NP-MRD: Showing NP-Card for TMC-89B (NP0003558)

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Record Information

Version

1.0

Created at

2020-12-09 00:46:36 UTC

Updated at

2021-07-15 16:46:44 UTC

NP-MRD ID

NP0003558

Secondary Accession Numbers

None

Natural Product Identification

Common Name

TMC-89B

Provided By

NPAtlas

Description

(2S)-N'-[(1S)-2-hydroxy-1-{[(1S)-2-hydroxy-1-({1-[2-(hydroxymethyl)oxiran-2-yl]-4-methyl-1-oxopentan-2-yl}-C-hydroxycarbonimidoyl)propyl]-C-hydroxycarbonimidoyl}propyl]-2-methylpropanediimidic acid belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. TMC-89B is found in Streptomyces sp. and Streptomyces sp. TC 1087. It was first documented in 2000 (PMID: 11099231). Based on a literature review very few articles have been published on (2S)-N'-[(1S)-2-hydroxy-1-{[(1S)-2-hydroxy-1-({1-[2-(hydroxymethyl)oxiran-2-yl]-4-methyl-1-oxopentan-2-yl}-C-hydroxycarbonimidoyl)propyl]-C-hydroxycarbonimidoyl}propyl]-2-methylpropanediimidic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117483D          

 70 70  0  0  0  0            999 V2000
   -6.4330   -0.5309   -0.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5459    0.6677   -0.8894 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3639    1.8369   -0.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3009    0.5947   -0.0886 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2805   -0.4529   -0.4631 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2042   -0.2397    0.5399 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9930    0.3692    0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8168    0.7460   -1.0262 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0913    0.5969    1.1640 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2215    1.2727    0.5469 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4952    0.6925    0.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6171   -0.4429    1.1222 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7280    1.2685   -0.0303 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8783    0.4159    0.2193 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9919    0.8042    0.9798 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0106    1.9475    1.4817 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1624   -0.0710    1.2305 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2477    0.6547    2.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7080   -1.2035    2.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6905   -2.0961    1.6261 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2133   -1.4224    3.2034 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5769    1.5858   -1.4868 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3911    0.3959   -2.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4699    2.4098   -1.6500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3925    1.5730    2.2446 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8712    2.7985    1.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4638    0.9956    2.8993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8097   -1.7963   -0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9546   -2.1824    0.9681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2005   -2.7841   -1.2577 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9393   -2.4476   -2.6980 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6475   -3.6364   -3.4155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9883   -4.2293   -0.8818 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2558   -3.6483   -0.9551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2685   -1.1979   -0.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5307   -0.2196   -0.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4079   -1.0195   -1.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3582    1.0052   -1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6688    2.6908   -0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6955    1.5160    0.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2291    2.0841   -0.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8200    1.6234   -0.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6247    0.4535    0.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8702   -0.2678   -1.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3814   -0.5644    1.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4252   -0.3570    1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0562    2.1900    0.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9222    2.2253    0.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8679   -0.5361   -0.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6149   -0.4567    0.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0909    0.6058    3.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1961    0.1094    1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3399    1.7004    1.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8831   -2.2687    2.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7382   -2.5602    0.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4586    2.2110   -1.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2389    0.4061   -3.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3383   -0.5690   -1.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4626    0.4818   -3.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8976    2.1396   -2.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3858    1.7748    2.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8959    3.0795    1.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0010    2.6016    0.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1730    3.6548    1.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1243    0.2031    3.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0242   -1.8235   -2.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7945   -2.0104   -3.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6975   -3.8663   -3.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7266   -4.9881   -1.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6571   -4.4933    0.1278 H   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
  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
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
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 14 15  1  0  0  0  0
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 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  9 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  2  0  0  0  0
 30 28  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 30  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  2 38  1  6  0  0  0
  3 39  1  0  0  0  0
  3 40  1  0  0  0  0
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  4 42  1  0  0  0  0
  4 43  1  0  0  0  0
  5 44  1  6  0  0  0
  6 45  1  0  0  0  0
  9 46  1  1  0  0  0
 10 47  1  0  0  0  0
 13 48  1  1  0  0  0
 14 49  1  0  0  0  0
 17 50  1  6  0  0  0
 18 51  1  0  0  0  0
 18 52  1  0  0  0  0
 18 53  1  0  0  0  0
 20 54  1  0  0  0  0
 20 55  1  0  0  0  0
 22 56  1  6  0  0  0
 23 57  1  0  0  0  0
 23 58  1  0  0  0  0
 23 59  1  0  0  0  0
 24 60  1  0  0  0  0
 25 61  1  1  0  0  0
 26 62  1  0  0  0  0
 26 63  1  0  0  0  0
 26 64  1  0  0  0  0
 27 65  1  0  0  0  0
 31 66  1  0  0  0  0
 31 67  1  0  0  0  0
 32 68  1  0  0  0  0
 33 69  1  0  0  0  0
 33 70  1  0  0  0  0
M  END

     RDKit          3D

 70 70  0  0  0  0  0  0  0  0999 V2000
   -6.4330   -0.5309   -0.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5459    0.6677   -0.8894 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3639    1.8369   -0.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3009    0.5947   -0.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2805   -0.4529   -0.4631 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2042   -0.2397    0.5399 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9930    0.3692    0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8168    0.7460   -1.0262 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0913    0.5969    1.1640 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2215    1.2727    0.5469 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4952    0.6925    0.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6171   -0.4429    1.1222 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7280    1.2685   -0.0303 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8783    0.4159    0.2193 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9919    0.8042    0.9798 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0106    1.9475    1.4817 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1624   -0.0710    1.2305 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2477    0.6547    2.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7080   -1.2035    2.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6905   -2.0961    1.6261 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2133   -1.4224    3.2034 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5769    1.5858   -1.4868 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3911    0.3959   -2.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4699    2.4098   -1.6500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3925    1.5730    2.2446 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8712    2.7985    1.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4638    0.9956    2.8993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8097   -1.7963   -0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9546   -2.1824    0.9681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2005   -2.7841   -1.2577 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9393   -2.4476   -2.6980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6475   -3.6364   -3.4155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9883   -4.2293   -0.8818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2558   -3.6483   -0.9551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2685   -1.1979   -0.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5307   -0.2196   -0.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4079   -1.0195   -1.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3582    1.0052   -1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6688    2.6908   -0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6955    1.5160    0.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2291    2.0841   -0.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8200    1.6234   -0.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6247    0.4535    0.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3814   -0.5644    1.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4252   -0.3570    1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0562    2.1900    0.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9222    2.2253    0.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7266   -4.9881   -1.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6571   -4.4933    0.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
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 31 66  1  0
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 33 69  1  0
 33 70  1  0
M  END


  Mrv1652306242117483D          

 70 70  0  0  0  0            999 V2000
   -6.4330   -0.5309   -0.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5459    0.6677   -0.8894 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3639    1.8369   -0.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3009    0.5947   -0.0886 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2805   -0.4529   -0.4631 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2042   -0.2397    0.5399 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9930    0.3692    0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8168    0.7460   -1.0262 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0913    0.5969    1.1640 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2215    1.2727    0.5469 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4952    0.6925    0.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6171   -0.4429    1.1222 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7280    1.2685   -0.0303 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8783    0.4159    0.2193 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9919    0.8042    0.9798 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0106    1.9475    1.4817 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1624   -0.0710    1.2305 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2477    0.6547    2.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7080   -1.2035    2.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6905   -2.0961    1.6261 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2133   -1.4224    3.2034 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5769    1.5858   -1.4868 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3911    0.3959   -2.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4699    2.4098   -1.6500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3925    1.5730    2.2446 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8712    2.7985    1.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4638    0.9956    2.8993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8097   -1.7963   -0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9546   -2.1824    0.9681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2005   -2.7841   -1.2577 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9393   -2.4476   -2.6980 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6475   -3.6364   -3.4155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9883   -4.2293   -0.8818 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2558   -3.6483   -0.9551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2685   -1.1979   -0.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5307   -0.2196   -0.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4079   -1.0195   -1.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3582    1.0052   -1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6688    2.6908   -0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6955    1.5160    0.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2291    2.0841   -0.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8200    1.6234   -0.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6247    0.4535    0.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8702   -0.2678   -1.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3814   -0.5644    1.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4252   -0.3570    1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0562    2.1900    0.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9222    2.2253    0.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8679   -0.5361   -0.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6149   -0.4567    0.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0909    0.6058    3.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1961    0.1094    1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3399    1.7004    1.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8831   -2.2687    2.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7382   -2.5602    0.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4586    2.2110   -1.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2389    0.4061   -3.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3383   -0.5690   -1.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4626    0.4818   -3.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8976    2.1396   -2.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3858    1.7748    2.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8959    3.0795    1.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0010    2.6016    0.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1730    3.6548    1.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1243    0.2031    3.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0242   -1.8235   -2.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7945   -2.0104   -3.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6975   -3.8663   -3.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7266   -4.9881   -1.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6571   -4.4933    0.1278 H   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
  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
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 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
 19 21  2  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  9 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  2  0  0  0  0
 30 28  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 30  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  2 38  1  6  0  0  0
  3 39  1  0  0  0  0
  3 40  1  0  0  0  0
  3 41  1  0  0  0  0
  4 42  1  0  0  0  0
  4 43  1  0  0  0  0
  5 44  1  6  0  0  0
  6 45  1  0  0  0  0
  9 46  1  1  0  0  0
 10 47  1  0  0  0  0
 13 48  1  1  0  0  0
 14 49  1  0  0  0  0
 17 50  1  6  0  0  0
 18 51  1  0  0  0  0
 18 52  1  0  0  0  0
 18 53  1  0  0  0  0
 20 54  1  0  0  0  0
 20 55  1  0  0  0  0
 22 56  1  6  0  0  0
 23 57  1  0  0  0  0
 23 58  1  0  0  0  0
 23 59  1  0  0  0  0
 24 60  1  0  0  0  0
 25 61  1  1  0  0  0
 26 62  1  0  0  0  0
 26 63  1  0  0  0  0
 26 64  1  0  0  0  0
 27 65  1  0  0  0  0
 31 66  1  0  0  0  0
 31 67  1  0  0  0  0
 32 68  1  0  0  0  0
 33 69  1  0  0  0  0
 33 70  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003558

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@]1(OC1([H])[H])C(=O)[C@]([H])(N([H])C(=O)[C@@]([H])(N([H])C(=O)[C@@]([H])(N([H])C(=O)[C@]([H])(C(=O)N([H])[H])C([H])([H])[H])[C@]([H])(O[H])C([H])([H])[H])[C@]([H])(O[H])C([H])([H])[H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H36N4O9/c1-9(2)6-13(16(29)21(7-26)8-34-21)23-19(32)14(11(4)27)25-20(33)15(12(5)28)24-18(31)10(3)17(22)30/h9-15,26-28H,6-8H2,1-5H3,(H2,22,30)(H,23,32)(H,24,31)(H,25,33)/t10-,11+,12+,13+,14-,15-,21+/m0/s1

> <INCHI_KEY>
SCVCWUHUBWSKHS-VQSWLDGRSA-N

> <FORMULA>
C21H36N4O9

> <MOLECULAR_WEIGHT>
488.538

> <EXACT_MASS>
488.248228755

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
49.30947661213281

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-N'-[(1S,2R)-2-hydroxy-1-{[(1S,2R)-2-hydroxy-1-{[(2R)-1-[(2R)-2-(hydroxymethyl)oxiran-2-yl]-4-methyl-1-oxopentan-2-yl]carbamoyl}propyl]carbamoyl}propyl]-2-methylpropanediamide

> <ALOGPS_LOGP>
-1.25

> <JCHEM_LOGP>
-2.629399079333334

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.984677018210505

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.46547114608772

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9371028228975806

> <JCHEM_POLAR_SURFACE_AREA>
220.67999999999998

> <JCHEM_REFRACTIVITY>
116.9131

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-N'-[(1S,2R)-2-hydroxy-1-{[(1S,2R)-2-hydroxy-1-{[(2R)-1-[(2R)-2-(hydroxymethyl)oxiran-2-yl]-4-methyl-1-oxopentan-2-yl]carbamoyl}propyl]carbamoyl}propyl]-2-methylpropanediamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 70 70  0  0  0  0  0  0  0  0999 V2000
   -6.4330   -0.5309   -0.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5459    0.6677   -0.8894 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3639    1.8369   -0.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3009    0.5947   -0.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2805   -0.4529   -0.4631 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2042   -0.2397    0.5399 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9930    0.3692    0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8168    0.7460   -1.0262 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0913    0.5969    1.1640 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2215    1.2727    0.5469 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4952    0.6925    0.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6171   -0.4429    1.1222 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7280    1.2685   -0.0303 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8783    0.4159    0.2193 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9919    0.8042    0.9798 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0106    1.9475    1.4817 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1624   -0.0710    1.2305 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2477    0.6547    2.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7080   -1.2035    2.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6905   -2.0961    1.6261 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2133   -1.4224    3.2034 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5769    1.5858   -1.4868 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3911    0.3959   -2.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4699    2.4098   -1.6500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3925    1.5730    2.2446 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8712    2.7985    1.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4638    0.9956    2.8993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8097   -1.7963   -0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9546   -2.1824    0.9681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2005   -2.7841   -1.2577 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9393   -2.4476   -2.6980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6475   -3.6364   -3.4155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9883   -4.2293   -0.8818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2558   -3.6483   -0.9551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2685   -1.1979   -0.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5307   -0.2196   -0.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4079   -1.0195   -1.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3582    1.0052   -1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6688    2.6908   -0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6955    1.5160    0.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2291    2.0841   -0.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8200    1.6234   -0.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6247    0.4535    0.9920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8702   -0.2678   -1.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3814   -0.5644    1.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4252   -0.3570    1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0562    2.1900    0.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9222    2.2253    0.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8679   -0.5361   -0.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6149   -0.4567    0.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0909    0.6058    3.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1961    0.1094    1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3399    1.7004    1.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8831   -2.2687    2.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7382   -2.5602    0.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4586    2.2110   -1.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2389    0.4061   -3.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3383   -0.5690   -1.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4626    0.4818   -3.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8976    2.1396   -2.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3858    1.7748    2.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8959    3.0795    1.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0010    2.6016    0.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1730    3.6548    1.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1243    0.2031    3.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0242   -1.8235   -2.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7945   -2.0104   -3.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6975   -3.8663   -3.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7266   -4.9881   -1.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6571   -4.4933    0.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 13 22  1  0
 22 23  1  0
 22 24  1  0
  9 25  1  0
 25 26  1  0
 25 27  1  0
  5 28  1  0
 28 29  2  0
 30 28  1  1
 30 31  1  0
 31 32  1  0
 30 33  1  0
 33 34  1  0
 34 30  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  6
  3 39  1  0
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  5 44  1  6
  6 45  1  0
  9 46  1  1
 10 47  1  0
 13 48  1  1
 14 49  1  0
 17 50  1  6
 18 51  1  0
 18 52  1  0
 18 53  1  0
 20 54  1  0
 20 55  1  0
 22 56  1  6
 23 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
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 26 62  1  0
 26 63  1  0
 26 64  1  0
 27 65  1  0
 31 66  1  0
 31 67  1  0
 32 68  1  0
 33 69  1  0
 33 70  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -6.433  -0.531  -0.883  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.546   0.668  -0.889  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.364   1.837  -0.302  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.301   0.595  -0.089  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.281  -0.453  -0.463  0.00  0.00           C+0
HETATM    6  N   UNK     0      -2.204  -0.240   0.540  0.00  0.00           N+0
HETATM    7  C   UNK     0      -0.993   0.369   0.193  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.817   0.746  -1.026  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.091   0.597   1.164  0.00  0.00           C+0
HETATM   10  N   UNK     0       1.222   1.273   0.547  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.495   0.693   0.555  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.617  -0.443   1.122  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.728   1.268  -0.030  0.00  0.00           C+0
HETATM   14  N   UNK     0       4.878   0.416   0.219  0.00  0.00           N+0
HETATM   15  C   UNK     0       5.992   0.804   0.980  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.011   1.948   1.482  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.162  -0.071   1.230  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.248   0.655   2.001  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.708  -1.204   2.062  0.00  0.00           C+0
HETATM   20  N   UNK     0       5.691  -2.096   1.626  0.00  0.00           N+0
HETATM   21  O   UNK     0       7.213  -1.422   3.203  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.577   1.586  -1.487  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.391   0.396  -2.374  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.470   2.410  -1.650  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.393   1.573   2.245  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.871   2.799   1.496  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.464   0.996   2.899  0.00  0.00           O+0
HETATM   28  C   UNK     0      -3.810  -1.796  -0.201  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.955  -2.182   0.968  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.200  -2.784  -1.258  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.939  -2.448  -2.698  0.00  0.00           C+0
HETATM   32  O   UNK     0      -3.648  -3.636  -3.416  0.00  0.00           O+0
HETATM   33  C   UNK     0      -3.988  -4.229  -0.882  0.00  0.00           C+0
HETATM   34  O   UNK     0      -5.256  -3.648  -0.955  0.00  0.00           O+0
HETATM   35  H   UNK     0      -6.269  -1.198  -0.028  0.00  0.00           H+0
HETATM   36  H   UNK     0      -7.531  -0.220  -0.764  0.00  0.00           H+0
HETATM   37  H   UNK     0      -6.408  -1.020  -1.877  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.358   1.005  -1.946  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.669   2.691  -0.148  0.00  0.00           H+0
HETATM   40  H   UNK     0      -6.696   1.516   0.710  0.00  0.00           H+0
HETATM   41  H   UNK     0      -7.229   2.084  -0.918  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.820   1.623  -0.154  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.625   0.454   0.992  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.870  -0.268  -1.458  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.381  -0.564   1.504  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.425  -0.357   1.591  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.056   2.190   0.107  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.922   2.225   0.496  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.868  -0.536  -0.196  0.00  0.00           H+0
HETATM   50  H   UNK     0       7.615  -0.457   0.308  0.00  0.00           H+0
HETATM   51  H   UNK     0       8.091   0.606   3.096  0.00  0.00           H+0
HETATM   52  H   UNK     0       9.196   0.109   1.802  0.00  0.00           H+0
HETATM   53  H   UNK     0       8.340   1.700   1.619  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.883  -2.269   2.261  0.00  0.00           H+0
HETATM   55  H   UNK     0       5.738  -2.560   0.716  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.459   2.211  -1.784  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.239   0.406  -3.115  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.338  -0.569  -1.886  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.463   0.482  -3.007  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.898   2.140  -2.429  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.386   1.775   2.982  0.00  0.00           H+0
HETATM   62  H   UNK     0      -1.896   3.079   1.867  0.00  0.00           H+0
HETATM   63  H   UNK     0      -1.001   2.602   0.409  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.173   3.655   1.567  0.00  0.00           H+0
HETATM   65  H   UNK     0      -1.124   0.203   3.393  0.00  0.00           H+0
HETATM   66  H   UNK     0      -3.024  -1.823  -2.813  0.00  0.00           H+0
HETATM   67  H   UNK     0      -4.795  -2.010  -3.241  0.00  0.00           H+0
HETATM   68  H   UNK     0      -2.697  -3.866  -3.367  0.00  0.00           H+0
HETATM   69  H   UNK     0      -3.727  -4.988  -1.648  0.00  0.00           H+0
HETATM   70  H   UNK     0      -3.657  -4.493   0.128  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2    1    3    4   38                                             
CONECT    3    2   39   40   41                                             
CONECT    4    2    5   42   43                                             
CONECT    5    4    6   28   44                                             
CONECT    6    5    7   45                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   25   46                                             
CONECT   10    9   11   47                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   22   48                                             
CONECT   14   13   15   49                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   50                                             
CONECT   18   17   51   52   53                                             
CONECT   19   17   20   21                                                  
CONECT   20   19   54   55                                                  
CONECT   21   19                                                            
CONECT   22   13   23   24   56                                             
CONECT   23   22   57   58   59                                             
CONECT   24   22   60                                                       
CONECT   25    9   26   27   61                                             
CONECT   26   25   62   63   64                                             
CONECT   27   25   65                                                       
CONECT   28    5   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   33   34                                             
CONECT   31   30   32   66   67                                             
CONECT   32   31   68                                                       
CONECT   33   30   34   69   70                                             
CONECT   34   33   30                                                       
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    2                                                            
CONECT   39    3                                                            
CONECT   40    3                                                            
CONECT   41    3                                                            
CONECT   42    4                                                            
CONECT   43    4                                                            
CONECT   44    5                                                            
CONECT   45    6                                                            
CONECT   46    9                                                            
CONECT   47   10                                                            
CONECT   48   13                                                            
CONECT   49   14                                                            
CONECT   50   17                                                            
CONECT   51   18                                                            
CONECT   52   18                                                            
CONECT   53   18                                                            
CONECT   54   20                                                            
CONECT   55   20                                                            
CONECT   56   22                                                            
CONECT   57   23                                                            
CONECT   58   23                                                            
CONECT   59   23                                                            
CONECT   60   24                                                            
CONECT   61   25                                                            
CONECT   62   26                                                            
CONECT   63   26                                                            
CONECT   64   26                                                            
CONECT   65   27                                                            
CONECT   66   31                                                            
CONECT   67   31                                                            
CONECT   68   32                                                            
CONECT   69   33                                                            
CONECT   70   33                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  140    0
END

RDKit          3D

70 70  0  0  0  0  0  0  0  0999 V2000
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   -5.5459    0.6677   -0.8894 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3639    1.8369   -0.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3009    0.5947   -0.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2805   -0.4529   -0.4631 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.9930    0.3692    0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8168    0.7460   -1.0262 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0913    0.5969    1.1640 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2215    1.2727    0.5469 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4952    0.6925    0.5554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6171   -0.4429    1.1222 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7280    1.2685   -0.0303 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8783    0.4159    0.2193 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9919    0.8042    0.9798 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0106    1.9475    1.4817 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7080   -1.2035    2.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5769    1.5858   -1.4868 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3911    0.3959   -2.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3925    1.5730    2.2446 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.9546   -2.1824    0.9681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2005   -2.7841   -1.2577 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -5.2558   -3.6483   -0.9551 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.6955    1.5160    0.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2291    2.0841   -0.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8200    1.6234   -0.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0562    2.1900    0.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9222    2.2253    0.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0010    2.6016    0.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1243    0.2031    3.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0242   -1.8235   -2.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7945   -2.0104   -3.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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 14 49  1  0
 17 50  1  6
 18 51  1  0
 18 52  1  0
 18 53  1  0
 20 54  1  0
 20 55  1  0
 22 56  1  6
 23 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 25 61  1  1
 26 62  1  0
 26 63  1  0
 26 64  1  0
 27 65  1  0
 31 66  1  0
 31 67  1  0
 32 68  1  0
 33 69  1  0
 33 70  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2S)-N'-[(1S)-2-hydroxy-1-{[(1S)-2-hydroxy-1-({1-[2-(hydroxymethyl)oxiran-2-yl]-4-methyl-1-oxopentan-2-yl}-C-hydroxycarbonimidoyl)propyl]-C-hydroxycarbonimidoyl}propyl]-2-methylpropanediimidate	Generator

Chemical Formula

C₂₁H₃₆N₄O₉

Average Mass

488.5380 Da

Monoisotopic Mass

488.24823 Da

IUPAC Name

(2S)-N'-[(1S,2R)-2-hydroxy-1-{[(1S,2R)-2-hydroxy-1-{[(2R)-1-[(2R)-2-(hydroxymethyl)oxiran-2-yl]-4-methyl-1-oxopentan-2-yl]carbamoyl}propyl]carbamoyl}propyl]-2-methylpropanediamide

Traditional Name

(2S)-N'-[(1S,2R)-2-hydroxy-1-{[(1S,2R)-2-hydroxy-1-{[(2R)-1-[(2R)-2-(hydroxymethyl)oxiran-2-yl]-4-methyl-1-oxopentan-2-yl]carbamoyl}propyl]carbamoyl}propyl]-2-methylpropanediamide

CAS Registry Number

Not Available

SMILES

CC(C)CC(NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](C)C(N)=O)C(C)O)C(C)O)C(=O)C1(CO)CO1

InChI Identifier

InChI=1S/C21H36N4O9/c1-9(2)6-13(16(29)21(7-26)8-34-21)23-19(32)14(11(4)27)25-20(33)15(12(5)28)24-18(31)10(3)17(22)30/h9-15,26-28H,6-8H2,1-5H3,(H2,22,30)(H,23,32)(H,24,31)(H,25,33)/t10-,11?,12?,13?,14-,15-,21?/m0/s1

InChI Key

SCVCWUHUBWSKHS-VQSWLDGRSA-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
Streptomyces sp.	NPAtlas	11099231
Streptomyces sp. TC 1087	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Hybrid peptides

Direct Parent

Hybrid peptides

Alternative Parents

Substituents

Hybrid peptide
Alpha-dipeptide
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Beta-hydroxy ketone
Fatty amide
Fatty acyl
1,3-dicarbonyl compound
N-acyl-amine
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Primary carboxylic acid amide
Ketone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Organic oxide
Primary alcohol
Organooxygen compound
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.2	ALOGPS
logP	-2.6	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	11.47	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	220.68 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	116.91 m³·mol⁻¹	ChemAxon
Polarizability	49.31 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA016366

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8566224

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10390782

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Koguchi Y, Nishio M, Suzuki S, Takahashi K, Ohnuki T, Komatsubara S: TMC-89A and B, new proteasome inhibitors from streptomyces sp. TC 1087. J Antibiot (Tokyo). 2000 Sep;53(9):967-72. doi: 10.7164/antibiotics.53.967. [PubMed:11099231 ]

Showing NP-Card for TMC-89B (NP0003558)

MOL for NP0003558 (TMC-89B)

3D MOL for NP0003558 (TMC-89B)

3D SDF for NP0003558 (TMC-89B)

3D-SDF for NP0003558 (TMC-89B)

PDB for NP0003558 (TMC-89B)

3D PDB for NP0003558 (TMC-89B)

SMILES for NP0003558 (TMC-89B)

INCHI for NP0003558 (TMC-89B)

Structure for NP0003558 (TMC-89B)

3D Structure for NP0003558 (TMC-89B)