NP-MRD: Showing NP-Card for Anabaenopeptilide 202-B (NP0071962)

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Record Information

Version

2.0

Created at

2022-04-28 17:21:17 UTC

Updated at

2022-04-28 17:21:17 UTC

NP-MRD ID

NP0071962

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Anabaenopeptilide 202-B

Description

(2R)-N-[(2S,5S,8R,11R,12S,15R,18S,21S)-8-[(2R)-butan-2-yl]-5-[(3-chloro-4-hydroxyphenyl)methyl]-6,13,16,21-tetrahydroxy-2-[(1S)-1-hydroxyethyl]-15-[2-(4-hydroxyphenyl)ethyl]-4,11-dimethyl-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]Docosa-6,13,16-trien-12-yl]-2-({[(2S)-1-formylpyrrolidin-2-yl](hydroxy)methylidene}amino)pentanediimidic 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. Anabaenopeptilide 202-B is found in Anabaena sp. 202A2/41 and Anabaena sp. 90. Based on a literature review very few articles have been published on (2R)-N-[(2S,5S,8R,11R,12S,15R,18S,21S)-8-[(2R)-butan-2-yl]-5-[(3-chloro-4-hydroxyphenyl)methyl]-6,13,16,21-tetrahydroxy-2-[(1S)-1-hydroxyethyl]-15-[2-(4-hydroxyphenyl)ethyl]-4,11-dimethyl-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]Docosa-6,13,16-trien-12-yl]-2-({[(2S)-1-formylpyrrolidin-2-yl](hydroxy)methylidene}amino)pentanediimidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219212D          

 75 79  0  0  1  0            999 V2000
    9.2411  -10.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5888   -9.8798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862  -11.1695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5382  -11.7826    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3452  -11.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6001  -10.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.9000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0026   -9.0750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -7.8375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.0750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -9.9000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9062  -10.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3705   -9.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1612  -11.1695    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5635  -11.8068    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0118  -12.5907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8557  -11.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7929  -10.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447  -10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158  -10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302  -12.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -11.9625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    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
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 C   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
   10.0026   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7563   -2.8106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3083   -2.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8958   -1.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0888   -1.6545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9278   -3.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7124   -3.8725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2833  -12.5673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 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
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  3 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 25 32  1  0  0  0  0
 24 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 34 39  1  0  0  0  0
 37 40  1  0  0  0  0
 36 41  1  0  0  0  0
 20 42  1  6  0  0  0
 42 43  1  6  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 16 46  1  1  0  0  0
 15 47  1  6  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 53 55  1  0  0  0  0
 50 56  1  1  0  0  0
 56 57  1  0  0  0  0
 57 58  2  0  0  0  0
 59 57  1  6  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 59 63  1  0  0  0  0
 60 64  1  0  0  0  0
 64 65  2  0  0  0  0
 11 66  1  6  0  0  0
 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
 68 69  2  0  0  0  0
 69 70  1  0  0  0  0
 70 71  2  0  0  0  0
 71 72  1  0  0  0  0
 72 73  2  0  0  0  0
 68 73  1  0  0  0  0
 71 74  1  0  0  0  0
  4 75  1  6  0  0  0
M  END

     RDKit          3D

143147  0  0  0  0  0  0  0  0999 V2000
   -2.4257   -1.9510   -5.9256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9471   -1.6396   -4.4959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7198   -2.4804   -3.5499 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5291   -3.9705   -3.7943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6354   -2.1217   -2.0955 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5337   -3.1103   -1.4413 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8802   -2.9001   -1.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6991   -3.7824   -1.5793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4620   -1.7948   -0.3525 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7852   -2.0728    0.3012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7440   -3.1741    1.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1581   -4.4630    1.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1263   -5.4145    2.0209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6757   -5.0827    3.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6123   -5.9833    4.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2588   -3.7983    3.5345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6734   -3.3315    5.1322 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.2870   -2.8424    2.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6025   -0.6056   -1.1976 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4102   -0.7957   -2.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0430    0.6237   -0.9324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7816    1.3807   -1.9468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6905    1.2127    0.3752 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1363    2.6705    0.4861 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5983    2.6931    0.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3891    3.5492   -0.2398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3310    1.0466    0.8155 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1268    1.5305    0.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5581    1.6338   -0.7777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2239    2.0986    1.4203 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0481    2.3846    2.6324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6070    1.0862    3.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1815    0.2260    2.0541 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4482   -0.9216    1.8429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5007    3.2456    0.9874 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3399    3.4001   -0.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2572    4.5205   -0.7536 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3197    2.4724   -0.6739 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5726    3.1585   -1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3803    3.8614   -0.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7730    5.0114    0.6167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8938    6.2621    0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3757    7.3612    0.6262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7253    7.3120    1.8453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2065    8.4361    2.4614 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6034    6.0707    2.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1262    4.9644    1.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5121    1.2876    0.1326 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3604   -0.0531   -0.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7044   -0.8495    0.4333 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9598   -0.5776   -1.5687 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1779   -1.2886   -1.3123 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3748   -0.7014   -0.7854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3670    0.4997   -0.4951 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5851   -1.5002   -0.5908 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6250   -1.1273   -1.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0252    0.3076   -1.5780 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0407    0.7012   -2.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5425    2.0465   -2.5687 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4874   -0.0757   -3.4622 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2211   -1.1715    0.6859 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7330   -2.2136    1.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6546   -3.4289    1.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3639   -1.9106    2.7861 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7932   -2.7940    3.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1631   -1.8428    4.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0092   -0.5384    4.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1041   -0.5498    3.1839 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8344    0.6141    2.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4841    1.7250    3.1737 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9348   -1.3109   -2.3887 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282219212D          

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 44 45  1  0  0  0  0
 16 46  1  1  0  0  0
 15 47  1  6  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 53 55  1  0  0  0  0
 50 56  1  1  0  0  0
 56 57  1  0  0  0  0
 57 58  2  0  0  0  0
 59 57  1  6  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 59 63  1  0  0  0  0
 60 64  1  0  0  0  0
 64 65  2  0  0  0  0
 11 66  1  6  0  0  0
 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
 68 69  2  0  0  0  0
 69 70  1  0  0  0  0
 70 71  2  0  0  0  0
 71 72  1  0  0  0  0
 72 73  2  0  0  0  0
 68 73  1  0  0  0  0
 71 74  1  0  0  0  0
  4 75  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0071962

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](C)[C@H]1NC(=O)[C@H](CC2=CC(Cl)=C(O)C=C2)N(C)C(=O)[C@H]([C@H](C)O)N2[C@@H](O)CC[C@H](NC(=O)[C@@H](CCC3=CC=C(O)C=C3)NC(=O)[C@@H](NC(=O)[C@@H](CCC(N)=O)NC(=O)[C@@H]3CCCN3C=O)[C@@H](C)OC1=O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C50H68ClN9O15/c1-6-25(2)40-50(74)75-27(4)41(57-44(68)33(16-19-38(52)65)53-45(69)35-8-7-21-59(35)24-61)47(71)54-32(15-11-28-9-13-30(63)14-10-28)43(67)55-34-17-20-39(66)60(48(34)72)42(26(3)62)49(73)58(5)36(46(70)56-40)23-29-12-18-37(64)31(51)22-29/h9-10,12-14,18,22,24-27,32-36,39-42,62-64,66H,6-8,11,15-17,19-21,23H2,1-5H3,(H2,52,65)(H,53,69)(H,54,71)(H,55,67)(H,56,70)(H,57,68)/t25-,26+,27-,32-,33-,34+,35+,36+,39+,40-,41+,42+/m1/s1

> <INCHI_KEY>
BHWMXGSIUOZDBI-LEYQWPSFSA-N

> <FORMULA>
C50H68ClN9O15

> <MOLECULAR_WEIGHT>
1070.59

> <EXACT_MASS>
1069.4523402

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
143

> <JCHEM_AVERAGE_POLARIZABILITY>
107.58434533741254

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-N-[(2S,5S,8R,11R,12S,15R,18S,21S)-8-[(2R)-butan-2-yl]-5-[(3-chloro-4-hydroxyphenyl)methyl]-21-hydroxy-2-[(1S)-1-hydroxyethyl]-15-[2-(4-hydroxyphenyl)ethyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosan-12-yl]-2-{[(2S)-1-formylpyrrolidin-2-yl]formamido}pentanediamide

> <ALOGPS_LOGP>
1.43

> <JCHEM_LOGP>
-1.0582073459999999

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.511054545774968

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.927299264714497

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4632745508656733

> <JCHEM_POLAR_SURFACE_AREA>
356.73999999999995

> <JCHEM_REFRACTIVITY>
265.19520000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-N-[(2S,5S,8R,11R,12S,15R,18S,21S)-8-[(2R)-butan-2-yl]-5-[(3-chloro-4-hydroxyphenyl)methyl]-21-hydroxy-2-[(1S)-1-hydroxyethyl]-15-[2-(4-hydroxyphenyl)ethyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosan-12-yl]-2-{[(2S)-1-formylpyrrolidin-2-yl]formamido}pentanediamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      17.250 -19.385   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      16.032 -18.442   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      16.774 -20.850   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      17.805 -21.994   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.311 -21.674   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.787 -20.209   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.672 -18.480   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      18.672 -16.940   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      17.338 -16.170   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      16.004 -16.940   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      17.338 -14.630   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      16.004 -13.860   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      17.338 -11.550   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      12.003 -14.630   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.669 -16.940   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      13.337 -16.940   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      13.337 -18.480   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      14.758 -19.385   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      15.625 -18.112   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      15.234 -20.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.119 -22.039   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      14.955 -23.503   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.797 -21.935   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.680 -19.873   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.003 -17.710   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.003 -19.250   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.337 -20.020   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.337 -21.560   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.003 -22.330   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.669 -21.560   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      10.669 -20.020   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      12.003 -23.870   0.000  0.00  0.00           O+0
HETATM   41 Cl   UNK     0      14.670 -22.330   0.000  0.00  0.00          Cl+0
HETATM   42  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       9.336 -16.170   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   47  N   UNK     0      14.670 -10.010   0.000  0.00  0.00           N+0
HETATM   48  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      17.338 -10.010   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   55  N   UNK     0      13.337  -3.080   0.000  0.00  0.00           N+0
HETATM   56  N   UNK     0      17.338  -6.930   0.000  0.00  0.00           N+0
HETATM   57  C   UNK     0      17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      16.004  -4.620   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      18.672  -4.620   0.000  0.00  0.00           C+0
HETATM   60  N   UNK     0      20.078  -5.246   0.000  0.00  0.00           N+0
HETATM   61  C   UNK     0      21.109  -4.102   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      20.339  -2.768   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      18.832  -3.088   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      20.399  -6.753   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      21.863  -7.229   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      18.672 -13.860   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      20.005 -14.630   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      21.339 -13.860   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      21.339 -12.320   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      22.673 -11.550   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      24.006 -12.320   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      24.006 -13.860   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      22.673 -14.630   0.000  0.00  0.00           C+0
HETATM   74  O   UNK     0      25.340 -11.550   0.000  0.00  0.00           O+0
HETATM   75  O   UNK     0      17.329 -23.459   0.000  0.00  0.00           O+0
CONECT    1    2    3    7                                                  
CONECT    2    1                                                            
CONECT    3    1    4   28                                                  
CONECT    4    3    5   75                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    1    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   66                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   47                                                  
CONECT   16   15   17   46                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   42                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   33                                                  
CONECT   25   24   26   32                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    3   29                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   25                                                            
CONECT   33   24   34                                                       
CONECT   34   33   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   41                                                  
CONECT   37   36   38   40                                                  
CONECT   38   37   39                                                       
CONECT   39   38   34                                                       
CONECT   40   37                                                            
CONECT   41   36                                                            
CONECT   42   20   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44                                                            
CONECT   46   16                                                            
CONECT   47   15   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51   56                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53                                                            
CONECT   56   50   57                                                       
CONECT   57   56   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   60   63                                                  
CONECT   60   59   61   64                                                  
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   59                                                       
CONECT   64   60   65                                                       
CONECT   65   64                                                            
CONECT   66   11   67                                                       
CONECT   67   66   68                                                       
CONECT   68   67   69   73                                                  
CONECT   69   68   70                                                       
CONECT   70   69   71                                                       
CONECT   71   70   72   74                                                  
CONECT   72   71   73                                                       
CONECT   73   72   68                                                       
CONECT   74   71                                                            
CONECT   75    4                                                            
MASTER        0    0    0    0    0    0    0    0   75    0  158    0
END

View in JSmol

Synonyms

Value	Source
(2R)-N-[(2S,5S,8R,11R,12S,15R,18S,21S)-8-[(2R)-Butan-2-yl]-5-[(3-chloro-4-hydroxyphenyl)methyl]-6,13,16,21-tetrahydroxy-2-[(1S)-1-hydroxyethyl]-15-[2-(4-hydroxyphenyl)ethyl]-4,11-dimethyl-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-2-({[(2S)-1-formylpyrrolidin-2-yl](hydroxy)methylidene}amino)pentanediimidate	Generator

Chemical Formula

C₅₀H₆₈ClN₉O₁₅

Average Mass

1070.5900 Da

Monoisotopic Mass

1069.45234 Da

IUPAC Name

(2R)-N-[(2S,5S,8R,11R,12S,15R,18S,21S)-8-[(2R)-butan-2-yl]-5-[(3-chloro-4-hydroxyphenyl)methyl]-21-hydroxy-2-[(1S)-1-hydroxyethyl]-15-[2-(4-hydroxyphenyl)ethyl]-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosan-12-yl]-2-{[(2S)-1-formylpyrrolidin-2-yl]formamido}pentanediamide

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@@H](C)[C@H]1NC(=O)[C@H](CC2=CC(Cl)=C(O)C=C2)N(C)C(=O)[C@H]([C@H](C)O)N2[C@@H](O)CC[C@H](NC(=O)[C@@H](CCC3=CC=C(O)C=C3)NC(=O)[C@@H](NC(=O)[C@@H](CCC(N)=O)NC(=O)[C@@H]3CCCN3C=O)[C@@H](C)OC1=O)C2=O

InChI Identifier

InChI=1S/C50H68ClN9O15/c1-6-25(2)40-50(74)75-27(4)41(57-44(68)33(16-19-38(52)65)53-45(69)35-8-7-21-59(35)24-61)47(71)54-32(15-11-28-9-13-30(63)14-10-28)43(67)55-34-17-20-39(66)60(48(34)72)42(26(3)62)49(73)58(5)36(46(70)56-40)23-29-12-18-37(64)31(51)22-29/h9-10,12-14,18,22,24-27,32-36,39-42,62-64,66H,6-8,11,15-17,19-21,23H2,1-5H3,(H2,52,65)(H,53,69)(H,54,71)(H,55,67)(H,56,70)(H,57,68)/t25-,26+,27-,32-,33-,34+,35+,36+,39+,40-,41+,42+/m1/s1

InChI Key

BHWMXGSIUOZDBI-LEYQWPSFSA-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
Anabaena sp. 202A2/41	Plant	KNApSAcK
Anabaena sp. 90	Plant	KNApSAcK

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
Macrolactam
Alpha-amino acid ester
Alpha-amino acid or derivatives
2-chlorophenol
2-halophenol
1-hydroxy-2-unsubstituted benzenoid
Piperidinone
Phenol
Halobenzene
Delta-lactam
Chlorobenzene
Benzenoid
Piperidine
Monocyclic benzene moiety
Aryl halide
Aryl chloride
Cyclic carboximidic acid
Tertiary carboxylic acid amide
Pyrrolidine
Secondary alcohol
Lactone
Lactam
Carboxylic acid ester
Carboxamide group
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Alkanolamine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	1.43	ALOGPS
logP	-1.1	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	7.93	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	356.74 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	265.2 m³·mol⁻¹	ChemAxon
Polarizability	107.58 Å³	ChemAxon
Number of Rings	5	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

162918225

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Anabaenopeptilide 202-B (NP0071962)

MOL for NP0071962 (Anabaenopeptilide 202-B)

3D MOL for NP0071962 (Anabaenopeptilide 202-B)

3D SDF for NP0071962 (Anabaenopeptilide 202-B)

3D-SDF for NP0071962 (Anabaenopeptilide 202-B)

PDB for NP0071962 (Anabaenopeptilide 202-B)

3D PDB for NP0071962 (Anabaenopeptilide 202-B)

SMILES for NP0071962 (Anabaenopeptilide 202-B)

INCHI for NP0071962 (Anabaenopeptilide 202-B)

Structure for NP0071962 (Anabaenopeptilide 202-B)

3D Structure for NP0071962 (Anabaenopeptilide 202-B)