NP-MRD: Showing NP-Card for Blasticidin S (NP0023790)

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Record Information

Version

1.0

Created at

2021-01-06 08:49:49 UTC

Updated at

2021-07-15 17:42:42 UTC

NP-MRD ID

NP0023790

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Blasticidin S

Provided By

NPAtlas

Description

Blasticidin S is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Blasticidin S is found in Streptomyces arginensis, Streptomyces griseochromogenes and Streptomyces lividans. It was first documented in 1958 (PMID: 13525246). Based on a literature review a significant number of articles have been published on Blasticidin S (PMID: 9711220) (PMID: 23377931) (PMID: 12964155) (PMID: 16659097).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120443D          

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M  END

     RDKit          3D

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  Mrv1652306242120443D          

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   -3.1099    0.1758    1.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2400    3.0664    1.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6826    2.1144    1.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4678    2.3137   -1.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6603    0.8762   -1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7421    2.5308   -0.9560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7762   -0.5045   -0.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6196   -0.1174   -1.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -1.8543   -0.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7647   -0.0539   -0.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626   -1.9247    1.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921   -2.7926    1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3809   -3.0357   -0.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3032    0.4480   -1.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1618    1.9505   -0.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0251    2.3186    1.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9331    0.9499    1.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9003   -2.9124   -1.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2218   -2.5727   -3.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2020    1.1031    0.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7193   -1.7165    0.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8797   -1.7161    2.4064 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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  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  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 24 11  1  0  0  0  0
 21 15  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  3 34  1  0  0  0  0
  3 35  1  0  0  0  0
  4 36  1  0  0  0  0
  4 37  1  0  0  0  0
  5 38  1  6  0  0  0
  6 39  1  0  0  0  0
  6 40  1  0  0  0  0
  7 41  1  0  0  0  0
  7 42  1  0  0  0  0
 10 43  1  0  0  0  0
 11 44  1  1  0  0  0
 12 45  1  0  0  0  0
 13 46  1  0  0  0  0
 14 47  1  6  0  0  0
 16 48  1  0  0  0  0
 17 49  1  0  0  0  0
 19 50  1  0  0  0  0
 19 51  1  0  0  0  0
 24 52  1  1  0  0  0
 27 53  1  0  0  0  0
 29 54  1  0  0  0  0
 30 55  1  0  0  0  0
 30 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0023790

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]1([H])O[C@]([H])(C([H])=C([H])[C@]1([H])N([H])C(=O)C([H])([H])[C@@]([H])(N([H])[H])C([H])([H])C([H])([H])N(C(=N[H])N([H])[H])C([H])([H])[H])N1C([H])=C([H])C(=NC1=O)N([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H26N8O5/c1-24(16(20)21)6-4-9(18)8-12(26)22-10-2-3-13(30-14(10)15(27)28)25-7-5-11(19)23-17(25)29/h2-3,5,7,9-10,13-14H,4,6,8,18H2,1H3,(H3,20,21)(H,22,26)(H,27,28)(H2,19,23,29)/t9-,10-,13+,14-/m0/s1

> <INCHI_KEY>
CXNPLSGKWMLZPZ-ZNIXKSQXSA-N

> <FORMULA>
C17H26N8O5

> <MOLECULAR_WEIGHT>
422.4389

> <EXACT_MASS>
422.202615982

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
41.979400620789335

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,6R)-6-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-[(3S)-3-amino-5-(N-methylcarbamimidamido)pentanamido]-3,6-dihydro-2H-pyran-2-carboxylic acid

> <ALOGPS_LOGP>
-3.28

> <JCHEM_LOGP>
-4.699743939138351

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.51497440665683

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3102993008163746

> <JCHEM_PKA_STRONGEST_BASIC>
12.185436521117454

> <JCHEM_POLAR_SURFACE_AREA>
213.45000000000002

> <JCHEM_REFRACTIVITY>
116.42339999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
blasticidin S

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 57  0  0  0  0  0  0  0  0999 V2000
   -5.6816    2.4278    2.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9057    1.2115    1.8178 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4764    1.2155    1.9937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7433    2.0585    0.9782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9499    1.5682   -0.4373 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3476    1.6080   -0.7356 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3067    0.2541   -0.7267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8461    0.2185   -0.5694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2169    1.2611   -0.3034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1180   -0.9935   -0.7130 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3099   -1.0738   -0.5654 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6968   -1.8112    0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9432   -2.2546    0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9016   -2.0463   -0.4138 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9954   -1.1698    0.0373 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0654    0.1088   -0.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0912    0.9110    0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0522    0.4520    0.9178 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1043    1.3138    1.3637 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9522   -0.8225    1.3328 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9266   -1.5932    0.8797 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8692   -2.7963    1.2998 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3652   -1.5406   -1.5626 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0117   -1.8087   -1.6824 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4806   -1.4898   -3.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2571   -1.0439   -3.8864 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1503   -1.6674   -3.3204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5936    0.0626    1.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7638    0.1732    0.8791 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0181   -1.2276    1.4965 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1946    3.0091    2.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6771    2.1470    2.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8083    3.0218    1.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2895    1.6699    2.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1099    0.1758    1.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2400    3.0664    1.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6826    2.1144    1.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4678    2.3137   -1.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6603    0.8762   -1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7421    2.5308   -0.9560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7762   -0.5045   -0.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6196   -0.1174   -1.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -1.8543   -0.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7647   -0.0539   -0.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626   -1.9247    1.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921   -2.7926    1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3809   -3.0357   -0.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3032    0.4480   -1.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1618    1.9505   -0.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0251    2.3186    1.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9331    0.9499    1.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9003   -2.9124   -1.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2218   -2.5727   -3.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2020    1.1031    0.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7193   -1.7165    0.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8797   -1.7161    2.4064 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  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  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  2  0
 14 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
  2 28  1  0
 28 29  2  0
 28 30  1  0
 24 11  1  0
 21 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  6
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
 10 43  1  0
 11 44  1  1
 12 45  1  0
 13 46  1  0
 14 47  1  6
 16 48  1  0
 17 49  1  0
 19 50  1  0
 19 51  1  0
 24 52  1  1
 27 53  1  0
 29 54  1  0
 30 55  1  0
 30 56  1  0
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      -5.682   2.428   2.087  0.00  0.00           C+0
HETATM    2  N   UNK     0      -4.906   1.212   1.818  0.00  0.00           N+0
HETATM    3  C   UNK     0      -3.476   1.216   1.994  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.743   2.059   0.978  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.950   1.568  -0.437  0.00  0.00           C+0
HETATM    6  N   UNK     0      -4.348   1.608  -0.736  0.00  0.00           N+0
HETATM    7  C   UNK     0      -2.307   0.254  -0.727  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.846   0.219  -0.569  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.217   1.261  -0.303  0.00  0.00           O+0
HETATM   10  N   UNK     0      -0.118  -0.994  -0.713  0.00  0.00           N+0
HETATM   11  C   UNK     0       1.310  -1.074  -0.565  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.697  -1.811   0.682  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.943  -2.255   0.703  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.902  -2.046  -0.414  0.00  0.00           C+0
HETATM   15  N   UNK     0       4.995  -1.170   0.037  0.00  0.00           N+0
HETATM   16  C   UNK     0       5.065   0.109  -0.402  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.091   0.911   0.040  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.052   0.452   0.918  0.00  0.00           C+0
HETATM   19  N   UNK     0       8.104   1.314   1.364  0.00  0.00           N+0
HETATM   20  N   UNK     0       6.952  -0.823   1.333  0.00  0.00           N+0
HETATM   21  C   UNK     0       5.927  -1.593   0.880  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.869  -2.796   1.300  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.365  -1.541  -1.563  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.012  -1.809  -1.682  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.481  -1.490  -3.010  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.257  -1.044  -3.886  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.150  -1.667  -3.320  0.00  0.00           O+0
HETATM   28  C   UNK     0      -5.594   0.063   1.384  0.00  0.00           C+0
HETATM   29  N   UNK     0      -6.764   0.173   0.879  0.00  0.00           N+0
HETATM   30  N   UNK     0      -5.018  -1.228   1.496  0.00  0.00           N+0
HETATM   31  H   UNK     0      -5.195   3.009   2.907  0.00  0.00           H+0
HETATM   32  H   UNK     0      -6.677   2.147   2.475  0.00  0.00           H+0
HETATM   33  H   UNK     0      -5.808   3.022   1.160  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.289   1.670   2.995  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.110   0.176   1.925  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.240   3.066   1.013  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.683   2.114   1.246  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.468   2.314  -1.125  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.660   0.876  -1.411  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.742   2.531  -0.956  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.776  -0.504  -0.030  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.620  -0.117  -1.741  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.638  -1.854  -0.935  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.765  -0.054  -0.457  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.963  -1.925   1.449  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.292  -2.793   1.565  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.381  -3.036  -0.625  0.00  0.00           H+0
HETATM   48  H   UNK     0       4.303   0.448  -1.092  0.00  0.00           H+0
HETATM   49  H   UNK     0       6.162   1.950  -0.307  0.00  0.00           H+0
HETATM   50  H   UNK     0       8.025   2.319   1.171  0.00  0.00           H+0
HETATM   51  H   UNK     0       8.933   0.950   1.868  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.900  -2.912  -1.454  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.222  -2.573  -3.597  0.00  0.00           H+0
HETATM   54  H   UNK     0      -7.202   1.103   0.790  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.719  -1.716   0.630  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.880  -1.716   2.406  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    1    3   28                                                  
CONECT    3    2    4   34   35                                             
CONECT    4    3    5   36   37                                             
CONECT    5    4    6    7   38                                             
CONECT    6    5   39   40                                                  
CONECT    7    5    8   41   42                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   43                                                  
CONECT   11   10   12   24   44                                             
CONECT   12   11   13   45                                                  
CONECT   13   12   14   46                                                  
CONECT   14   13   15   23   47                                             
CONECT   15   14   16   21                                                  
CONECT   16   15   17   48                                                  
CONECT   17   16   18   49                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   50   51                                                  
CONECT   20   18   21                                                       
CONECT   21   20   22   15                                                  
CONECT   22   21                                                            
CONECT   23   14   24                                                       
CONECT   24   23   25   11   52                                             
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   53                                                       
CONECT   28    2   29   30                                                  
CONECT   29   28   54                                                       
CONECT   30   28   55   56                                                  
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    3                                                            
CONECT   35    3                                                            
CONECT   36    4                                                            
CONECT   37    4                                                            
CONECT   38    5                                                            
CONECT   39    6                                                            
CONECT   40    6                                                            
CONECT   41    7                                                            
CONECT   42    7                                                            
CONECT   43   10                                                            
CONECT   44   11                                                            
CONECT   45   12                                                            
CONECT   46   13                                                            
CONECT   47   14                                                            
CONECT   48   16                                                            
CONECT   49   17                                                            
CONECT   50   19                                                            
CONECT   51   19                                                            
CONECT   52   24                                                            
CONECT   53   27                                                            
CONECT   54   29                                                            
CONECT   55   30                                                            
CONECT   56   30                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  114    0
END

RDKit          3D

56 57  0  0  0  0  0  0  0  0999 V2000
   -5.6816    2.4278    2.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9057    1.2115    1.8178 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1180   -0.9935   -0.7130 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3099   -1.0738   -0.5654 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6968   -1.8112    0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9432   -2.2546    0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0522    0.4520    0.9178 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1043    1.3138    1.3637 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9522   -0.8225    1.3328 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9266   -1.5932    0.8797 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8692   -2.7963    1.2998 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3652   -1.5406   -1.5626 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0117   -1.8087   -1.6824 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4806   -1.4898   -3.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2571   -1.0439   -3.8864 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1503   -1.6674   -3.3204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5936    0.0626    1.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7638    0.1732    0.8791 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0181   -1.2276    1.4965 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1946    3.0091    2.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1099    0.1758    1.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2400    3.0664    1.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6826    2.1144    1.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4678    2.3137   -1.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6603    0.8762   -1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7421    2.5308   -0.9560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7762   -0.5045   -0.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6196   -0.1174   -1.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -1.8543   -0.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7647   -0.0539   -0.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626   -1.9247    1.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921   -2.7926    1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3809   -3.0357   -0.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3032    0.4480   -1.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1618    1.9505   -0.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0251    2.3186    1.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9331    0.9499    1.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9003   -2.9124   -1.4544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2218   -2.5727   -3.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2020    1.1031    0.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7193   -1.7165    0.6299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8797   -1.7161    2.4064 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  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
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 14 23  1  0
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  2 28  1  0
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 24 11  1  0
 21 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  6
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
 10 43  1  0
 11 44  1  1
 12 45  1  0
 13 46  1  0
 14 47  1  6
 16 48  1  0
 17 49  1  0
 19 50  1  0
 19 51  1  0
 24 52  1  1
 27 53  1  0
 29 54  1  0
 30 55  1  0
 30 56  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Blasticidin-S	ChEBI
Blasticidin S, carbamodithioate, (S)-isomer	MeSH
Blasticidin S, dodecyl sulfate, (S)-isomer	MeSH
Blasticidin S, hydrochloride, (S)-isomer	MeSH
Blasticidin S, methyl sulfate, (S)-isomer	MeSH
Blasticidin S, monohydrochloride, (S)-isomer	MeSH

Chemical Formula

C₁₇H₂₆N₈O₅

Average Mass

422.4389 Da

Monoisotopic Mass

422.20262 Da

IUPAC Name

(2S,3S,6R)-6-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-[(3S)-3-amino-5-(N-methylcarbamimidamido)pentanamido]-3,6-dihydro-2H-pyran-2-carboxylic acid

Traditional Name

blasticidin S

CAS Registry Number

Not Available

SMILES

CN(CC[C@H](N)CC(=O)N[C@H]1C=C[C@@H](O[C@@H]1C(O)=O)N1C=CC(N)=NC1=O)C(N)=N

InChI Identifier

InChI=1S/C17H26N8O5/c1-24(16(20)21)6-4-9(18)8-12(26)22-10-2-3-13(30-14(10)15(27)28)25-7-5-11(19)23-17(25)29/h2-3,5,7,9-10,13-14H,4,6,8,18H2,1H3,(H3,20,21)(H,22,26)(H,27,28)(H2,19,23,29)/t9-,10-,13+,14-/m0/s1

InChI Key

CXNPLSGKWMLZPZ-ZNIXKSQXSA-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
Streptomyces arginensis	LOTUS Database	35616633
Streptomyces griseochromogenes	NPAtlas	9711220
Streptomyces lividans	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Streptomyces sp. HK1-0052	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Beta amino acids and derivatives

Alternative Parents

Substituents

Beta amino acid or derivatives
Aminopyrimidine
Pyrimidone
Fatty amide
Hydropyrimidine
N-acyl-amine
Pyran
Pyrimidine
Fatty acyl
Imidolactam
Heteroaromatic compound
Carboxamide group
Guanidine
Amino acid
Secondary carboxylic acid amide
Oxacycle
Organoheterocyclic compound
Carboximidamide
Azacycle
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Primary aliphatic amine
Imine
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organonitrogen compound
Amine
Carbonyl group
Organooxygen compound
Organic oxygen compound
Primary amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

antibiotic antifungal agent (CHEBI:15353 )
blasticidin (CHEBI:15353 )

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	-3.3	ALOGPS
logP	-4.7	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	12.19	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	213.45 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	116.42 m³·mol⁻¹	ChemAxon
Polarizability	41.98 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

NPAtlas ID

NPA020580

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00016063

Chemspider ID

148673

KEGG Compound ID

Not Available

BioCyc ID

blasticidin-s

BiGG ID

Not Available

Wikipedia Link

Blasticidin_S

METLIN ID

Not Available

PubChem Compound

170012

PDB ID

Not Available

ChEBI ID

15353

Good Scents ID

Not Available

References

General References

Cone MC, Petrich AK, Gould SJ, Zabriskie TM: Cloning and heterologous expression of blasticidin S biosynthetic genes from Streptomyces griseochromogenes. J Antibiot (Tokyo). 1998 Jun;51(6):570-8. doi: 10.7164/antibiotics.51.570. [PubMed:9711220 ]
Li L, Wu J, Deng Z, Zabriskie TM, He X: Streptomyces lividans blasticidin S deaminase and its application in engineering a blasticidin S-producing strain for ease of genetic manipulation. Appl Environ Microbiol. 2013 Apr;79(7):2349-57. doi: 10.1128/AEM.03254-12. Epub 2013 Feb 1. [PubMed:23377931 ]
Cone MC, Yin X, Grochowski LL, Parker MR, Zabriskie TM: The blasticidin S biosynthesis gene cluster from Streptomyces griseochromogenes: sequence analysis, organization, and initial characterization. Chembiochem. 2003 Sep 5;4(9):821-8. doi: 10.1002/cbic.200300583. [PubMed:12964155 ]
TAKEUCHI S, HIRAYAMA K, UEDA K, SAKAI H, YONEHARA H: Blasticidin S, a new antibiotic. J Antibiot (Tokyo). 1958 Jan;11(1):1-5. [PubMed:13525246 ]
Mory YY, Chen D, Sarid S: De Novo Biosynthesis of Deoxyribonucleic Acid Polymerase during Wheat Embryo Germination. Plant Physiol. 1975 Mar;55(3):437-42. doi: 10.1104/pp.55.3.437. [PubMed:16659097 ]

Showing NP-Card for Blasticidin S (NP0023790)

MOL for NP0023790 (Blasticidin S)

3D MOL for NP0023790 (Blasticidin S)

3D SDF for NP0023790 (Blasticidin S)

3D-SDF for NP0023790 (Blasticidin S)

PDB for NP0023790 (Blasticidin S)

3D PDB for NP0023790 (Blasticidin S)

SMILES for NP0023790 (Blasticidin S)

INCHI for NP0023790 (Blasticidin S)

Structure for NP0023790 (Blasticidin S)

3D Structure for NP0023790 (Blasticidin S)