NP-MRD: Showing NP-Card for 9-methoxyrebeccamycin (NP0014863)

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Record Information

Version

2.0

Created at

2021-01-05 23:54:48 UTC

Updated at

2021-07-15 17:18:23 UTC

NP-MRD ID

NP0014863

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-methoxyrebeccamycin

Provided By

NPAtlas

Description

9-methoxyrebeccamycin is found in Pseudonocardia sp. 9-methoxyrebeccamycin was first documented in 2015 (PMID: 26535611). Based on a literature review very few articles have been published on 5,21-dichloro-3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-14-hydroxy-7-methoxy-3,13,23-triazahexacyclo[14.7.0.0²,¹⁰.0⁴,⁹.0¹¹,¹⁵.0¹⁷,²²]Tricosa-1,4(9),5,7,10,13,15,17(22),18,20-decaen-12-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120073D          

 64 70  0  0  0  0            999 V2000
   -2.6831    6.2172   -1.9313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2379    5.0331   -1.3969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3923    3.9554   -1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0688    4.0164   -1.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2671    2.8930   -1.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4284    2.9812   -1.5764 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8097    1.7471   -0.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1761    1.7052   -0.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9612    2.7868   -0.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4584    0.4448    0.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6290   -0.1600    0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5997   -1.4961    0.9953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3747   -2.1742    1.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0274   -3.4657    1.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7380   -4.5370    1.8686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0427   -5.7221    2.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6975   -5.8654    1.9229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0119   -4.7578    1.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6616   -3.5682    1.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841   -2.3796    0.6501 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2093   -1.5620    0.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2537   -0.2358    0.1202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2531    0.5313   -0.3374 N   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9591    2.0985    0.8883 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3646    2.8712    1.8880 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8934    0.0672   -0.4168 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1249   -1.2164    0.1151 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5048   -1.3656    0.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2949    0.0146   -1.7688 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7803    0.9510   -2.6634 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8133   -0.0448   -1.6701 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5542   -1.4380   -1.9463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9366   -1.8776    1.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3366   -2.9649    1.8370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7758   -0.7536    1.1479 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9961    0.3120    0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4986    1.4418    0.3303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8180    6.5047   -1.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4250    7.0258   -1.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2951    6.1066   -2.9494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5910    4.9137   -1.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0109    2.7949   -0.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7864   -4.5017    2.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6318   -6.5415    2.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1504   -6.7671    2.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.8011   -0.7253    1.3318 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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
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  9 46  1  0  0  0  0
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 21 50  1  0  0  0  0
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 39 64  1  0  0  0  0
M  END

     RDKit          3D

 64 70  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242120073D          

 64 70  0  0  0  0            999 V2000
   -2.6831    6.2172   -1.9313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2379    5.0331   -1.3969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3923    3.9554   -1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0688    4.0164   -1.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2671    2.8930   -1.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4284    2.9812   -1.5764 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8097    1.7471   -0.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9612    2.7868   -0.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4584    0.4448    0.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0014863

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(N2C3=C4N([H])C5=C(Cl)C([H])=C([H])C([H])=C5C4=C4C(=O)N([H])C(=O)C4=C3C3=C([H])C(OC([H])([H])[H])=C([H])C(Cl)=C23)[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H23Cl2N3O8/c1-39-9-6-11-16-18-17(26(37)32-27(18)38)15-10-4-3-5-12(29)19(10)31-20(15)22(16)33(21(11)13(30)7-9)28-24(36)23(35)25(40-2)14(8-34)41-28/h3-7,14,23-25,28,31,34-36H,8H2,1-2H3,(H,32,37,38)/t14-,23-,24-,25-,28-/m1/s1

> <INCHI_KEY>
HUCOVWGJVBBELT-BJIUMZSASA-N

> <FORMULA>
C28H23Cl2N3O8

> <MOLECULAR_WEIGHT>
600.41

> <EXACT_MASS>
599.0862201

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
59.78238496266909

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,21-dichloro-3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-7-methoxy-3,13,23-triazahexacyclo[14.7.0.0^{2,10}.0^{4,9}.0^{11,15}.0^{17,22}]tricosa-1,4,6,8,10,15,17,19,21-nonaene-12,14-dione

> <ALOGPS_LOGP>
3.32

> <JCHEM_LOGP>
2.4319612919999987

> <ALOGPS_LOGS>
-4.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.373355131697352

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.106004167209642

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9807060813246222

> <JCHEM_POLAR_SURFACE_AREA>
155.27

> <JCHEM_REFRACTIVITY>
147.52600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,21-dichloro-3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-7-methoxy-3,13,23-triazahexacyclo[14.7.0.0^{2,10}.0^{4,9}.0^{11,15}.0^{17,22}]tricosa-1,4,6,8,10,15,17,19,21-nonaene-12,14-dione

> <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      -2.683   6.217  -1.931  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.238   5.033  -1.397  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.392   3.955  -1.168  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.069   4.016  -1.441  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.267   2.893  -1.186  0.00  0.00           C+0
HETATM    6 Cl   UNK     0       1.428   2.981  -1.576  0.00  0.00          Cl+0
HETATM    7  C   UNK     0      -0.810   1.747  -0.667  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.176   1.705  -0.394  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.961   2.787  -0.637  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.458   0.445   0.106  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.629  -0.160   0.535  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.600  -1.496   0.995  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.375  -2.174   1.002  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.027  -3.466   1.371  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.738  -4.537   1.869  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.043  -5.722   2.134  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.698  -5.865   1.923  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.012  -4.758   1.418  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       1.714  -4.890   1.130  0.00  0.00          Cl+0
HETATM   20  C   UNK     0      -0.662  -3.568   1.143  0.00  0.00           C+0
HETATM   21  N   UNK     0      -0.184  -2.380   0.650  0.00  0.00           N+0
HETATM   22  C   UNK     0      -1.209  -1.562   0.572  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.254  -0.236   0.120  0.00  0.00           C+0
HETATM   24  N   UNK     0      -0.253   0.531  -0.337  0.00  0.00           N+0
HETATM   25  C   UNK     0       1.123   0.308  -0.474  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.910   1.276   0.237  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.117   0.830   0.624  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.959   2.099   0.888  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.365   2.871   1.888  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.893   0.067  -0.417  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.125  -1.216   0.115  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.505  -1.366   0.244  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.295   0.015  -1.769  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.780   0.951  -2.663  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.813  -0.045  -1.670  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.554  -1.438  -1.946  0.00  0.00           O+0
HETATM   37  C   UNK     0      -4.937  -1.878   1.382  0.00  0.00           C+0
HETATM   38  O   UNK     0      -5.337  -2.965   1.837  0.00  0.00           O+0
HETATM   39  N   UNK     0      -5.776  -0.754   1.148  0.00  0.00           N+0
HETATM   40  C   UNK     0      -4.996   0.312   0.629  0.00  0.00           C+0
HETATM   41  O   UNK     0      -5.499   1.442   0.330  0.00  0.00           O+0
HETATM   42  H   UNK     0      -1.818   6.505  -1.278  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.425   7.026  -1.870  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.295   6.107  -2.949  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.591   4.914  -1.857  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.011   2.795  -0.441  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.786  -4.502   2.057  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.632  -6.542   2.522  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.150  -6.767   2.120  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.835  -2.350   0.434  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.362  -0.513   0.253  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.142   0.339   1.627  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.999   2.737  -0.021  0.00  0.00           H+0
HETATM   54  H   UNK     0       5.011   1.842   1.121  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.411   2.558   1.972  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.927   0.524  -0.558  0.00  0.00           H+0
HETATM   57  H   UNK     0       5.823  -2.327   0.645  0.00  0.00           H+0
HETATM   58  H   UNK     0       6.041  -1.173  -0.730  0.00  0.00           H+0
HETATM   59  H   UNK     0       5.817  -0.503   0.914  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.679  -0.960  -2.219  0.00  0.00           H+0
HETATM   61  H   UNK     0       3.480   0.706  -3.556  0.00  0.00           H+0
HETATM   62  H   UNK     0       1.447   0.282  -2.660  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.236  -1.981  -1.474  0.00  0.00           H+0
HETATM   64  H   UNK     0      -6.801  -0.725   1.332  0.00  0.00           H+0
CONECT    1    2   42   43   44                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5   45                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   24                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    3   46                                                  
CONECT   10    8   11   23                                                  
CONECT   11   10   12   40                                                  
CONECT   12   11   13   37                                                  
CONECT   13   12   14   22                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16   47                                                  
CONECT   16   15   17   48                                                  
CONECT   17   16   18   49                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   14                                                  
CONECT   21   20   22   50                                                  
CONECT   22   21   23   13                                                  
CONECT   23   22   24   10                                                  
CONECT   24   23   25    7                                                  
CONECT   25   24   26   35   51                                             
CONECT   26   25   27                                                       
CONECT   27   26   28   30   52                                             
CONECT   28   27   29   53   54                                             
CONECT   29   28   55                                                       
CONECT   30   27   31   33   56                                             
CONECT   31   30   32                                                       
CONECT   32   31   57   58   59                                             
CONECT   33   30   34   35   60                                             
CONECT   34   33   61                                                       
CONECT   35   33   36   25   62                                             
CONECT   36   35   63                                                       
CONECT   37   12   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   64                                                  
CONECT   40   39   41   11                                                  
CONECT   41   40                                                            
CONECT   42    1                                                            
CONECT   43    1                                                            
CONECT   44    1                                                            
CONECT   45    4                                                            
CONECT   46    9                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
CONECT   49   17                                                            
CONECT   50   21                                                            
CONECT   51   25                                                            
CONECT   52   27                                                            
CONECT   53   28                                                            
CONECT   54   28                                                            
CONECT   55   29                                                            
CONECT   56   30                                                            
CONECT   57   32                                                            
CONECT   58   32                                                            
CONECT   59   32                                                            
CONECT   60   33                                                            
CONECT   61   34                                                            
CONECT   62   35                                                            
CONECT   63   36                                                            
CONECT   64   39                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  140    0
END

RDKit          3D

64 70  0  0  0  0  0  0  0  0999 V2000
   -2.6831    6.2172   -1.9313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2379    5.0331   -1.3969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3923    3.9554   -1.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0688    4.0164   -1.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2671    2.8930   -1.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4284    2.9812   -1.5764 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8097    1.7471   -0.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1761    1.7052   -0.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9612    2.7868   -0.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4584    0.4448    0.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6290   -0.1600    0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5997   -1.4961    0.9953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3747   -2.1742    1.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0274   -3.4657    1.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7380   -4.5370    1.8686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0427   -5.7221    2.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6975   -5.8654    1.9229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0119   -4.7578    1.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7141   -4.8899    1.1304 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.6616   -3.5682    1.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841   -2.3796    0.6501 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2093   -1.5620    0.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2537   -0.2358    0.1202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2531    0.5313   -0.3374 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1225    0.3079   -0.4743 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9095    1.2761    0.2365 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1170    0.8302    0.6244 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9591    2.0985    0.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3646    2.8712    1.8880 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8934    0.0672   -0.4168 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1249   -1.2164    0.1151 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5048   -1.3656    0.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2949    0.0146   -1.7688 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7803    0.9510   -2.6634 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8133   -0.0448   -1.6701 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5542   -1.4380   -1.9463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9366   -1.8776    1.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3366   -2.9649    1.8370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7758   -0.7536    1.1479 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9961    0.3120    0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4986    1.4418    0.3303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8180    6.5047   -1.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4250    7.0258   -1.8703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2951    6.1066   -2.9494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5910    4.9137   -1.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0109    2.7949   -0.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7864   -4.5017    2.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6318   -6.5415    2.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1504   -6.7671    2.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8346   -2.3498    0.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3622   -0.5126    0.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1420    0.3392    1.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9991    2.7373   -0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0105    1.8421    1.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4108    2.5581    1.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9271    0.5236   -0.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8227   -2.3269    0.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0407   -1.1725   -0.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8173   -0.5030    0.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6787   -0.9599   -2.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4803    0.7059   -3.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4474    0.2817   -2.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2365   -1.9807   -1.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8011   -0.7253    1.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 27 30  1  0
 30 31  1  0
 31 32  1  0
 30 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 12 37  1  0
 37 38  2  0
 37 39  1  0
 39 40  1  0
 40 41  2  0
  9  3  1  0
 23 10  1  0
 35 25  1  0
 24  7  1  0
 40 11  1  0
 22 13  1  0
 20 14  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  4 45  1  0
  9 46  1  0
 15 47  1  0
 16 48  1  0
 17 49  1  0
 21 50  1  0
 25 51  1  1
 27 52  1  1
 28 53  1  0
 28 54  1  0
 29 55  1  0
 30 56  1  6
 32 57  1  0
 32 58  1  0
 32 59  1  0
 33 60  1  6
 34 61  1  0
 35 62  1  6
 36 63  1  0
 39 64  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₈H₂₃Cl₂N₃O₈

Average Mass

600.4100 Da

Monoisotopic Mass

599.08622 Da

IUPAC Name

5,21-dichloro-3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-7-methoxy-3,13,23-triazahexacyclo[14.7.0.0^{2,10}.0^{4,9}.0^{11,15}.0^{17,22}]tricosa-1,4,6,8,10,15,17,19,21-nonaene-12,14-dione

Traditional Name

CAS Registry Number

Not Available

SMILES

CO[C@H]1[C@H](O)[C@@H](O)[C@@H](O[C@@H]1CO)N1C2=C3NC4=C(C=CC=C4Cl)C3=C3C(=O)NC(=O)C3=C2C2=CC(OC)=CC(Cl)=C12

InChI Identifier

InChI=1S/C28H23Cl2N3O8/c1-39-9-6-11-16-18-17(26(37)32-27(18)38)15-10-4-3-5-12(29)19(10)31-20(15)22(16)33(21(11)13(30)7-9)28-24(36)23(35)25(40-2)14(8-34)41-28/h3-7,14,23-25,28,31,34-36H,8H2,1-2H3,(H,32,37,38)/t14-,23-,24-,25-,28-/m1/s1

InChI Key

HUCOVWGJVBBELT-BJIUMZSASA-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
Pseudonocardia sp.	NPAtlas	26535611

Chemical Taxonomy

Classification

Not classified

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	3.32	ALOGPS
logP	2.43	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	8.11	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.27 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	147.53 m³·mol⁻¹	ChemAxon
Polarizability	59.78 Å³	ChemAxon
Number of Rings	7	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

NPAtlas ID

NPA001508

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

40257828

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583513

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Van Arnam EB, Ruzzini AC, Sit CS, Currie CR, Clardy J: A Rebeccamycin Analog Provides Plasmid-Encoded Niche Defense. J Am Chem Soc. 2015 Nov 18;137(45):14272-4. doi: 10.1021/jacs.5b09794. Epub 2015 Nov 10. [PubMed:26535611 ]

Showing NP-Card for 9-methoxyrebeccamycin (NP0014863)

MOL for NP0014863 (9-methoxyrebeccamycin)

3D MOL for NP0014863 (9-methoxyrebeccamycin)

3D SDF for NP0014863 (9-methoxyrebeccamycin)

3D-SDF for NP0014863 (9-methoxyrebeccamycin)

PDB for NP0014863 (9-methoxyrebeccamycin)

3D PDB for NP0014863 (9-methoxyrebeccamycin)

SMILES for NP0014863 (9-methoxyrebeccamycin)

INCHI for NP0014863 (9-methoxyrebeccamycin)

Structure for NP0014863 (9-methoxyrebeccamycin)

3D Structure for NP0014863 (9-methoxyrebeccamycin)