NP-MRD: Showing NP-Card for n-[12-benzyl-3,6-bis(3,5-dihydroxyphenyl)-5,8,11,14-tetrahydroxy-9-(hydroxymethyl)-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl]-2-[(5-chloro-1h-pyrrol-2-yl)formamido]-3-phenylpropanimidic acid (NP0226480)

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Record Information

Version

2.0

Created at

2022-09-06 05:31:53 UTC

Updated at

2022-09-06 05:31:53 UTC

NP-MRD ID

NP0226480

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[12-benzyl-3,6-bis(3,5-dihydroxyphenyl)-5,8,11,14-tetrahydroxy-9-(hydroxymethyl)-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl]-2-[(5-chloro-1h-pyrrol-2-yl)formamido]-3-phenylpropanimidic acid

Description

Cochinmicin IV 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. Cochinmicin IV is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171513052D          

 67 72  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6585    1.9049    0.0000 O   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
    3.5724    1.2375    0.0000 N   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
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    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
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   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
    2.8579   -2.4750    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
    4.2868   -2.4750    0.0000 C   0  0  0  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
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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
   -0.0000   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -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
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    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
   -0.7145   -3.7125    0.0000 N   0  0  0  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
   -2.1434   -3.7125    0.0000 O   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
   -0.7615   -5.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164   -6.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -6.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3264   -6.8870    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0964   -5.4349    0.0000 N   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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8079    3.6412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    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
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7645    4.0537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 37 42  1  0  0  0  0
 35 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
 46 51  1  0  0  0  0
 10 52  1  0  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  2  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 57 59  2  0  0  0  0
 52 59  1  0  0  0  0
  6 60  1  0  0  0  0
 60 61  2  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 62 64  2  0  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
 65 67  2  0  0  0  0
 60 67  1  0  0  0  0
M  END


  Mrv1533004171513052D          

 67 72  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6585    1.9049    0.0000 O   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
    3.5724    1.2375    0.0000 N   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
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    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
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2868   -2.4750    0.0000 C   0  0  0  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
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5724   -3.7125    0.0000 C   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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
   -0.0000   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1434   -0.4125    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
   -0.7145   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8414   -6.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3264   -6.8870    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.0964   -5.4349    0.0000 N   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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8079    3.6412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    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
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7645    4.0537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
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 12 13  2  0  0  0  0
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 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
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 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  0  0  0  0
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 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
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 36 37  1  0  0  0  0
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 37 42  1  0  0  0  0
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 47 48  1  0  0  0  0
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 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
 46 51  1  0  0  0  0
 10 52  1  0  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  2  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 57 59  2  0  0  0  0
 52 59  1  0  0  0  0
  6 60  1  0  0  0  0
 60 61  2  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 62 64  2  0  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
 65 67  2  0  0  0  0
 60 67  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226480

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(=O)C(NC(=O)C(NC(=O)C(CO)NC(=O)C(CC2=CC=CC=C2)NC(=O)C1NC(=O)C(CC1=CC=CC=C1)NC(=O)C1=CC=C(Cl)N1)C1=CC(O)=CC(O)=C1)C1=CC(O)=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C46H46ClN7O13/c1-23-37(52-42(62)34(15-25-10-6-3-7-11-25)49-40(60)32-12-13-36(47)48-32)44(64)50-33(14-24-8-4-2-5-9-24)41(61)51-35(22-55)43(63)53-38(26-16-28(56)20-29(57)17-26)45(65)54-39(46(66)67-23)27-18-30(58)21-31(59)19-27/h2-13,16-21,23,33-35,37-39,48,55-59H,14-15,22H2,1H3,(H,49,60)(H,50,64)(H,51,61)(H,52,62)(H,53,63)(H,54,65)

> <INCHI_KEY>
IGUQVVLOCYHROT-UHFFFAOYSA-N

> <FORMULA>
C46H46ClN7O13

> <MOLECULAR_WEIGHT>
940.36

> <EXACT_MASS>
939.2842123

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
113

> <JCHEM_AVERAGE_POLARIZABILITY>
91.84560168321323

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[12-benzyl-3,6-bis(3,5-dihydroxyphenyl)-9-(hydroxymethyl)-16-methyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetraazacyclohexadecan-15-yl]-2-[(5-chloro-1H-pyrrol-2-yl)formamido]-3-phenylpropanamide

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
1.5516032983333337

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.293089522283804

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.753824302201318

> <JCHEM_PKA_STRONGEST_BASIC>
-5.6763767747303655

> <JCHEM_POLAR_SURFACE_AREA>
317.84000000000003

> <JCHEM_REFRACTIVITY>
237.44439999999992

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[12-benzyl-3,6-bis(3,5-dihydroxyphenyl)-9-(hydroxymethyl)-16-methyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetraazacyclohexadecan-15-yl]-2-[(5-chloro-1H-pyrrol-2-yl)formamido]-3-phenylpropanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.000   0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.096   3.556   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       6.668   2.310   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       6.668  -0.770   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       4.001  -2.310   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0      -0.000  -3.080   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   43  N   UNK     0      -1.334  -6.930   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -1.421 -10.145   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -1.897 -11.610   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -3.437 -11.610   0.000  0.00  0.00           C+0
HETATM   50 Cl   UNK     0      -4.343 -12.856   0.000  0.00  0.00          Cl+0
HETATM   51  N   UNK     0      -3.913 -10.145   0.000  0.00  0.00           N+0
HETATM   52  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       3.375   6.797   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      -0.000   6.160   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0       3.294   7.567   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   60                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   52                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   20   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    2   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   43                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   37                                                       
CONECT   43   35   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47   51                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   46                                                       
CONECT   52   10   53   59                                                  
CONECT   53   52   54                                                       
CONECT   54   53   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57                                                       
CONECT   57   56   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   52                                                       
CONECT   60    6   61   67                                                  
CONECT   61   60   62                                                       
CONECT   62   61   63   64                                                  
CONECT   63   62                                                            
CONECT   64   62   65                                                       
CONECT   65   64   66   67                                                  
CONECT   66   65                                                            
CONECT   67   65   60                                                       
MASTER        0    0    0    0    0    0    0    0   67    0  144    0
END

View in JSmol

Synonyms

Value	Source
N-[12-Benzyl-3,6-bis(3,5-dihydroxyphenyl)-5,8,11,14-tetrahydroxy-9-(hydroxymethyl)-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl]-2-[(5-chloro-1H-pyrrol-2-yl)formamido]-3-phenylpropanimidate	Generator

Chemical Formula

C₄₆H₄₆ClN₇O₁₃

Average Mass

940.3600 Da

Monoisotopic Mass

939.28421 Da

IUPAC Name

N-[12-benzyl-3,6-bis(3,5-dihydroxyphenyl)-9-(hydroxymethyl)-16-methyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetraazacyclohexadecan-15-yl]-2-[(5-chloro-1H-pyrrol-2-yl)formamido]-3-phenylpropanamide

Traditional Name

N-[12-benzyl-3,6-bis(3,5-dihydroxyphenyl)-9-(hydroxymethyl)-16-methyl-2,5,8,11,14-pentaoxo-1-oxa-4,7,10,13-tetraazacyclohexadecan-15-yl]-2-[(5-chloro-1H-pyrrol-2-yl)formamido]-3-phenylpropanamide

CAS Registry Number

Not Available

SMILES

CC1OC(=O)C(NC(=O)C(NC(=O)C(CO)NC(=O)C(CC2=CC=CC=C2)NC(=O)C1NC(=O)C(CC1=CC=CC=C1)NC(=O)C1=CC=C(Cl)N1)C1=CC(O)=CC(O)=C1)C1=CC(O)=CC(O)=C1

InChI Identifier

InChI=1S/C46H46ClN7O13/c1-23-37(52-42(62)34(15-25-10-6-3-7-11-25)49-40(60)32-12-13-36(47)48-32)44(64)50-33(14-24-8-4-2-5-9-24)41(61)51-35(22-55)43(63)53-38(26-16-28(56)20-29(57)17-26)45(65)54-39(46(66)67-23)27-18-30(58)21-31(59)19-27/h2-13,16-21,23,33-35,37-39,48,55-59H,14-15,22H2,1H3,(H,49,60)(H,50,64)(H,51,61)(H,52,62)(H,53,63)(H,54,65)

InChI Key

IGUQVVLOCYHROT-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Phenylalanine or derivatives
Macrolide lactam
N-acyl-alpha amino acid or derivatives
Macrolactam
Alpha-amino acid ester
Alpha-amino acid amide
Alpha-amino acid or derivatives
Amphetamine or derivatives
N-substituted-alpha-amino acid
Pyrrole-2-carboxylic acid or derivatives
Resorcinol
2-heteroaryl carboxamide
Pyrrole-2-carboxamide
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Aryl chloride
Aryl halide
Fatty amide
Fatty acyl
Monocyclic benzene moiety
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Carboxylic acid ester
Lactam
Carboxamide group
Lactone
Secondary carboxylic acid amide
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organopnictogen compound
Primary alcohol
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	2.78	ALOGPS
logP	1.55	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	8.75	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	317.84 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	237.44 m³·mol⁻¹	ChemAxon
Polarizability	91.85 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

197547

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-[12-benzyl-3,6-bis(3,5-dihydroxyphenyl)-5,8,11,14-tetrahydroxy-9-(hydroxymethyl)-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl]-2-[(5-chloro-1h-pyrrol-2-yl)formamido]-3-phenylpropanimidic acid (NP0226480)

MOL for NP0226480 (n-[12-benzyl-3,6-bis(3,5-dihydroxyphenyl)-5,8,11,14-tetrahydroxy-9-(hydroxymethyl)-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl]-2-[(5-chloro-1h-pyrrol-2-yl)formamido]-3-phenylpropanimidic acid)

3D MOL for NP0226480 (n-[12-benzyl-3,6-bis(3,5-dihydroxyphenyl)-5,8,11,14-tetrahydroxy-9-(hydroxymethyl)-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl]-2-[(5-chloro-1h-pyrrol-2-yl)formamido]-3-phenylpropanimidic acid)

3D SDF for NP0226480 (n-[12-benzyl-3,6-bis(3,5-dihydroxyphenyl)-5,8,11,14-tetrahydroxy-9-(hydroxymethyl)-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl]-2-[(5-chloro-1h-pyrrol-2-yl)formamido]-3-phenylpropanimidic acid)

3D-SDF for NP0226480 (n-[12-benzyl-3,6-bis(3,5-dihydroxyphenyl)-5,8,11,14-tetrahydroxy-9-(hydroxymethyl)-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl]-2-[(5-chloro-1h-pyrrol-2-yl)formamido]-3-phenylpropanimidic acid)

PDB for NP0226480 (n-[12-benzyl-3,6-bis(3,5-dihydroxyphenyl)-5,8,11,14-tetrahydroxy-9-(hydroxymethyl)-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl]-2-[(5-chloro-1h-pyrrol-2-yl)formamido]-3-phenylpropanimidic acid)

3D PDB for NP0226480 (n-[12-benzyl-3,6-bis(3,5-dihydroxyphenyl)-5,8,11,14-tetrahydroxy-9-(hydroxymethyl)-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl]-2-[(5-chloro-1h-pyrrol-2-yl)formamido]-3-phenylpropanimidic acid)

SMILES for NP0226480 (n-[12-benzyl-3,6-bis(3,5-dihydroxyphenyl)-5,8,11,14-tetrahydroxy-9-(hydroxymethyl)-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl]-2-[(5-chloro-1h-pyrrol-2-yl)formamido]-3-phenylpropanimidic acid)

INCHI for NP0226480 (n-[12-benzyl-3,6-bis(3,5-dihydroxyphenyl)-5,8,11,14-tetrahydroxy-9-(hydroxymethyl)-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl]-2-[(5-chloro-1h-pyrrol-2-yl)formamido]-3-phenylpropanimidic acid)

Structure for NP0226480 (n-[12-benzyl-3,6-bis(3,5-dihydroxyphenyl)-5,8,11,14-tetrahydroxy-9-(hydroxymethyl)-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl]-2-[(5-chloro-1h-pyrrol-2-yl)formamido]-3-phenylpropanimidic acid)

3D Structure for NP0226480 (n-[12-benzyl-3,6-bis(3,5-dihydroxyphenyl)-5,8,11,14-tetrahydroxy-9-(hydroxymethyl)-16-methyl-2-oxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10,13-tetraen-15-yl]-2-[(5-chloro-1h-pyrrol-2-yl)formamido]-3-phenylpropanimidic acid)