NP-MRD: Showing NP-Card for microcyclamide GL546A (NP0039194)

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Record Information

Version

1.0

Created at

2021-06-20 21:41:27 UTC

Updated at

2021-06-30 00:12:23 UTC

NP-MRD ID

NP0039194

Secondary Accession Numbers

None

Natural Product Identification

Common Name

microcyclamide GL546A

Provided By

JEOL Database JEOL Logo

Description

2-[(4S,11S,18R)-11-[(2S)-butan-2-yl]-2,9,16-trihydroxy-4,7-dimethyl-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]Tetracosa-1(21),2,5(24),7,9,12(23),14,16,19(22)-nonaen-18-yl]acetic acid belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides. microcyclamide GL546A is found in Microcystis sp. It was first documented in 2010 (Raveh, A., et al.). Based on a literature review very few articles have been published on 2-[(4S,11S,18R)-11-[(2S)-butan-2-yl]-2,9,16-trihydroxy-4,7-dimethyl-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]Tetracosa-1(21),2,5(24),7,9,12(23),14,16,19(22)-nonaen-18-yl]acetic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123413D          

 63 66  0  0  0  0            999 V2000
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   -2.0699   -3.9993    1.8484 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.5966   -2.0566    2.4468 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202123413D          

 63 66  0  0  0  0            999 V2000
   -2.3163   -5.2261    0.9819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0699   -3.9993    1.8484 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.5966   -2.0566    2.4468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9741   -2.5842   -0.0484 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2936   -1.9964   -0.4628 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3818   -2.7208   -0.8706 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1790   -3.3984   -0.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9798    0.9735   -0.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4889    2.3832   -1.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9065    3.8751    2.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
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  7  6  1  0  0  0  0
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  5  3  1  0  0  0  0
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  3  2  1  0  0  0  0
 20 18  1  0  0  0  0
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  2  1  1  0  0  0  0
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  7  8  2  0  0  0  0
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M  END
> <DATABASE_ID>
NP0039194

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])[C@@]1([H])N([H])C(=O)C2=C([H])SC(=N2)[C@@]([H])(N([H])C(=O)C2=C(OC(=N2)[C@@]([H])(N([H])C(=O)C2=C([H])SC1=N2)C([H])([H])[H])C([H])([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H26N6O6S2/c1-5-9(2)16-23-27-14(8-37-23)19(33)25-12(6-15(30)31)22-26-13(7-36-22)18(32)24-10(3)21-29-17(11(4)35-21)20(34)28-16/h7-10,12,16H,5-6H2,1-4H3,(H,24,32)(H,25,33)(H,28,34)(H,30,31)/t9-,10-,12+,16-/m0/s1

> <INCHI_KEY>
SWMDBTHOKJGFQB-XQDRIVNHSA-N

> <FORMULA>
C23H26N6O6S2

> <MOLECULAR_WEIGHT>
546.62

> <EXACT_MASS>
546.135524929

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
55.22106578332658

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(4S,11S,18R)-11-[(2S)-butan-2-yl]-4,7-dimethyl-2,9,16-trioxo-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1^{5,8}.1^{12,15}]tetracosa-1(21),5(24),7,12(23),14,19(22)-hexaen-18-yl]acetic acid

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
1.6290017366666665

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.519987004568044

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2867872589361773

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8282608509099739

> <JCHEM_POLAR_SURFACE_AREA>
176.40999999999997

> <JCHEM_REFRACTIVITY>
132.01769999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(4S,11S,18R)-11-[(2S)-butan-2-yl]-4,7-dimethyl-2,9,16-trioxo-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1^{5,8}.1^{12,15}]tetracosa-1(21),5(24),7,12(23),14,19(22)-hexaen-18-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 63 66  0  0  0  0  0  0  0  0999 V2000
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 29 61  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.316  -5.226   0.982  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.070  -3.999   1.848  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.863  -3.149   1.398  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.597  -2.057   2.447  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.974  -2.584  -0.048  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.294  -1.996  -0.463  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.382  -2.721  -0.871  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.390  -3.943  -0.969  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.531  -1.876  -1.171  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.504  -0.491  -1.072  0.00  0.00           N+0
HETATM   11  C   UNK     0       3.725  -0.119  -1.419  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.549  -1.159  -1.764  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.781  -2.277  -1.589  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.407  -3.581  -1.870  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.271   1.276  -1.571  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.753   1.385  -1.229  0.00  0.00           C+0
HETATM   17  N   UNK     0       3.400   2.198  -0.854  0.00  0.00           N+0
HETATM   18  C   UNK     0       3.511   2.559   0.466  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.489   2.357   1.174  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.295   3.218   0.958  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.161   3.793   2.207  0.00  0.00           C+0
HETATM   22  S   UNK     0       0.565   4.380   2.423  0.00  0.00           S+0
HETATM   23  C   UNK     0       0.153   3.822   0.851  0.00  0.00           C+0
HETATM   24  N   UNK     0       1.141   3.270   0.171  0.00  0.00           N+0
HETATM   25  C   UNK     0      -1.278   3.860   0.351  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.391   4.672  -0.940  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.182   6.132  -0.672  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.223   6.697   0.407  0.00  0.00           O+0
HETATM   29  O   UNK     0      -0.962   6.829  -1.803  0.00  0.00           O+0
HETATM   30  N   UNK     0      -1.634   2.465   0.124  0.00  0.00           N+0
HETATM   31  C   UNK     0      -2.906   2.001  -0.074  0.00  0.00           C+0
HETATM   32  O   UNK     0      -3.898   2.717  -0.132  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.934   0.543  -0.223  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.046  -0.200  -0.564  0.00  0.00           C+0
HETATM   35  S   UNK     0      -3.637  -1.861  -0.671  0.00  0.00           S+0
HETATM   36  C   UNK     0      -2.023  -1.496  -0.197  0.00  0.00           C+0
HETATM   37  N   UNK     0      -1.772  -0.211  -0.026  0.00  0.00           N+0
HETATM   38  H   UNK     0      -2.644  -4.955  -0.025  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.102  -5.846   1.427  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.411  -5.836   0.899  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.889  -4.348   2.874  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.980  -3.392   1.893  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.011  -3.814   1.423  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.391  -2.508   3.424  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.458  -1.391   2.568  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.274  -1.449   2.181  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.179  -3.398  -0.753  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.399  -0.986  -0.413  0.00  0.00           H+0
HETATM   49  H   UNK     0       5.452  -3.464  -2.174  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.876  -4.096  -2.676  0.00  0.00           H+0
HETATM   51  H   UNK     0       4.385  -4.217  -0.980  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.153   1.548  -2.627  0.00  0.00           H+0
HETATM   53  H   UNK     0       6.086   2.428  -1.253  0.00  0.00           H+0
HETATM   54  H   UNK     0       6.358   0.825  -1.951  0.00  0.00           H+0
HETATM   55  H   UNK     0       5.980   0.974  -0.240  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.489   2.383  -1.263  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.906   3.875   2.986  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.960   4.253   1.115  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.651   4.335  -1.676  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.385   4.561  -1.385  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.867   7.759  -1.505  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.897   1.762   0.130  0.00  0.00           H+0
HETATM   63  H   UNK     0      -5.048   0.153  -0.767  0.00  0.00           H+0
CONECT    1    2   38   39   40                                             
CONECT    2    3    1   41   42                                             
CONECT    3    5    2    4   43                                             
CONECT    4    3   44   45   46                                             
CONECT    5   36    3    6   47                                             
CONECT    6    7    5   48                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9   13   10    7                                                  
CONECT   10   11    9                                                       
CONECT   11   15   12   10                                                  
CONECT   12   13   11                                                       
CONECT   13   12    9   14                                                  
CONECT   14   13   49   50   51                                             
CONECT   15   17   11   16   52                                             
CONECT   16   15   53   54   55                                             
CONECT   17   18   15   56                                                  
CONECT   18   20   17   19                                                  
CONECT   19   18                                                            
CONECT   20   24   18   21                                                  
CONECT   21   20   22   57                                                  
CONECT   22   23   21                                                       
CONECT   23   25   22   24                                                  
CONECT   24   23   20                                                       
CONECT   25   30   23   26   58                                             
CONECT   26   25   27   59   60                                             
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   61                                                       
CONECT   30   31   25   62                                                  
CONECT   31   33   30   32                                                  
CONECT   32   31                                                            
CONECT   33   31   37   34                                                  
CONECT   34   35   33   63                                                  
CONECT   35   34   36                                                       
CONECT   36   35    5   37                                                  
CONECT   37   36   33                                                       
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    2                                                            
CONECT   42    2                                                            
CONECT   43    3                                                            
CONECT   44    4                                                            
CONECT   45    4                                                            
CONECT   46    4                                                            
CONECT   47    5                                                            
CONECT   48    6                                                            
CONECT   49   14                                                            
CONECT   50   14                                                            
CONECT   51   14                                                            
CONECT   52   15                                                            
CONECT   53   16                                                            
CONECT   54   16                                                            
CONECT   55   16                                                            
CONECT   56   17                                                            
CONECT   57   21                                                            
CONECT   58   25                                                            
CONECT   59   26                                                            
CONECT   60   26                                                            
CONECT   61   29                                                            
CONECT   62   30                                                            
CONECT   63   34                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  132    0
END

RDKit          3D

63 66  0  0  0  0  0  0  0  0999 V2000
   -2.3163   -5.2261    0.9819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0699   -3.9993    1.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8634   -3.1490    1.3976 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5966   -2.0566    2.4468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9741   -2.5842   -0.0484 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2936   -1.9964   -0.4628 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3818   -2.7208   -0.8706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3900   -3.9427   -0.9687 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5307   -1.8755   -1.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5040   -0.4905   -1.0721 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7248   -0.1189   -1.4193 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5488   -1.1588   -1.7637 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7813   -2.2774   -1.5889 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4075   -3.5814   -1.8697 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2705    1.2758   -1.5707 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7527    1.3852   -1.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4003    2.1983   -0.8543 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5111    2.5593    0.4658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4885    2.3569    1.1742 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2953    3.2178    0.9581 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1612    3.7934    2.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5654    4.3801    2.4227 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1532    3.8222    0.8510 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1409    3.2703    0.1707 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2777    3.8602    0.3512 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3907    4.6722   -0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1820    6.1317   -0.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2231    6.6971    0.4071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9615    6.8293   -1.8028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6343    2.4645    0.1241 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9061    2.0009   -0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8982    2.7167   -0.1316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9338    0.5434   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0458   -0.2001   -0.5640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6368   -1.8614   -0.6706 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0233   -1.4962   -0.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7720   -0.2107   -0.0260 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6445   -4.9548   -0.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1017   -5.8459    1.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4114   -5.8364    0.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8892   -4.3481    2.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9802   -3.3919    1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0114   -3.8141    1.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3907   -2.5082    3.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4577   -1.3915    2.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2738   -1.4486    2.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1790   -3.3984   -0.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3988   -0.9855   -0.4126 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4522   -3.4636   -2.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8762   -4.0958   -2.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3845   -4.2174   -0.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1533    1.5484   -2.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0858    2.4282   -1.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3581    0.8254   -1.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9798    0.9735   -0.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4889    2.3832   -1.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9065    3.8751    2.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9599    4.2532    1.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6506    4.3353   -1.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3854    4.5605   -1.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8667    7.7588   -1.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8968    1.7619    0.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0477    0.1530   -0.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
 34 35  1  0
 33 31  1  0
  7  6  1  0
 31 30  1  0
 35 36  1  0
 31 32  2  0
 30 25  1  0
  5 36  1  0
 25 23  1  0
 36 37  2  0
 23 22  1  0
  5  3  1  0
 23 24  2  0
 24 20  1  0
  3  2  1  0
 20 18  1  0
 12 13  1  0
 18 17  1  0
  2  1  1  0
 18 19  2  0
 37 33  1  0
 17 15  1  0
  3  4  1  0
 15 11  1  0
 11 12  1  0
 11 10  2  0
 13  9  2  0
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  9 10  1  0
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  9  7  1  0
 27 28  2  0
 13 14  1  0
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  5  6  1  0
 34 63  1  0
  6 48  1  0
  5 47  1  6
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  2 41  1  0
  2 42  1  0
  1 38  1  0
  1 39  1  0
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  4 44  1  0
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 30 62  1  0
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 17 56  1  0
 15 52  1  6
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 16 54  1  0
 16 55  1  0
 26 59  1  0
 26 60  1  0
 21 57  1  0
 29 61  1  0
M  END

View in JSmol

Synonyms

Value	Source
2-[(4S,11S,18R)-11-[(2S)-Butan-2-yl]-2,9,16-trihydroxy-4,7-dimethyl-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1,.1,]tetracosa-1(21),2,5(24),7,9,12(23),14,16,19(22)-nonaen-18-yl]acetate	Generator

Chemical Formula

C₂₃H₂₆N₆O₆S₂

Average Mass

546.6200 Da

Monoisotopic Mass

546.13552 Da

IUPAC Name

2-[(4S,11S,18R)-11-[(2S)-butan-2-yl]-4,7-dimethyl-2,9,16-trioxo-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1^{5,8}.1^{12,15}]tetracosa-1(21),5(24),7,12(23),14,19(22)-hexaen-18-yl]acetic acid

Traditional Name

[(4S,11S,18R)-11-[(2S)-butan-2-yl]-4,7-dimethyl-2,9,16-trioxo-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1^{5,8}.1^{12,15}]tetracosa-1(21),5(24),7,12(23),14,19(22)-hexaen-18-yl]acetic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C([H])([H])[C@@]1([H])N([H])C(=O)C2=C([H])SC(=N2)[C@@]([H])(N([H])C(=O)C2=C(OC(=N2)[C@@]([H])(N([H])C(=O)C2=C([H])SC1=N2)C([H])([H])[H])C([H])([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C23H26N6O6S2/c1-5-9(2)16-23-27-14(8-37-23)19(33)25-12(6-15(30)31)22-26-13(7-36-22)18(32)24-10(3)21-29-17(11(4)35-21)20(34)28-16/h7-10,12,16H,5-6H2,1-4H3,(H,24,32)(H,25,33)(H,28,34)(H,30,31)/t9-,10-,12+,16-/m0/s1

InChI Key

SWMDBTHOKJGFQB-XQDRIVNHSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Microcystis sp.	JEOL database	Raveh, A., et al, Tetrahedron 66, 2705 (2010)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolactams

Sub Class

Not Available

Direct Parent

Macrolactams

Alternative Parents

Substituents

Macrolactam
2-heteroaryl carboxamide
Thiazolecarboxylic acid or derivatives
Azole
Oxazole
Heteroaromatic compound
Thiazole
Carboxamide group
Lactam
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
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	2.06	ALOGPS
logP	1.63	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.29	ChemAxon
pKa (Strongest Basic)	-0.83	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	176.41 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	132.02 m³·mol⁻¹	ChemAxon
Polarizability	55.22 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

78437432

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46197156

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Raveh, A., et al. (2010). Raveh, A., et al, Tetrahedron 66, 2705 (2010). Tetrahedron.

Showing NP-Card for microcyclamide GL546A (NP0039194)

MOL for NP0039194 (microcyclamide GL546A)

3D MOL for NP0039194 (microcyclamide GL546A)

3D SDF for NP0039194 (microcyclamide GL546A)

3D-SDF for NP0039194 (microcyclamide GL546A)

PDB for NP0039194 (microcyclamide GL546A)

3D PDB for NP0039194 (microcyclamide GL546A)

SMILES for NP0039194 (microcyclamide GL546A)

INCHI for NP0039194 (microcyclamide GL546A)

Structure for NP0039194 (microcyclamide GL546A)

3D Structure for NP0039194 (microcyclamide GL546A)