MiMeDB: Showing metabocard for Syringostatin B (MMDBc0010708)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 02:47:33 UTC

Update Date

2022-08-31 06:32:07 UTC

Metabolite ID

MMDBc0010708

Metabolite Identification

Common Name

Syringostatin B

Description

2-[21,24-bis(2-aminoethyl)-15-(3-aminopropyl)-3-(2-chloro-1-hydroxyethyl)-9-ethylidene-5,8,11,14,17,20,23,26-octahydroxy-12-(1-hydroxyethyl)-18-(2-hydroxyethyl)-2-oxo-27-[(1,3,4-trihydroxytetradecylidene)amino]-1-oxa-4,7,10,13,16,19,22,25-octaazacyclooctacosa-4,7,10,13,16,19,22,25-octaen-6-yl]-2-hydroxyacetic acid belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. Based on a literature review very few articles have been published on 2-[21,24-bis(2-aminoethyl)-15-(3-aminopropyl)-3-(2-chloro-1-hydroxyethyl)-9-ethylidene-5,8,11,14,17,20,23,26-octahydroxy-12-(1-hydroxyethyl)-18-(2-hydroxyethyl)-2-oxo-27-[(1,3,4-trihydroxytetradecylidene)amino]-1-oxa-4,7,10,13,16,19,22,25-octaazacyclooctacosa-4,7,10,13,16,19,22,25-octaen-6-yl]-2-hydroxyacetic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152104472D          

 83 83  0  0  0  0            999 V2000
  -10.0026   -0.8250    0.0000 C   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    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -0.8250    0.0000 C   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
   -5.7158   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.0625    0.0000 C   0  0  0  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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8592   -0.4125    0.0000 C   0  0  0  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
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    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4302    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2868    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   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
    2.8579   -2.4750    0.0000 O   0  0  0  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
    7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1073    2.5612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2295    1.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20 16  1  0  0  0  0
 21 17  1  0  0  0  0
 22 18  1  0  0  0  0
 26  3  1  0  0  0  0
 27  5  2  0  0  0  0
 28 14  1  0  0  0  0
 29 16  1  0  0  0  0
 30 17  1  0  0  0  0
 31 18  1  0  0  0  0
 32 25  1  0  0  0  0
 33 15  1  0  0  0  0
 34 23  1  0  0  0  0
 34 33  1  0  0  0  0
 35 24  1  0  0  0  0
 36 23  1  0  0  0  0
 37 26  1  0  0  0  0
 38 35  1  0  0  0  0
 40 39  1  0  0  0  0
 41 27  1  0  0  0  0
 42 30  1  0  0  0  0
 43 29  1  0  0  0  0
 44 31  1  0  0  0  0
 45 28  1  0  0  0  0
 46 32  1  0  0  0  0
 47 37  1  0  0  0  0
 48 39  1  0  0  0  0
 49 40  1  0  0  0  0
 50 38  1  0  0  0  0
 51 24  1  0  0  0  0
 52 19  1  0  0  0  0
 53 20  1  0  0  0  0
 54 21  1  0  0  0  0
 55 32  1  4  0  0  0
 55 36  2  0  0  0  0
 56 27  1  4  0  0  0
 56 47  2  0  0  0  0
 57 28  1  4  0  0  0
 57 44  2  0  0  0  0
 58 29  1  4  0  0  0
 58 42  2  0  0  0  0
 59 30  1  4  0  0  0
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 61 37  1  4  0  0  0
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 62 38  1  4  0  0  0
 62 48  2  0  0  0  0
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 81 50  2  0  0  0  0
 82 25  1  0  0  0  0
 82 50  1  0  0  0  0
 83  5  1  0  0  0  0
M  END


  Mrv1652305152104472D          

 83 83  0  0  0  0            999 V2000
  -10.0026   -0.8250    0.0000 C   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    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -0.8250    0.0000 C   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
   -5.7158   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   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
    2.8579   -2.4750    0.0000 O   0  0  0  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
    7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1073    2.5612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2295    1.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20 16  1  0  0  0  0
 21 17  1  0  0  0  0
 22 18  1  0  0  0  0
 26  3  1  0  0  0  0
 27  5  2  0  0  0  0
 28 14  1  0  0  0  0
 29 16  1  0  0  0  0
 30 17  1  0  0  0  0
 31 18  1  0  0  0  0
 32 25  1  0  0  0  0
 33 15  1  0  0  0  0
 34 23  1  0  0  0  0
 34 33  1  0  0  0  0
 35 24  1  0  0  0  0
 36 23  1  0  0  0  0
 37 26  1  0  0  0  0
 38 35  1  0  0  0  0
 40 39  1  0  0  0  0
 41 27  1  0  0  0  0
 42 30  1  0  0  0  0
 43 29  1  0  0  0  0
 44 31  1  0  0  0  0
 45 28  1  0  0  0  0
 46 32  1  0  0  0  0
 47 37  1  0  0  0  0
 48 39  1  0  0  0  0
 49 40  1  0  0  0  0
 50 38  1  0  0  0  0
 51 24  1  0  0  0  0
 52 19  1  0  0  0  0
 53 20  1  0  0  0  0
 54 21  1  0  0  0  0
 55 32  1  4  0  0  0
 55 36  2  0  0  0  0
 56 27  1  4  0  0  0
 56 47  2  0  0  0  0
 57 28  1  4  0  0  0
 57 44  2  0  0  0  0
 58 29  1  4  0  0  0
 58 42  2  0  0  0  0
 59 30  1  4  0  0  0
 59 46  2  0  0  0  0
 60 31  1  4  0  0  0
 60 43  2  0  0  0  0
 61 37  1  4  0  0  0
 61 45  2  0  0  0  0
 62 38  1  4  0  0  0
 62 48  2  0  0  0  0
 63 39  1  4  0  0  0
 63 41  2  0  0  0  0
 64 22  1  0  0  0  0
 65 26  1  0  0  0  0
 66 33  1  0  0  0  0
 67 34  1  0  0  0  0
 68 35  1  0  0  0  0
 69 36  1  0  0  0  0
 70 40  1  0  0  0  0
 71 41  1  0  0  0  0
 72 42  1  0  0  0  0
 73 43  1  0  0  0  0
 74 44  1  0  0  0  0
 75 45  1  0  0  0  0
 76 46  1  0  0  0  0
 77 47  1  0  0  0  0
 78 48  1  0  0  0  0
 79 49  2  0  0  0  0
 80 49  1  0  0  0  0
 81 50  2  0  0  0  0
 82 25  1  0  0  0  0
 82 50  1  0  0  0  0
 83  5  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0010708

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(C)=C1N=C(O)C(N=C(O)C(CCCN)N=C(O)C(CCO)N=C(O)C(CCN)N=C(O)C(CCN)N=C(O)C(COC(=O)C(N=C(O)C(N=C1O)C(O)C(O)=O)C(O)CCl)N=C(O)CC(O)C(O)CCCCCCCCCC)C(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C50H87ClN12O19/c1-4-6-7-8-9-10-11-12-15-33(66)34(67)23-36(69)55-32-25-82-50(81)38(35(68)24-51)62-48(78)39(40(70)49(79)80)63-41(71)27(5-2)56-47(77)37(26(3)65)61-45(75)28(14-13-19-52)57-44(74)31(18-22-64)60-43(73)29(16-20-53)58-42(72)30(17-21-54)59-46(32)76/h5,26,28-35,37-40,64-68,70H,4,6-25,52-54H2,1-3H3,(H,55,69)(H,56,77)(H,57,74)(H,58,72)(H,59,76)(H,60,73)(H,61,75)(H,62,78)(H,63,71)(H,79,80)/b27-5-

> <INCHI_KEY>
FXAAMFXCTWRSIJ-HCEIJDMSSA-N

> <FORMULA>
C50H87ClN12O19

> <MOLECULAR_WEIGHT>
1195.76

> <EXACT_MASS>
1194.5898963

> <JCHEM_ACCEPTOR_COUNT>
30

> <JCHEM_ATOM_COUNT>
169

> <JCHEM_AVERAGE_POLARIZABILITY>
121.97488339217247

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
19

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(9Z)-21,24-bis(2-aminoethyl)-15-(3-aminopropyl)-3-(2-chloro-1-hydroxyethyl)-9-ethylidene-5,8,11,14,17,20,23,26-octahydroxy-12-(1-hydroxyethyl)-18-(2-hydroxyethyl)-2-oxo-27-[(1,3,4-trihydroxytetradecylidene)amino]-1-oxa-4,7,10,13,16,19,22,25-octaazacyclooctacosa-4,7,10,13,16,19,22,25-octaen-6-yl]-2-hydroxyacetic acid

> <ALOGPS_LOGP>
-0.31

> <JCHEM_LOGP>
-0.491528886666667

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
2.6977087002186173

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.2413809885757208

> <JCHEM_POLAR_SURFACE_AREA>
556.3500000000003

> <JCHEM_REFRACTIVITY>
294.4212999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
27

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.60e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(9Z)-21,24-bis(2-aminoethyl)-15-(3-aminopropyl)-3-(2-chloro-1-hydroxyethyl)-9-ethylidene-5,8,11,14,17,20,23,26-octahydroxy-12-(1-hydroxyethyl)-18-(2-hydroxyethyl)-2-oxo-27-[(1,3,4-trihydroxytetradecylidene)amino]-1-oxa-4,7,10,13,16,19,22,25-octaazacyclooctacosa-4,7,10,13,16,19,22,25-octaen-6-yl](hydroxy)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0     -18.672  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -17.338  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -16.004  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -14.670  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -13.337  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -10.669  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.004  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003  -3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.338  -3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.670   3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   51 Cl   UNK     0       4.001   5.390   0.000  0.00  0.00          Cl+0
HETATM   52  N   UNK     0      17.338  -5.390   0.000  0.00  0.00           N+0
HETATM   53  N   UNK     0       6.668  -6.930   0.000  0.00  0.00           N+0
HETATM   54  N   UNK     0       2.667  -6.160   0.000  0.00  0.00           N+0
HETATM   55  N   UNK     0      -0.000  -1.540   0.000  0.00  0.00           N+0
HETATM   56  N   UNK     0      12.003   2.310   0.000  0.00  0.00           N+0
HETATM   57  N   UNK     0      14.670  -2.310   0.000  0.00  0.00           N+0
HETATM   58  N   UNK     0       6.668  -2.310   0.000  0.00  0.00           N+0
HETATM   59  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   60  N   UNK     0      10.669  -3.080   0.000  0.00  0.00           N+0
HETATM   61  N   UNK     0      16.004   1.540   0.000  0.00  0.00           N+0
HETATM   62  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
HETATM   63  N   UNK     0       8.002   1.540   0.000  0.00  0.00           N+0
HETATM   64  O   UNK     0      10.669  -6.160   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      16.004   4.620   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0      -4.001   0.770   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   69  O   UNK     0      -1.334   0.770   0.000  0.00  0.00           O+0
HETATM   70  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   71  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   72  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   73  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0      13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   75  O   UNK     0      17.338  -0.770   0.000  0.00  0.00           O+0
HETATM   76  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   77  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
HETATM   78  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   79  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   80  O   UNK     0       9.534   4.781   0.000  0.00  0.00           O+0
HETATM   81  O   UNK     0       0.428   3.556   0.000  0.00  0.00           O+0
HETATM   82  O   UNK     0      -0.000   1.540   0.000  0.00  0.00           O+0
HETATM   83  H   UNK     0      10.669  -1.540   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2    5                                                            
CONECT    3   26                                                            
CONECT    4    1    6                                                       
CONECT    5    2   27   83                                                  
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   15                                                       
CONECT   13   14   19                                                       
CONECT   14   13   28                                                       
CONECT   15   12   33                                                       
CONECT   16   20   29                                                       
CONECT   17   21   30                                                       
CONECT   18   22   31                                                       
CONECT   19   13   52                                                       
CONECT   20   16   53                                                       
CONECT   21   17   54                                                       
CONECT   22   18   64                                                       
CONECT   23   34   36                                                       
CONECT   24   35   51                                                       
CONECT   25   32   82                                                       
CONECT   26    3   37   65                                                  
CONECT   27    5   41   56                                                  
CONECT   28   14   45   57                                                  
CONECT   29   16   43   58                                                  
CONECT   30   17   42   59                                                  
CONECT   31   18   44   60                                                  
CONECT   32   25   46   55                                                  
CONECT   33   15   34   66                                                  
CONECT   34   23   33   67                                                  
CONECT   35   24   38   68                                                  
CONECT   36   23   55   69                                                  
CONECT   37   26   47   61                                                  
CONECT   38   35   50   62                                                  
CONECT   39   40   48   63                                                  
CONECT   40   39   49   70                                                  
CONECT   41   27   63   71                                                  
CONECT   42   30   58   72                                                  
CONECT   43   29   60   73                                                  
CONECT   44   31   57   74                                                  
CONECT   45   28   61   75                                                  
CONECT   46   32   59   76                                                  
CONECT   47   37   56   77                                                  
CONECT   48   39   62   78                                                  
CONECT   49   40   79   80                                                  
CONECT   50   38   81   82                                                  
CONECT   51   24                                                            
CONECT   52   19                                                            
CONECT   53   20                                                            
CONECT   54   21                                                            
CONECT   55   32   36                                                       
CONECT   56   27   47                                                       
CONECT   57   28   44                                                       
CONECT   58   29   42                                                       
CONECT   59   30   46                                                       
CONECT   60   31   43                                                       
CONECT   61   37   45                                                       
CONECT   62   38   48                                                       
CONECT   63   39   41                                                       
CONECT   64   22                                                            
CONECT   65   26                                                            
CONECT   66   33                                                            
CONECT   67   34                                                            
CONECT   68   35                                                            
CONECT   69   36                                                            
CONECT   70   40                                                            
CONECT   71   41                                                            
CONECT   72   42                                                            
CONECT   73   43                                                            
CONECT   74   44                                                            
CONECT   75   45                                                            
CONECT   76   46                                                            
CONECT   77   47                                                            
CONECT   78   48                                                            
CONECT   79   49                                                            
CONECT   80   49                                                            
CONECT   81   50                                                            
CONECT   82   25   50                                                       
CONECT   83    5                                                            
MASTER        0    0    0    0    0    0    0    0   83    0  166    0
END

Synonyms

Value	Source
2-[21,24-Bis(2-aminoethyl)-15-(3-aminopropyl)-3-(2-chloro-1-hydroxyethyl)-9-ethylidene-5,8,11,14,17,20,23,26-octahydroxy-12-(1-hydroxyethyl)-18-(2-hydroxyethyl)-2-oxo-27-[(1,3,4-trihydroxytetradecylidene)amino]-1-oxa-4,7,10,13,16,19,22,25-octaazacyclooctacosa-4,7,10,13,16,19,22,25-octaen-6-yl]-2-hydroxyacetate	Generator

Molecular Formula

C₅₀H₈₇ClN₁₂O₁₉

Average Mass

1195.76

Monoisotopic Mass

1194.5898963

IUPAC Name

2-[(9Z)-21,24-bis(2-aminoethyl)-15-(3-aminopropyl)-3-(2-chloro-1-hydroxyethyl)-9-ethylidene-5,8,11,14,17,20,23,26-octahydroxy-12-(1-hydroxyethyl)-18-(2-hydroxyethyl)-2-oxo-27-[(1,3,4-trihydroxytetradecylidene)amino]-1-oxa-4,7,10,13,16,19,22,25-octaazacyclooctacosa-4,7,10,13,16,19,22,25-octaen-6-yl]-2-hydroxyacetic acid

Traditional Name

[(9Z)-21,24-bis(2-aminoethyl)-15-(3-aminopropyl)-3-(2-chloro-1-hydroxyethyl)-9-ethylidene-5,8,11,14,17,20,23,26-octahydroxy-12-(1-hydroxyethyl)-18-(2-hydroxyethyl)-2-oxo-27-[(1,3,4-trihydroxytetradecylidene)amino]-1-oxa-4,7,10,13,16,19,22,25-octaazacyclooctacosa-4,7,10,13,16,19,22,25-octaen-6-yl](hydroxy)acetic acid

CAS Registry Number

Not Available

SMILES

[H]C(C)=C1N=C(O)C(N=C(O)C(CCCN)N=C(O)C(CCO)N=C(O)C(CCN)N=C(O)C(CCN)N=C(O)C(COC(=O)C(N=C(O)C(N=C1O)C(O)C(O)=O)C(O)CCl)N=C(O)CC(O)C(O)CCCCCCCCCC)C(C)O

InChI Identifier

InChI=1S/C50H87ClN12O19/c1-4-6-7-8-9-10-11-12-15-33(66)34(67)23-36(69)55-32-25-82-50(81)38(35(68)24-51)62-48(78)39(40(70)49(79)80)63-41(71)27(5-2)56-47(77)37(26(3)65)61-45(75)28(14-13-19-52)57-44(74)31(18-22-64)60-43(73)29(16-20-53)58-42(72)30(17-21-54)59-46(32)76/h5,26,28-35,37-40,64-68,70H,4,6-25,52-54H2,1-3H3,(H,55,69)(H,56,77)(H,57,74)(H,58,72)(H,59,76)(H,60,73)(H,61,75)(H,62,78)(H,63,71)(H,79,80)/b27-5-

InChI Key

FXAAMFXCTWRSIJ-HCEIJDMSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic depsipeptides

Alternative Parents

Substituents

Cyclic depsipeptide
Macrolide lactam
Alpha-amino acid ester
Macrolactam
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Alpha-hydroxy acid
Dicarboxylic acid or derivatives
Fatty amide
Hydroxy acid
Fatty acyl
N-acyl-amine
Amino acid or derivatives
Carboxamide group
Carboxylic acid ester
Chlorohydrin
Amino acid
Halohydrin
Lactam
Lactone
Secondary carboxylic acid amide
Secondary alcohol
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Carboxylic acid
Primary amine
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Alkyl halide
Organic oxygen compound
Alkyl chloride
Organopnictogen compound
Amine
Primary aliphatic amine
Alcohol
Carbonyl group
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.076 g/L	ALOGPS
logP	-0.31	ALOGPS
logP	-0.49	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	2.24	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	30	ChemAxon
Hydrogen Donor Count	19	ChemAxon
Polar Surface Area	556.35 Å²	ChemAxon
Rotatable Bond Count	27	ChemAxon
Refractivity	294.42 m³·mol⁻¹	ChemAxon
Polarizability	121.97 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

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1		Metabolic reconstruction

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78444159

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14467376

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Syringostatin B (MMDBc0010708)

MOL for #<Metabolite:0x00007fdb2d41ed48>

3D MOL for #<Metabolite:0x00007fdb2d41ed48>

3D SDF for #<Metabolite:0x00007fdb2d41ed48>

3D-SDF for #<Metabolite:0x00007fdb2d41ed48>

PDB for #<Metabolite:0x00007fdb2d41ed48>

3D PDB for #<Metabolite:0x00007fdb2d41ed48>

SMILES for #<Metabolite:0x00007fdb2d41ed48>

INCHI for #<Metabolite:0x00007fdb2d41ed48>

Structure for #<Metabolite:0x00007fdb2d41ed48>

3D Structure for #<Metabolite:0x00007fdb2d41ed48>