NP-MRD: Showing NP-Card for Ashimide B (NP0019578)

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Record Information

Version

2.0

Created at

2021-01-06 05:04:07 UTC

Updated at

2021-07-15 17:31:21 UTC

NP-MRD ID

NP0019578

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ashimide B

Provided By

NPAtlas

Description

Ashimide B is found in Streptomyces sp. NA03103. Ashimide B was first documented in 2019 (PMID: 30996885). Based on a literature review very few articles have been published on Ashimide B.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120173D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242120173D          

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   -5.8987    3.7543   -0.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9389    2.2703    1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0630   -0.2857    2.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3432   -0.4102    2.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8426    1.2977    2.5099 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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 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
 12 14  1  0  0  0  0
 14 15  2  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  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 23 27  1  0  0  0  0
  9 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 31  2  1  0  0  0  0
 31  6  1  0  0  0  0
 19 14  1  0  0  0  0
 27 18  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  5 37  1  0  0  0  0
  5 38  1  0  0  0  0
  9 39  1  1  0  0  0
 10 40  1  0  0  0  0
 10 41  1  0  0  0  0
 15 42  1  0  0  0  0
 16 43  1  0  0  0  0
 17 44  1  0  0  0  0
 20 45  1  0  0  0  0
 24 46  1  0  0  0  0
 25 47  1  0  0  0  0
 25 48  1  0  0  0  0
 26 49  1  0  0  0  0
 28 50  1  0  0  0  0
 32 51  1  0  0  0  0
 32 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0019578

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@]1(O[H])OC2=C(N([H])C1=O)C(=C([H])C([H])=C2[H])C(=O)OC([H])([H])[C@]1([H])N([H])C(=O)[C@@]2(N(C(=O)C([H])([H])N2C1=O)C([H])([H])[H])C([H])([H])Cl

> <INCHI_IDENTIFIER>
InChI=1S/C19H19ClN4O9/c1-23-12(26)5-24-14(27)10(21-16(29)18(23,24)7-20)6-32-15(28)9-3-2-4-11-13(9)22-17(30)19(31,8-25)33-11/h2-4,10,25,31H,5-8H2,1H3,(H,21,29)(H,22,30)/t10-,18+,19-/m0/s1

> <INCHI_KEY>
KPJFZDGJKLVKPY-XBAUIOEMSA-N

> <FORMULA>
C19H19ClN4O9

> <MOLECULAR_WEIGHT>
482.83

> <EXACT_MASS>
482.0840559

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
43.88535350459052

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(6S,8aS)-8a-(chloromethyl)-1-methyl-2,5,8-trioxo-octahydroimidazo[1,2-a]pyrazin-6-yl]methyl (2S)-2-hydroxy-2-(hydroxymethyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-5-carboxylate

> <ALOGPS_LOGP>
-0.53

> <JCHEM_LOGP>
-0.5780875109999997

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.651641606868838

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.890231698646307

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5145405921953206

> <JCHEM_POLAR_SURFACE_AREA>
174.81

> <JCHEM_REFRACTIVITY>
108.7803

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.19e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(6S,8aS)-8a-(chloromethyl)-1-methyl-2,5,8-trioxo-dihydro-3H-imidazo[1,2-a]pyrazin-6-yl]methyl (2S)-2-hydroxy-2-(hydroxymethyl)-3-oxo-4H-1,4-benzoxazine-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    4.4390    2.6599   -0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6974    1.2504   -0.1551 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6523    0.5300   -0.9033 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7127    0.9693   -1.4478 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2309   -0.8673   -0.9696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2318   -0.9721    0.1053 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4864   -2.0632    0.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9857   -3.1978    0.7516 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0399   -1.8592    0.9710 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2823   -2.2751   -0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0932   -2.2389   -0.2243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9228   -1.1323   -0.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3584   -0.0334   -0.1086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3957   -1.3401   -0.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8539   -2.6622   -0.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1969   -2.8895   -0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0911   -1.8518   -0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6608   -0.5285    0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2837   -0.3227   -0.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8657    1.0381    0.0231 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8776    2.0419    0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5849    3.1355    0.6616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2021    1.7510   -0.4614 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0751    1.5836   -1.8379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2143    2.8295   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3026    2.9560    1.2378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5946    0.4984    0.0806 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8074   -0.5217    1.3888 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6153    0.5742    0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1185    1.6930    0.6295 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0500    0.3257    0.7150 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7936    0.3071    2.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4614   -0.2010    1.6872 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.3978    3.2338   -0.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8295    2.9113   -1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9876    3.0988    0.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8065   -1.0471   -1.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0538   -1.5940   -0.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7829   -2.5171    1.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5486   -3.3796   -0.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7154   -1.7141   -1.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1504   -3.4637   -0.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5623   -3.9196   -0.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1522   -2.0634   -0.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8644    1.2978    0.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6362    0.8620   -2.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1989    2.4818   -0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8987    3.7543   -0.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9389    2.2703    1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0630   -0.2857    2.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3432   -0.4102    2.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8426    1.2977    2.5099 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
  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  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 23 27  1  0
  9 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  1
 32 33  1  0
 31  2  1  0
 31  6  1  0
 19 14  1  0
 27 18  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  0
  5 38  1  0
  9 39  1  1
 10 40  1  0
 10 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 20 45  1  0
 24 46  1  0
 25 47  1  0
 25 48  1  0
 26 49  1  0
 28 50  1  0
 32 51  1  0
 32 52  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       4.439   2.660  -0.263  0.00  0.00           C+0
HETATM    2  N   UNK     0       4.697   1.250  -0.155  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.652   0.530  -0.903  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.713   0.969  -1.448  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.231  -0.867  -0.970  0.00  0.00           C+0
HETATM    6  N   UNK     0       4.232  -0.972   0.105  0.00  0.00           N+0
HETATM    7  C   UNK     0       3.486  -2.063   0.604  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.986  -3.198   0.752  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.040  -1.859   0.971  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.282  -2.275  -0.254  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.093  -2.239  -0.224  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.923  -1.132  -0.145  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.358  -0.033  -0.109  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.396  -1.340  -0.109  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.854  -2.662  -0.158  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.197  -2.890  -0.128  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.091  -1.852  -0.049  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.661  -0.529   0.002  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.284  -0.323  -0.031  0.00  0.00           C+0
HETATM   20  N   UNK     0      -2.866   1.038   0.023  0.00  0.00           N+0
HETATM   21  C   UNK     0      -3.878   2.042   0.105  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.585   3.135   0.662  0.00  0.00           O+0
HETATM   23  C   UNK     0      -5.202   1.751  -0.461  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.075   1.584  -1.838  0.00  0.00           O+0
HETATM   25  C   UNK     0      -6.214   2.829  -0.141  0.00  0.00           C+0
HETATM   26  O   UNK     0      -6.303   2.956   1.238  0.00  0.00           O+0
HETATM   27  O   UNK     0      -5.595   0.498   0.081  0.00  0.00           O+0
HETATM   28  N   UNK     0       1.807  -0.522   1.389  0.00  0.00           N+0
HETATM   29  C   UNK     0       2.615   0.574   0.895  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.119   1.693   0.630  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.050   0.326   0.715  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.794   0.307   2.044  0.00  0.00           C+0
HETATM   33 Cl   UNK     0       6.461  -0.201   1.687  0.00  0.00          Cl+0
HETATM   34  H   UNK     0       5.398   3.234  -0.414  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.829   2.911  -1.175  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.988   3.099   0.651  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.806  -1.047  -1.970  0.00  0.00           H+0
HETATM   38  H   UNK     0       6.054  -1.594  -0.826  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.783  -2.517   1.840  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.549  -3.380  -0.389  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.715  -1.714  -1.132  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.150  -3.464  -0.219  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.562  -3.920  -0.166  0.00  0.00           H+0
HETATM   44  H   UNK     0      -6.152  -2.063  -0.026  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.864   1.298   0.005  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.636   0.862  -2.184  0.00  0.00           H+0
HETATM   47  H   UNK     0      -7.199   2.482  -0.539  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.899   3.754  -0.640  0.00  0.00           H+0
HETATM   49  H   UNK     0      -6.939   2.270   1.553  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.063  -0.286   2.077  0.00  0.00           H+0
HETATM   51  H   UNK     0       4.343  -0.410   2.754  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.843   1.298   2.510  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    1    3   31                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   37   38                                             
CONECT    6    5    7   31                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   28   39                                             
CONECT   10    9   11   40   41                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16   42                                                  
CONECT   16   15   17   43                                                  
CONECT   17   16   18   44                                                  
CONECT   18   17   19   27                                                  
CONECT   19   18   20   14                                                  
CONECT   20   19   21   45                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25   27                                             
CONECT   24   23   46                                                       
CONECT   25   23   26   47   48                                             
CONECT   26   25   49                                                       
CONECT   27   23   18                                                       
CONECT   28    9   29   50                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32    2    6                                             
CONECT   32   31   33   51   52                                             
CONECT   33   32                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    5                                                            
CONECT   38    5                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   10                                                            
CONECT   42   15                                                            
CONECT   43   16                                                            
CONECT   44   17                                                            
CONECT   45   20                                                            
CONECT   46   24                                                            
CONECT   47   25                                                            
CONECT   48   25                                                            
CONECT   49   26                                                            
CONECT   50   28                                                            
CONECT   51   32                                                            
CONECT   52   32                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  110    0
END

RDKit          3D

52 55  0  0  0  0  0  0  0  0999 V2000
    4.4390    2.6599   -0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6974    1.2504   -0.1551 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6523    0.5300   -0.9033 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7127    0.9693   -1.4478 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2309   -0.8673   -0.9696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2318   -0.9721    0.1053 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4864   -2.0632    0.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9857   -3.1978    0.7516 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0399   -1.8592    0.9710 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2823   -2.2751   -0.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0932   -2.2389   -0.2243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9228   -1.1323   -0.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3584   -0.0334   -0.1086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3957   -1.3401   -0.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8539   -2.6622   -0.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1969   -2.8895   -0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0911   -1.8518   -0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6608   -0.5285    0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2837   -0.3227   -0.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8657    1.0381    0.0231 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8776    2.0419    0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5849    3.1355    0.6616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2021    1.7510   -0.4614 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0751    1.5836   -1.8379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2143    2.8295   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3026    2.9560    1.2378 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5946    0.4984    0.0806 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8074   -0.5217    1.3888 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6153    0.5742    0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1185    1.6930    0.6295 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0500    0.3257    0.7150 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7936    0.3071    2.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4614   -0.2010    1.6872 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.3978    3.2338   -0.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8295    2.9113   -1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9876    3.0988    0.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8065   -1.0471   -1.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0538   -1.5940   -0.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7829   -2.5171    1.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5486   -3.3796   -0.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7154   -1.7141   -1.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1504   -3.4637   -0.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5623   -3.9196   -0.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1522   -2.0634   -0.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8644    1.2978    0.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6362    0.8620   -2.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1989    2.4818   -0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8987    3.7543   -0.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9389    2.2703    1.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0630   -0.2857    2.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3432   -0.4102    2.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8426    1.2977    2.5099 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
  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
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 12 14  1  0
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 15 16  1  0
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 20 21  1  0
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 21 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 23 27  1  0
  9 28  1  0
 28 29  1  0
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 31 32  1  1
 32 33  1  0
 31  2  1  0
 31  6  1  0
 19 14  1  0
 27 18  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  0
  5 38  1  0
  9 39  1  1
 10 40  1  0
 10 41  1  0
 15 42  1  0
 16 43  1  0
 17 44  1  0
 20 45  1  0
 24 46  1  0
 25 47  1  0
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 26 49  1  0
 28 50  1  0
 32 51  1  0
 32 52  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
[(6S,8AS)-8a-(chloromethyl)-8-hydroxy-1-methyl-2,5-dioxo-1H,2H,3H,5H,6H,8ah-imidazo[1,2-a]pyrazin-6-yl]methyl 2,3-dihydroxy-2-(hydroxymethyl)-2H-1,4-benzoxazine-5-carboxylic acid	Generator

Chemical Formula

C₁₉H₁₉ClN₄O₉

Average Mass

482.8300 Da

Monoisotopic Mass

482.08406 Da

IUPAC Name

[(6S,8aS)-8a-(chloromethyl)-1-methyl-2,5,8-trioxo-octahydroimidazo[1,2-a]pyrazin-6-yl]methyl (2S)-2-hydroxy-2-(hydroxymethyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-5-carboxylate

Traditional Name

[(6S,8aS)-8a-(chloromethyl)-1-methyl-2,5,8-trioxo-dihydro-3H-imidazo[1,2-a]pyrazin-6-yl]methyl (2S)-2-hydroxy-2-(hydroxymethyl)-3-oxo-4H-1,4-benzoxazine-5-carboxylate

CAS Registry Number

Not Available

SMILES

CN1C(=O)CN2C(=O)[C@H](COC(=O)C3=C4NC(=O)C(O)(CO)OC4=CC=C3)NC(=O)[C@]12CCl

InChI Identifier

InChI=1S/C19H19ClN4O9/c1-23-12(26)5-24-14(27)10(21-16(29)18(23,24)7-20)6-32-15(28)9-3-2-4-11-13(9)22-17(30)19(31,8-25)33-11/h2-4,10,25,31H,5-8H2,1H3,(H,21,29)(H,22,30)/t10-,18+,19?/m0/s1

InChI Key

KPJFZDGJKLVKPY-XBAUIOEMSA-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 sp. NA03103	NPAtlas	30996885

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	-0.53	ALOGPS
logP	-0.58	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	8.89	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	174.81 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	108.78 m³·mol⁻¹	ChemAxon
Polarizability	43.89 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA026370

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

73930446

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

146682816

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shi J, Zeng YJ, Zhang B, Shao FL, Chen YC, Xu X, Sun Y, Xu Q, Tan RX, Ge HM: Comparative genome mining and heterologous expression of an orphan NRPS gene cluster direct the production of ashimides. Chem Sci. 2019 Jan 21;10(10):3042-3048. doi: 10.1039/c8sc05670f. eCollection 2019 Mar 14. [PubMed:30996885 ]

Showing NP-Card for Ashimide B (NP0019578)

MOL for NP0019578 (Ashimide B)

3D MOL for NP0019578 (Ashimide B)

3D SDF for NP0019578 (Ashimide B)

3D-SDF for NP0019578 (Ashimide B)

PDB for NP0019578 (Ashimide B)

3D PDB for NP0019578 (Ashimide B)

SMILES for NP0019578 (Ashimide B)

INCHI for NP0019578 (Ashimide B)

Structure for NP0019578 (Ashimide B)

3D Structure for NP0019578 (Ashimide B)