NP-MRD: Showing NP-Card for (2s)-2-[(3-{[(2s)-2-{[(2s,3s)-1,3-dihydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene)amino]butanoic acid (NP0237643)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 20:51:00 UTC

Updated at

2022-09-06 20:51:00 UTC

NP-MRD ID

NP0237643

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-[(3-{[(2s)-2-{[(2s,3s)-1,3-dihydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene)amino]butanoic acid

Description

Asterinin A belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. (2s)-2-[(3-{[(2s)-2-{[(2s,3s)-1,3-dihydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene)amino]butanoic acid is found in Aster tataricus. Based on a literature review very few articles have been published on Asterinin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062222512D          

 38 39  0  0  1  0            999 V2000
    5.0013   -1.2375    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
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    2.1434   -0.4125    0.0000 O   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
    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  2  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
   -2.1434   -2.8875    0.0000 O   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  1  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6116   -6.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1636   -6.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7511   -7.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9441   -7.4205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   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 C   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 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
    1.4289   -0.0000    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
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  4  5  2  0  0  0  0
  5  6  1  4  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  1  0  0  0
 15 16  2  0  0  0  0
 16 17  1  4  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 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
 22 26  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  6  0  0  0
  8 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
  3 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
M  END

     RDKit          3D

 71 72  0  0  0  0  0  0  0  0999 V2000
    7.0786    0.4297    1.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5219    1.0586    0.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5657    0.6841   -1.0087 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3236    1.1115   -0.7259 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    1.4837   -0.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9959    2.6903    0.2126 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9865    0.7463   -0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1164    0.4162    0.3156 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9622   -0.2940   -0.1882 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2227    0.1676   -0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954    1.4041    0.3410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3280   -0.6643   -0.7257 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7852   -2.0191   -1.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7377   -2.8714   -1.6510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9386    0.0678   -1.7946 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1687    0.1594   -2.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5207    0.9439   -3.1568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2989   -0.4570   -1.3135 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0977    0.5755   -0.6530 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3753    0.5357    0.7404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9093   -0.4224    1.4084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1696    1.5534    1.4039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7514    2.6729    0.8291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4251    3.3854    1.8017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2413    2.6784    2.9749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4902    1.5965    2.6974 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1509   -1.1547   -2.3690 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3377   -1.8456   -1.7371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3792   -2.1178   -2.9811 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7846   -0.4314    1.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9686   -1.7857    1.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5892   -2.5471    2.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0654   -2.0247    3.2623 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8776   -0.6661    3.4478 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2531    0.1210    2.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5928   -0.8203   -1.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6576   -1.3791   -1.4414 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4380   -1.5436   -0.9422 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9372    0.4923    2.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1711    0.9315    1.8289 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8207   -0.6397    1.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4638    2.1587    0.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5504    0.7190   -0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0545    1.0735   -1.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7238    3.4791   -0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3990    1.4787   -1.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1894   -0.1018   -1.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8144    1.3723    0.8061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5163    1.5722    1.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0317   -0.8551    0.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0044   -1.8965   -1.9527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2881   -2.4530   -0.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2485   -3.3681   -0.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6872    1.9301   -3.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8998   -1.2028   -0.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4838    1.3721   -1.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6641    2.9076   -0.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9808    4.3001    1.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6548    2.9910    3.9231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2180    0.9021    3.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4914   -0.3775   -3.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1433   -1.9795   -2.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7576   -1.1664   -0.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1090   -2.8578   -1.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6456   -2.3205   -3.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5828   -2.1816    0.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7172   -3.6092    1.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5616   -2.6495    4.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2410   -0.2120    4.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1102    1.2019    2.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2979   -2.4493   -1.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  3
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 18 27  1  0
 27 28  1  0
 27 29  1  0
  8 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
  3 36  1  0
 36 38  1  0
 36 37  2  0
 26 22  1  0
 35 30  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  2 42  1  0
  2 43  1  0
  3 44  1  6
  6 45  1  0
  7 46  1  0
  7 47  1  0
  8 48  1  1
 11 49  1  0
 12 50  1  1
 13 51  1  0
 13 52  1  0
 14 53  1  0
 17 54  1  0
 18 55  1  1
 19 56  1  0
 23 57  1  0
 24 58  1  0
 25 59  1  0
 26 60  1  0
 27 61  1  6
 28 62  1  0
 28 63  1  0
 28 64  1  0
 29 65  1  0
 31 66  1  0
 32 67  1  0
 33 68  1  0
 34 69  1  0
 35 70  1  0
 38 71  1  0
M  END


  Mrv1652309062222512D          

 38 39  0  0  1  0            999 V2000
    5.0013   -1.2375    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
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    2.1434   -0.4125    0.0000 O   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
    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  2  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
   -2.1434   -2.8875    0.0000 O   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  1  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6116   -6.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1636   -6.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7511   -7.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9441   -7.4205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   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 C   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 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
    1.4289   -0.0000    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
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  4  5  2  0  0  0  0
  5  6  1  4  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  1  0  0  0
 15 16  2  0  0  0  0
 16 17  1  4  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 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
 22 26  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  6  0  0  0
  8 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
  3 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0237643

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](N=C(O)CC(N=C(O)[C@H](CO)N=C(O)[C@@H](NC(=O)C1=CC=CN1)[C@H](C)O)C1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H33N5O8/c1-3-16(25(37)38)27-20(33)12-18(15-8-5-4-6-9-15)28-23(35)19(13-31)29-24(36)21(14(2)32)30-22(34)17-10-7-11-26-17/h4-11,14,16,18-19,21,26,31-32H,3,12-13H2,1-2H3,(H,27,33)(H,28,35)(H,29,36)(H,30,34)(H,37,38)/t14-,16-,18?,19-,21-/m0/s1

> <INCHI_KEY>
WZVDGPHPBNNQBR-ZKGOZZDXSA-N

> <FORMULA>
C25H33N5O8

> <MOLECULAR_WEIGHT>
531.566

> <EXACT_MASS>
531.232913043

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
53.65781504880049

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(3-{[(2S)-2-{[(2S,3S)-1,3-dihydroxy-2-[(1H-pyrrol-2-yl)formamido]butylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene)amino]butanoic acid

> <JCHEM_LOGP>
0.5571141674388854

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.894725939400292

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8008846485734225

> <JCHEM_PKA_STRONGEST_BASIC>
3.413632934267737

> <JCHEM_POLAR_SURFACE_AREA>
220.41999999999996

> <JCHEM_REFRACTIVITY>
135.22370000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(3-{[(2S)-2-{[(2S,3S)-1,3-dihydroxy-2-(1H-pyrrol-2-ylformamido)butylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene)amino]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.000  -3.080   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0      -1.334  -6.930   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      -4.001 -10.010   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.742 -11.694   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -7.772 -12.838   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -7.002 -14.172   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      -5.496 -13.852   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   30                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   22                                                       
CONECT   27   18   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    8   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
CONECT   36    3   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₃N₅O₈

Average Mass

531.5660 Da

Monoisotopic Mass

531.23291 Da

IUPAC Name

(2S)-2-[(3-{[(2S)-2-{[(2S,3S)-1,3-dihydroxy-2-[(1H-pyrrol-2-yl)formamido]butylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene)amino]butanoic acid

Traditional Name

(2S)-2-[(3-{[(2S)-2-{[(2S,3S)-1,3-dihydroxy-2-(1H-pyrrol-2-ylformamido)butylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene)amino]butanoic acid

CAS Registry Number

Not Available

SMILES

CC[C@H](N=C(O)CC(N=C(O)[C@H](CO)N=C(O)[C@@H](NC(=O)C1=CC=CN1)[C@H](C)O)C1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C25H33N5O8/c1-3-16(25(37)38)27-20(33)12-18(15-8-5-4-6-9-15)28-23(35)19(13-31)29-24(36)21(14(2)32)30-22(34)17-10-7-11-26-17/h4-11,14,16,18-19,21,26,31-32H,3,12-13H2,1-2H3,(H,27,33)(H,28,35)(H,29,36)(H,30,34)(H,37,38)/t14-,16-,18?,19-,21-/m0/s1

InChI Key

WZVDGPHPBNNQBR-ZKGOZZDXSA-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

Species Name	Source	Reference
Aster tataricus	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Hybrid peptides

Direct Parent

Hybrid peptides

Alternative Parents

Substituents

Hybrid peptide
Alpha-dipeptide
N-acyl-l-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Serine or derivatives
Alpha-amino acid amide
Beta amino acid or derivatives
Alpha-amino acid or derivatives
N-substituted-alpha-amino acid
2-heteroaryl carboxamide
Pyrrole-2-carboxylic acid or derivatives
Pyrrole-2-carboxamide
Fatty acyl
Benzenoid
Substituted pyrrole
N-acyl-amine
Fatty amide
Monocyclic benzene moiety
Heteroaromatic compound
Pyrrole
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
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	0.56	ChemAxon
pKa (Strongest Acidic)	1.8	ChemAxon
pKa (Strongest Basic)	3.41	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	220.42 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	135.22 m³·mol⁻¹	ChemAxon
Polarizability	53.66 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

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

101667551

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-[(3-{[(2s)-2-{[(2s,3s)-1,3-dihydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene)amino]butanoic acid (NP0237643)

MOL for NP0237643 ((2s)-2-[(3-{[(2s)-2-{[(2s,3s)-1,3-dihydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene)amino]butanoic acid)

3D MOL for NP0237643 ((2s)-2-[(3-{[(2s)-2-{[(2s,3s)-1,3-dihydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene)amino]butanoic acid)

3D SDF for NP0237643 ((2s)-2-[(3-{[(2s)-2-{[(2s,3s)-1,3-dihydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene)amino]butanoic acid)

3D-SDF for NP0237643 ((2s)-2-[(3-{[(2s)-2-{[(2s,3s)-1,3-dihydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene)amino]butanoic acid)

PDB for NP0237643 ((2s)-2-[(3-{[(2s)-2-{[(2s,3s)-1,3-dihydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene)amino]butanoic acid)

3D PDB for NP0237643 ((2s)-2-[(3-{[(2s)-2-{[(2s,3s)-1,3-dihydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene)amino]butanoic acid)

SMILES for NP0237643 ((2s)-2-[(3-{[(2s)-2-{[(2s,3s)-1,3-dihydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene)amino]butanoic acid)

INCHI for NP0237643 ((2s)-2-[(3-{[(2s)-2-{[(2s,3s)-1,3-dihydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene)amino]butanoic acid)

Structure for NP0237643 ((2s)-2-[(3-{[(2s)-2-{[(2s,3s)-1,3-dihydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene)amino]butanoic acid)

3D Structure for NP0237643 ((2s)-2-[(3-{[(2s)-2-{[(2s,3s)-1,3-dihydroxy-2-(1h-pyrrol-2-ylformamido)butylidene]amino}-1,3-dihydroxypropylidene]amino}-1-hydroxy-3-phenylpropylidene)amino]butanoic acid)