NP-MRD: Showing NP-Card for Cyclo(Pro-Leu-Pro-Ile) (NP0004666)

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Record Information

Version

2.0

Created at

2020-12-09 02:05:49 UTC

Updated at

2021-07-15 16:49:48 UTC

NP-MRD ID

NP0004666

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cyclo(Pro-Leu-Pro-Ile)

Provided By

NPAtlas

Description

(3S,6S,12S,15S)-3-[(2S)-butan-2-yl]-5,14-dihydroxy-12-(2-methylpropyl)-1,4,10,13-tetraazatricyclo[13.3.0.0⁶,¹⁰]Octadeca-4,13-diene-2,11-dione belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone. Cyclo(Pro-Leu-Pro-Ile) is found in Nocardiopsis sp. Cyclo(Pro-Leu-Pro-Ile) was first documented in 2003 (PMID: 12828484). Based on a literature review very few articles have been published on (3S,6S,12S,15S)-3-[(2S)-butan-2-yl]-5,14-dihydroxy-12-(2-methylpropyl)-1,4,10,13-tetraazatricyclo[13.3.0.0⁶,¹⁰]Octadeca-4,13-diene-2,11-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118083D          

 66 68  0  0  0  0            999 V2000
    4.5756   -1.4448    0.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3097   -0.0906    0.7090 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9105    0.1723    1.1319 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4296   -0.7951    2.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9048    0.3698    0.0370 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8544   -0.8193   -0.7889 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1063   -1.9976   -0.4504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7049   -3.0985   -0.5949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2873   -1.9776    0.0444 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5778   -3.3114    0.6798 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8839   -4.1938   -0.4844 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.3225   -3.7150    1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0469   -4.5855   -0.9455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5629   -5.0450   -0.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6263   -3.5374   -1.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1178   -3.4116   -2.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4149    0.6191    0.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6385    1.6598    0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2792    0.6068   -1.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3015   -1.6891   -0.9646 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5318    4.8105   -0.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0816    4.3046   -0.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
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  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
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M  END

     RDKit          3D

 66 68  0  0  0  0  0  0  0  0999 V2000
    4.5756   -1.4448    0.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306242118083D          

 66 68  0  0  0  0            999 V2000
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    4.3097   -0.0906    0.7090 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
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 13  9  1  0  0  0  0
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  1 31  1  0  0  0  0
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  1 33  1  0  0  0  0
  2 34  1  0  0  0  0
  2 35  1  0  0  0  0
  3 36  1  1  0  0  0
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 27 66  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004666

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C(=O)[C@@]2([H])N(C(=O)[C@@]([H])(N([H])C(=O)[C@@]3([H])N(C(=O)[C@]1([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])C3([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H36N4O4/c1-5-14(4)18-22(30)26-11-7-8-16(26)19(27)23-15(12-13(2)3)21(29)25-10-6-9-17(25)20(28)24-18/h13-18H,5-12H2,1-4H3,(H,23,27)(H,24,28)/t14-,15-,16-,17-,18-/m0/s1

> <INCHI_KEY>
RZIIIIQWCVBQRA-ATIWLJMLSA-N

> <FORMULA>
C22H36N4O4

> <MOLECULAR_WEIGHT>
420.554

> <EXACT_MASS>
420.273655655

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
45.24398176956656

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,6S,12S,15S)-3-[(2S)-butan-2-yl]-12-(2-methylpropyl)-1,4,10,13-tetraazatricyclo[13.3.0.0^{6,10}]octadecane-2,5,11,14-tetrone

> <ALOGPS_LOGP>
0.85

> <JCHEM_LOGP>
0.9854292086666672

> <ALOGPS_LOGS>
-1.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.64476320299206

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.112258141210551

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7752518828806045

> <JCHEM_POLAR_SURFACE_AREA>
98.82

> <JCHEM_REFRACTIVITY>
111.83799999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.98e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6S,12S,15S)-3-[(2S)-butan-2-yl]-12-(2-methylpropyl)-1,4,10,13-tetraazatricyclo[13.3.0.0^{6,10}]octadecane-2,5,11,14-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       4.576  -1.445   0.132  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.310  -0.091   0.709  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.910   0.172   1.132  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.430  -0.795   2.197  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.905   0.370   0.037  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.854  -0.819  -0.789  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.106  -1.998  -0.450  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.705  -3.099  -0.595  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.287  -1.978   0.044  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.578  -3.311   0.680  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.884  -4.194  -0.484  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.527  -3.285  -1.482  0.00  0.00           C+0
HETATM   13  N   UNK     0      -1.291  -1.923  -1.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -1.927  -0.754  -1.467  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.402  -0.770  -2.666  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.124   0.509  -0.758  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.533   0.611  -0.248  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.975  -0.414   0.727  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.144  -0.442   1.986  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.248  -1.760   0.136  0.00  0.00           C+0
HETATM   21  N   UNK     0      -1.835   1.667  -1.628  0.00  0.00           N+0
HETATM   22  C   UNK     0      -0.639   2.397  -1.624  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.139   2.713  -2.742  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.118   2.847  -0.426  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.167   4.285  -0.049  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.189   4.895   0.252  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.038   4.151  -0.766  0.00  0.00           C+0
HETATM   28  N   UNK     0       1.550   2.805  -0.654  0.00  0.00           N+0
HETATM   29  C   UNK     0       2.260   1.564  -0.743  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.230   1.527  -1.536  0.00  0.00           O+0
HETATM   31  H   UNK     0       4.548  -1.507  -0.963  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.655  -1.680   0.393  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.004  -2.251   0.608  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.678   0.653   0.001  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.958   0.057   1.635  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.948   1.171   1.683  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.150  -0.759   3.021  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.456  -0.442   2.574  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.380  -1.834   1.833  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.905   0.494   0.540  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.400  -0.790  -1.681  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.438  -1.139   0.778  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.447  -3.277   1.376  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.323  -3.715   1.208  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.047  -4.585  -0.946  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.563  -5.045  -0.198  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.626  -3.537  -1.488  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.118  -3.412  -2.510  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.415   0.619   0.091  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.639   1.660   0.173  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.279   0.607  -1.081  0.00  0.00           H+0
HETATM   52  H   UNK     0      -5.005  -0.048   1.079  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.483   0.449   1.945  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.798  -0.279   2.862  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.606  -1.372   2.166  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.301  -1.689  -0.965  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.543  -2.541   0.484  0.00  0.00           H+0
HETATM   58  H   UNK     0      -5.260  -2.155   0.434  0.00  0.00           H+0
HETATM   59  H   UNK     0      -2.617   1.915  -2.275  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.130   2.247   0.473  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.532   4.811  -0.974  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.886   4.401   0.758  0.00  0.00           H+0
HETATM   63  H   UNK     0       1.243   5.965   0.015  0.00  0.00           H+0
HETATM   64  H   UNK     0       1.529   4.689   1.266  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.898   4.580  -1.780  0.00  0.00           H+0
HETATM   66  H   UNK     0       3.082   4.305  -0.461  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    1    3   34   35                                             
CONECT    3    2    4    5   36                                             
CONECT    4    3   37   38   39                                             
CONECT    5    3    6   29   40                                             
CONECT    6    5    7   41                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   13   42                                             
CONECT   10    9   11   43   44                                             
CONECT   11   10   12   45   46                                             
CONECT   12   11   13   47   48                                             
CONECT   13   12   14    9                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   21   49                                             
CONECT   17   16   18   50   51                                             
CONECT   18   17   19   20   52                                             
CONECT   19   18   53   54   55                                             
CONECT   20   18   56   57   58                                             
CONECT   21   16   22   59                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   28   60                                             
CONECT   25   24   26   61   62                                             
CONECT   26   25   27   63   64                                             
CONECT   27   26   28   65   66                                             
CONECT   28   27   29   24                                                  
CONECT   29   28   30    5                                                  
CONECT   30   29                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    2                                                            
CONECT   35    2                                                            
CONECT   36    3                                                            
CONECT   37    4                                                            
CONECT   38    4                                                            
CONECT   39    4                                                            
CONECT   40    5                                                            
CONECT   41    6                                                            
CONECT   42    9                                                            
CONECT   43   10                                                            
CONECT   44   10                                                            
CONECT   45   11                                                            
CONECT   46   11                                                            
CONECT   47   12                                                            
CONECT   48   12                                                            
CONECT   49   16                                                            
CONECT   50   17                                                            
CONECT   51   17                                                            
CONECT   52   18                                                            
CONECT   53   19                                                            
CONECT   54   19                                                            
CONECT   55   19                                                            
CONECT   56   20                                                            
CONECT   57   20                                                            
CONECT   58   20                                                            
CONECT   59   21                                                            
CONECT   60   24                                                            
CONECT   61   25                                                            
CONECT   62   25                                                            
CONECT   63   26                                                            
CONECT   64   26                                                            
CONECT   65   27                                                            
CONECT   66   27                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  136    0
END

RDKit          3D

66 68  0  0  0  0  0  0  0  0999 V2000
    4.5756   -1.4448    0.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3097   -0.0906    0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9105    0.1723    1.1319 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4296   -0.7951    2.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9048    0.3698    0.0370 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8544   -0.8193   -0.7889 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1063   -1.9976   -0.4504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7049   -3.0985   -0.5949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2873   -1.9776    0.0444 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5778   -3.3114    0.6798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8839   -4.1938   -0.4844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5266   -3.2848   -1.4818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2912   -1.9226   -0.9999 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9267   -0.7540   -1.4668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4023   -0.7698   -2.6662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1240    0.5093   -0.7582 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5327    0.6114   -0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9747   -0.4139    0.7265 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1444   -0.4423    1.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2480   -1.7600    0.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8348    1.6669   -1.6280 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6388    2.3970   -1.6243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1394    2.7128   -2.7421 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1178    2.8466   -0.4261 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1665    4.2849   -0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1888    4.8949    0.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0383    4.1508   -0.7662 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5496    2.8045   -0.6540 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2602    1.5641   -0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2299    1.5271   -1.5355 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6546   -1.6798    0.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0036   -2.2512    0.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6782    0.6530    0.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9579    0.0569    1.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9484    1.1711    1.6829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1504   -0.7592    3.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4565   -0.4421    2.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3803   -1.8342    1.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9045    0.4941    0.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4002   -0.7898   -1.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4384   -1.1385    0.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4467   -3.2767    1.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3225   -3.7150    1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0469   -4.5855   -0.9455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5629   -5.0450   -0.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6263   -3.5374   -1.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1178   -3.4116   -2.5098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4149    0.6191    0.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6385    1.6598    0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2792    0.6068   -1.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0049   -0.0480    1.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4831    0.4485    1.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7983   -0.2793    2.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6060   -1.3717    2.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3015   -1.6891   -0.9646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5429   -2.5412    0.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2595   -2.1550    0.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6166    1.9154   -2.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1300    2.2470    0.4732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5318    4.8105   -0.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8860    4.4006    0.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2434    5.9646    0.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5294    4.6887    1.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8981    4.5805   -1.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0816    4.3046   -0.4613 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 29  5  1  0
 13  9  1  0
 28 24  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  1
  4 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  1
  6 41  1  0
  9 42  1  1
 10 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 16 49  1  1
 17 50  1  0
 17 51  1  0
 18 52  1  1
 19 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 20 57  1  0
 20 58  1  0
 21 59  1  0
 24 60  1  1
 25 61  1  0
 25 62  1  0
 26 63  1  0
 26 64  1  0
 27 65  1  0
 27 66  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Cyclo-(L-isoleucyl-L-prolyl-L-leucyl-L-prolyl)	MeSH
MKN-349a	MeSH
MKN349a	MeSH

Chemical Formula

C₂₂H₃₆N₄O₄

Average Mass

420.5540 Da

Monoisotopic Mass

420.27366 Da

IUPAC Name

(3S,6S,12S,15S)-3-[(2S)-butan-2-yl]-12-(2-methylpropyl)-1,4,10,13-tetraazatricyclo[13.3.0.0^{6,10}]octadecane-2,5,11,14-tetrone

Traditional Name

(3S,6S,12S,15S)-3-[(2S)-butan-2-yl]-12-(2-methylpropyl)-1,4,10,13-tetraazatricyclo[13.3.0.0^{6,10}]octadecane-2,5,11,14-tetrone

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@@H]1NC(=O)[C@@H]2CCCN2C(=O)[C@H](CC(C)C)NC(=O)[C@@H]2CCCN2C1=O

InChI Identifier

InChI=1S/C22H36N4O4/c1-5-14(4)18-22(30)26-11-7-8-16(26)19(27)23-15(12-13(2)3)21(29)25-10-6-9-17(25)20(28)24-18/h13-18H,5-12H2,1-4H3,(H,23,27)(H,24,28)/t14-,15-,16-,17-,18-/m0/s1

InChI Key

RZIIIIQWCVBQRA-ATIWLJMLSA-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
Nocardiopsis sp.	NPAtlas	12828484

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Cyclic peptides

Alternative Parents

Substituents

Cyclic alpha peptide
Macrolactam
Alpha-amino acid or derivatives
Pyrrolidine
Tertiary carboxylic acid amide
Secondary carboxylic acid amide
Lactam
Carboxamide group
Organoheterocyclic compound
Azacycle
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.85	ALOGPS
logP	0.99	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	11.11	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	98.82 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	111.84 m³·mol⁻¹	ChemAxon
Polarizability	45.24 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA013716

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9113944

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10938709

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shin J, Seo Y, Lee HS, Rho JR, Mo SJ: A new cyclic peptide from a marine-derived bacterium of the genus Nocardiopsis. J Nat Prod. 2003 Jun;66(6):883-4. doi: 10.1021/np030075r. [PubMed:12828484 ]

Showing NP-Card for Cyclo(Pro-Leu-Pro-Ile) (NP0004666)

MOL for NP0004666 (Cyclo(Pro-Leu-Pro-Ile))

3D MOL for NP0004666 (Cyclo(Pro-Leu-Pro-Ile))

3D SDF for NP0004666 (Cyclo(Pro-Leu-Pro-Ile))

3D-SDF for NP0004666 (Cyclo(Pro-Leu-Pro-Ile))

PDB for NP0004666 (Cyclo(Pro-Leu-Pro-Ile))

3D PDB for NP0004666 (Cyclo(Pro-Leu-Pro-Ile))

SMILES for NP0004666 (Cyclo(Pro-Leu-Pro-Ile))

INCHI for NP0004666 (Cyclo(Pro-Leu-Pro-Ile))

Structure for NP0004666 (Cyclo(Pro-Leu-Pro-Ile))

3D Structure for NP0004666 (Cyclo(Pro-Leu-Pro-Ile))