.1426    0.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2928    0.0253   -1.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7968    0.0500   -1.5845 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.4126    1.9891    1.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1244    1.3959    1.8368 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3980    0.2678    2.8520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4510    0.8403    0.6157 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1117    1.5800    0.4596 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4327    3.0423    0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7548    3.9425    0.1312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6739    1.0691   -0.6588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9099    1.9257   -1.5337 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1440   -1.3159   -0.9920 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6623   -0.1643   -0.2919 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -8.9829   -0.8048    2.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1684   -1.8952    1.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4759   -2.4895    2.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2192   -3.0377    0.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8934   -2.8430    2.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8416   -1.9252   -1.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7762   -3.4955    0.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8737   -2.9922   -1.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6543   -5.0941   -1.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1220   -4.0892   -1.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4627   -5.0014    0.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  6
  7  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  1
 12 49  1  0
 12 14  1  0
 14 15  1  6
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 48  1  0
 19 20  1  0
 20 21  1  0
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 23 24  2  0
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 27 28  1  0
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 29 30  1  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  1
 33 35  1  0
 35 36  1  0
 36 37  1  0
 35 38  1  0
 38 40  1  0
 38 39  2  0
 33 41  1  0
 41 42  1  0
 41 43  1  0
 43 44  1  0
 43 45  1  0
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 46 47  1  0
 49  6  1  0
 48 14  1  0
 45 31  1  0
  1 50  1  0
  1 51  1  0
  1 52  1  0
  2 53  1  0
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  3 55  1  0
  3 56  1  0
  4 57  1  1
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  7 59  1  0
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  8 61  1  0
  8 62  1  0
  8 63  1  0
  9 64  1  0
  9 65  1  0
 10 66  1  6
 11 67  1  0
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 13 70  1  0
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 19 80  1  1
 20 81  1  1
 21 82  1  0
 21 83  1  0
 22 84  1  0
 22 85  1  0
 22 86  1  0
 25 87  1  6
 26 88  1  0
 26 89  1  0
 26 90  1  0
 27 91  1  6
 28 92  1  0
 29 93  1  6
 30 94  1  0
 30 95  1  0
 30 96  1  0
 31 97  1  1
 34 98  1  0
 35 99  1  1
 36100  1  0
 36101  1  0
 37102  1  0
 37103  1  0
 37104  1  0
 40105  1  0
 41106  1  1
 42107  1  0
 42108  1  0
 42109  1  0
 43110  1  6
 44111  1  0
 45112  1  6
 46113  1  0
 46114  1  0
 47115  1  0
 47116  1  0
 47117  1  0
M  END


  Mrv1652309022210442D          

 49 51  0  0  1  0            999 V2000
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   -0.6608    0.8001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1088    0.1870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6982    0.3586    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9531    1.1432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2502   -0.2545    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5828   -0.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6690   -1.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8022    0.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    0.0230    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2704    0.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4697   -0.7975    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2947   -0.7975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -1.6180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3629   -1.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760   -2.4026    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6914   -2.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9572   -4.2683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4269   -3.3498    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2393   -3.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5215   -2.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8966   -2.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0841   -2.8610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1787   -1.9425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8109   -2.4026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6627   -0.9690    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  6  0  0  0
  6  4  1  1  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  6  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 31 29  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  1  0  0  0
 35 36  1  6  0  0  0
 36 37  1  0  0  0  0
 35 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 33 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
 43 44  1  6  0  0  0
 43 45  1  0  0  0  0
 31 45  1  0  0  0  0
 45 46  1  6  0  0  0
 46 47  1  0  0  0  0
 19 48  1  0  0  0  0
 14 48  1  1  0  0  0
 12 49  1  0  0  0  0
  6 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0152296

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC[C@H](O)[C@@]1(CC)C[C@@H](C)[C@@](O)(O1)[C@]1(C)C[C@H](C)[C@H](O1)[C@@H](CC)C(=O)[C@@H](C)[C@@H](O)[C@H](C)[C@H]1O[C@@](O)([C@@H](CC)C(O)=O)[C@@H](C)[C@H](O)[C@@H]1CC

> <INCHI_IDENTIFIER>
InChI=1S/C38H68O11/c1-12-17-28(39)36(16-5)19-21(7)38(46,49-36)35(11)18-20(6)32(47-35)25(13-2)30(41)22(8)29(40)23(9)33-26(14-3)31(42)24(10)37(45,48-33)27(15-4)34(43)44/h20-29,31-33,39-40,42,45-46H,12-19H2,1-11H3,(H,43,44)/t20-,21+,22-,23-,24-,25-,26-,27-,28-,29+,31-,32-,33+,35-,36+,37+,38+/m0/s1

> <INCHI_KEY>
NZJHONRWXITMMC-LPMSCSBASA-N

> <FORMULA>
C38H68O11

> <MOLECULAR_WEIGHT>
700.951

> <EXACT_MASS>
700.47616301

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
117

> <JCHEM_AVERAGE_POLARIZABILITY>
77.99432525715716

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-[(2R,3S,4R,5S,6R)-5-ethyl-6-[(2S,3S,4S,6R)-6-[(2S,2'R,3'R,4S,5S,5'R)-5'-ethyl-2'-hydroxy-5'-[(1S)-1-hydroxybutyl]-2,3',4-trimethyl-[2,2'-bioxolane]-5-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2,4-dihydroxy-3-methyloxan-2-yl]butanoic acid

> <ALOGPS_LOGP>
3.73

> <JCHEM_LOGP>
6.337238315333334

> <ALOGPS_LOGS>
-4.85

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.758086910685696

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.298298085214073

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0375672974989314

> <JCHEM_POLAR_SURFACE_AREA>
183.20999999999998

> <JCHEM_REFRACTIVITY>
184.1217000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.87e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(2R,3S,4R,5S,6R)-5-ethyl-6-[(2S,3S,4S,6R)-6-[(2S,2'R,3'R,4S,5S,5'R)-5'-ethyl-2'-hydroxy-5'-[(1S)-1-hydroxybutyl]-2,3',4-trimethyl-[2,2'-bioxolane]-5-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2,4-dihydroxy-3-methyloxan-2-yl]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.740   1.173   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.234   1.494   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.203   0.349   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.303   0.669   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.779   2.134   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.334  -0.475   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.088  -1.380   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.249  -2.912   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.364   0.669   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.771   0.043   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.105   0.813   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.610  -1.489   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.150  -1.489   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.771  -3.020   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.277  -2.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.231  -3.020   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.755  -4.485   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.291  -4.961   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      14.853  -7.967   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      13.864  -6.253   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      15.380  -5.985   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      15.907  -4.538   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      12.874  -5.073   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      11.357  -5.341   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      13.400  -3.626   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       5.247  -4.485   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       3.104  -1.809   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    9   49                                             
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   49                                             
CONECT   13   12                                                            
CONECT   14   12   15   16   48                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   48                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   45                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35   41                                             
CONECT   34   33                                                            
CONECT   35   33   36   38                                                  
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   35   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   33   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   31   46                                                  
CONECT   46   45   47                                                       
CONECT   47   46                                                            
CONECT   48   19   14                                                       
CONECT   49   12    6                                                       
MASTER        0    0    0    0    0    0    0    0   49    0  102    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₈H₆₈O₁₁

Average Mass

700.9510 Da

Monoisotopic Mass

700.47616 Da

IUPAC Name

(2R)-2-[(2R,3S,4R,5S,6R)-5-ethyl-6-[(2S,3S,4S,6R)-6-[(2S,2'R,3'R,4S,5S,5'R)-5'-ethyl-2'-hydroxy-5'-[(1S)-1-hydroxybutyl]-2,3',4-trimethyl-[2,2'-bioxolane]-5-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2,4-dihydroxy-3-methyloxan-2-yl]butanoic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CCC[C@H](O)[C@@]1(CC)C[C@@H](C)[C@@](O)(O1)[C@]1(C)C[C@H](C)[C@H](O1)[C@@H](CC)C(=O)[C@@H](C)[C@@H](O)[C@H](C)[C@H]1O[C@@](O)([C@@H](CC)C(O)=O)[C@@H](C)[C@H](O)[C@@H]1CC

InChI Identifier

InChI=1S/C38H68O11/c1-12-17-28(39)36(16-5)19-21(7)38(46,49-36)35(11)18-20(6)32(47-35)25(13-2)30(41)22(8)29(40)23(9)33-26(14-3)31(42)24(10)37(45,48-33)27(15-4)34(43)44/h20-29,31-33,39-40,42,45-46H,12-19H2,1-11H3,(H,43,44)/t20-,21+,22-,23-,24-,25-,26-,27-,28-,29+,31-,32-,33+,35-,36+,37+,38+/m0/s1

InChI Key

NZJHONRWXITMMC-LPMSCSBASA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Sesterterpenoids

Alternative Parents

Substituents

Sesterterpenoid
Terpene glycoside
Hydroxy fatty acid
Heterocyclic fatty acid
Branched fatty acid
Fatty acyl
Fatty acid
Oxane
Beta-hydroxy ketone
Tetrahydrofuran
Secondary alcohol
Ketone
Hemiacetal
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	3.73	ALOGPS
logP	6.34	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.21 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	184.12 m³·mol⁻¹	ChemAxon
Polarizability	77.99 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

C00016660

Chemspider ID

103884833

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

124081057

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fang J, Nakamura H, Iyer AK: Tumor-targeted induction of oxystress for cancer therapy. J Drug Target. 2007 Aug-Sep;15(7-8):475-86. doi: 10.1080/10611860701498286. [PubMed:17671894 ]
Yu G, Jung B, Lee HS, Kang SH: The Total Synthesis of Inostamycin A. Angew Chem Int Ed Engl. 2016 Feb 12;55(7):2573-6. doi: 10.1002/anie.201510852. Epub 2016 Jan 22. [PubMed:26800259 ]
Yamamoto K, Makino M, Watanapokasin R, Tashiro E, Imoto M: Inostamycin enhanced TRAIL-induced apoptosis through DR5 upregulation on the cell surface. J Antibiot (Tokyo). 2012 Jun;65(6):295-300. doi: 10.1038/ja.2012.21. Epub 2012 Apr 4. [PubMed:22472572 ]
Baba Y, Kato Y, Ogawa K: Inostamycin prevents malignant phenotype of cancer: inhibition of phosphatidylinositol synthesis provides a therapeutic advantage for head and neck squamous cell carcinoma. Cell Biol Int. 2010 Feb;34(2):171-5. doi: 10.1042/CBI20090310. [PubMed:20070255 ]
Fuller NO, Morken JP: Studies on the synthesis of the inostamycin natural products: a reductive aldol/reductive Claisen approach to the C10-C24 ketone fragment. Org Lett. 2005 Oct 27;7(22):4867-9. doi: 10.1021/ol0516115. [PubMed:16235909 ]
LOTUS database [Link]

Showing NP-Card for (2r)-2-[(2r,3s,4r,5s,6r)-5-ethyl-6-[(2s,3s,4s,6r)-6-[(2s,2'r,3'r,4s,5s,5'r)-5'-ethyl-2'-hydroxy-5'-[(1s)-1-hydroxybutyl]-2,3',4-trimethyl-[2,2'-bioxolan]-5-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2,4-dihydroxy-3-methyloxan-2-yl]butanoic acid (NP0152296)

MOL for NP0152296 ((2r)-2-[(2r,3s,4r,5s,6r)-5-ethyl-6-[(2s,3s,4s,6r)-6-[(2s,2'r,3'r,4s,5s,5'r)-5'-ethyl-2'-hydroxy-5'-[(1s)-1-hydroxybutyl]-2,3',4-trimethyl-[2,2'-bioxolan]-5-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2,4-dihydroxy-3-methyloxan-2-yl]butanoic acid)

3D MOL for NP0152296 ((2r)-2-[(2r,3s,4r,5s,6r)-5-ethyl-6-[(2s,3s,4s,6r)-6-[(2s,2'r,3'r,4s,5s,5'r)-5'-ethyl-2'-hydroxy-5'-[(1s)-1-hydroxybutyl]-2,3',4-trimethyl-[2,2'-bioxolan]-5-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2,4-dihydroxy-3-methyloxan-2-yl]butanoic acid)

3D SDF for NP0152296 ((2r)-2-[(2r,3s,4r,5s,6r)-5-ethyl-6-[(2s,3s,4s,6r)-6-[(2s,2'r,3'r,4s,5s,5'r)-5'-ethyl-2'-hydroxy-5'-[(1s)-1-hydroxybutyl]-2,3',4-trimethyl-[2,2'-bioxolan]-5-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2,4-dihydroxy-3-methyloxan-2-yl]butanoic acid)

3D-SDF for NP0152296 ((2r)-2-[(2r,3s,4r,5s,6r)-5-ethyl-6-[(2s,3s,4s,6r)-6-[(2s,2'r,3'r,4s,5s,5'r)-5'-ethyl-2'-hydroxy-5'-[(1s)-1-hydroxybutyl]-2,3',4-trimethyl-[2,2'-bioxolan]-5-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2,4-dihydroxy-3-methyloxan-2-yl]butanoic acid)

PDB for NP0152296 ((2r)-2-[(2r,3s,4r,5s,6r)-5-ethyl-6-[(2s,3s,4s,6r)-6-[(2s,2'r,3'r,4s,5s,5'r)-5'-ethyl-2'-hydroxy-5'-[(1s)-1-hydroxybutyl]-2,3',4-trimethyl-[2,2'-bioxolan]-5-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2,4-dihydroxy-3-methyloxan-2-yl]butanoic acid)

3D PDB for NP0152296 ((2r)-2-[(2r,3s,4r,5s,6r)-5-ethyl-6-[(2s,3s,4s,6r)-6-[(2s,2'r,3'r,4s,5s,5'r)-5'-ethyl-2'-hydroxy-5'-[(1s)-1-hydroxybutyl]-2,3',4-trimethyl-[2,2'-bioxolan]-5-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2,4-dihydroxy-3-methyloxan-2-yl]butanoic acid)

SMILES for NP0152296 ((2r)-2-[(2r,3s,4r,5s,6r)-5-ethyl-6-[(2s,3s,4s,6r)-6-[(2s,2'r,3'r,4s,5s,5'r)-5'-ethyl-2'-hydroxy-5'-[(1s)-1-hydroxybutyl]-2,3',4-trimethyl-[2,2'-bioxolan]-5-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2,4-dihydroxy-3-methyloxan-2-yl]butanoic acid)

INCHI for NP0152296 ((2r)-2-[(2r,3s,4r,5s,6r)-5-ethyl-6-[(2s,3s,4s,6r)-6-[(2s,2'r,3'r,4s,5s,5'r)-5'-ethyl-2'-hydroxy-5'-[(1s)-1-hydroxybutyl]-2,3',4-trimethyl-[2,2'-bioxolan]-5-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2,4-dihydroxy-3-methyloxan-2-yl]butanoic acid)

Structure for NP0152296 ((2r)-2-[(2r,3s,4r,5s,6r)-5-ethyl-6-[(2s,3s,4s,6r)-6-[(2s,2'r,3'r,4s,5s,5'r)-5'-ethyl-2'-hydroxy-5'-[(1s)-1-hydroxybutyl]-2,3',4-trimethyl-[2,2'-bioxolan]-5-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2,4-dihydroxy-3-methyloxan-2-yl]butanoic acid)

3D Structure for NP0152296 ((2r)-2-[(2r,3s,4r,5s,6r)-5-ethyl-6-[(2s,3s,4s,6r)-6-[(2s,2'r,3'r,4s,5s,5'r)-5'-ethyl-2'-hydroxy-5'-[(1s)-1-hydroxybutyl]-2,3',4-trimethyl-[2,2'-bioxolan]-5-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-2,4-dihydroxy-3-methyloxan-2-yl]butanoic acid)