NP-MRD: Showing NP-Card for 17-acetoxy-N-(O-methyl)septoriamycin A (NP0010782)

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Record Information

Version

2.0

Created at

2021-01-05 20:37:40 UTC

Updated at

2021-07-15 17:07:04 UTC

NP-MRD ID

NP0010782

Secondary Accession Numbers

None

Natural Product Identification

Common Name

17-acetoxy-N-(O-methyl)septoriamycin A

Provided By

NPAtlas

Description

17-acetoxy-N-(O-methyl)septoriamycin A is found in Septoria and Septoria pistaciarum. 17-acetoxy-N-(O-methyl)septoriamycin A was first documented in 2012 (PMID: 22530813). Based on a literature review very few articles have been published on (2S)-2-[(2S,3S,5R,6R)-6-(4-hydroxy-1-methoxy-2-oxo-5-phenyl-1,2-dihydropyridin-3-yl)-3,5-dimethyloxan-2-yl]butyl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107413D          

 65 67  0  0  0  0            999 V2000
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   -3.9949    1.3400    0.2621 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.6327   -0.0961    3.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2687   -0.0980    4.5955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999    0.4061    3.1177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7441    0.7620   -0.8561 C   0  0  1  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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M  END

     RDKit          3D

 65 67  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242107413D          

 65 67  0  0  0  0            999 V2000
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    0.8970    1.0232    0.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1115    0.2275    0.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5453    1.0446    1.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2301    0.4160    2.6690 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6807    1.1156    3.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4737    2.4734    3.8903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7865    3.1075    2.8500 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3435    2.3925    1.7604 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0413   -0.6214   -0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6776   -1.3843   -1.1365 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5966   -2.2397   -1.7696 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3952   -3.6295   -1.5112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4144   -1.4092   -1.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2009   -2.1871   -2.6339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7427   -1.4159   -2.2289 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.1515    1.2302    1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4124   -1.3971    0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6977    0.5530    5.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3224    0.1770    4.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2233   -1.1850    4.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3081    1.8204   -0.7623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1639    0.4922   -2.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9784    1.6316    1.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3978   -0.6684    2.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2070    0.5762    4.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7997    3.0653    4.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6086    4.1883    2.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8369    2.9562    0.9899 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0589   -0.6321    0.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3589   -3.8537   -1.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0448   -3.9218   -0.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6008   -4.2320   -2.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4383   -1.9612   -1.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4024   -2.7929   -3.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1011   -2.0718   -4.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0058   -3.4128   -2.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2283   -0.2932   -3.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5703   -1.2423   -3.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3417    0.6674   -2.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1531    2.5112   -2.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6041    2.4814   -3.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1753    1.5840   -3.9280 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
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  3  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
 13 14  1  0  0  0  0
 13 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  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 11 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31  9  1  0  0  0  0
 26 12  1  0  0  0  0
 21 16  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  2 36  1  0  0  0  0
  2 37  1  0  0  0  0
  3 38  1  1  0  0  0
  4 39  1  0  0  0  0
  4 40  1  0  0  0  0
  7 41  1  0  0  0  0
  7 42  1  0  0  0  0
  7 43  1  0  0  0  0
  9 44  1  6  0  0  0
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 31 62  1  1  0  0  0
 32 63  1  0  0  0  0
 32 64  1  0  0  0  0
 32 65  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0010782

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C(=O)N(OC([H])([H])[H])C([H])=C1C1=C([H])C([H])=C([H])C([H])=C1[H])[C@]1([H])O[C@]([H])([C@]([H])(C([H])([H])OC(=O)C([H])([H])[H])C([H])([H])C([H])([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])[C@@]1([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H33NO6/c1-6-18(14-31-17(4)27)23-15(2)12-16(3)24(32-23)21-22(28)20(13-26(30-5)25(21)29)19-10-8-7-9-11-19/h7-11,13,15-16,18,23-24,28H,6,12,14H2,1-5H3/t15-,16+,18-,23-,24+/m0/s1

> <INCHI_KEY>
HUJYPQDJLWLYGI-VWCPFRDSSA-N

> <FORMULA>
C25H33NO6

> <MOLECULAR_WEIGHT>
443.54

> <EXACT_MASS>
443.230787787

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
48.830749402080556

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-[(2S,3S,5R,6R)-6-(4-hydroxy-1-methoxy-2-oxo-5-phenyl-1,2-dihydropyridin-3-yl)-3,5-dimethyloxan-2-yl]butyl acetate

> <ALOGPS_LOGP>
3.62

> <JCHEM_LOGP>
3.7011530309999987

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.35678178511091

> <JCHEM_PKA_STRONGEST_BASIC>
-4.101293090484098

> <JCHEM_POLAR_SURFACE_AREA>
85.30000000000001

> <JCHEM_REFRACTIVITY>
121.19670000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.80e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(2S,3S,5R,6R)-6-(4-hydroxy-1-methoxy-2-oxo-5-phenylpyridin-3-yl)-3,5-dimethyloxan-2-yl]butyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 65 67  0  0  0  0  0  0  0  0999 V2000
   -5.0651    0.6292   -0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0413   -0.6214   -0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3978   -0.6684    2.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2070    0.5762    4.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6086    4.1883    2.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8369    2.9562    0.9899 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0058   -3.4128   -2.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2283   -0.2932   -3.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1753    1.5840   -3.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  5  6  1  0
  6  7  1  0
  6  8  2  0
  3  9  1  0
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 31  9  1  0
 26 12  1  0
 21 16  1  0
  1 33  1  0
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  1 35  1  0
  2 36  1  0
  2 37  1  0
  3 38  1  1
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 31 62  1  1
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 32 64  1  0
 32 65  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      -5.065   0.629  -0.536  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.995   1.340   0.262  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.680   0.672   0.299  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.847  -0.703   0.885  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.326  -0.648   2.181  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.633  -0.096   3.233  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.269  -0.098   4.596  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.500   0.406   3.118  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.744   0.762  -0.856  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.655  -0.005  -0.462  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.098  -0.465  -1.566  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.461  -0.616  -1.108  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.857   0.205  -0.009  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.897   1.023   0.566  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.111   0.228   0.502  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.545   1.045   1.632  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.230   0.416   2.669  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.681   1.116   3.767  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.474   2.473   3.890  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.787   3.107   2.850  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.344   2.393   1.760  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.041  -0.621  -0.118  0.00  0.00           C+0
HETATM   23  N   UNK     0       3.678  -1.384  -1.137  0.00  0.00           N+0
HETATM   24  O   UNK     0       4.597  -2.240  -1.770  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.395  -3.630  -1.511  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.414  -1.409  -1.652  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.201  -2.187  -2.634  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.743  -1.416  -2.229  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.364  -2.437  -3.212  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.789  -0.536  -3.015  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.222   0.647  -2.223  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.778   1.861  -3.073  0.00  0.00           C+0
HETATM   33  H   UNK     0      -5.426   1.187  -1.410  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.790  -0.397  -0.851  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.992   0.463   0.090  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.952   2.426   0.015  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.375   1.350   1.326  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.151   1.230   1.201  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.788  -1.130   0.914  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.412  -1.397   0.224  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.698   0.553   5.279  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.322   0.177   4.547  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.223  -1.185   4.908  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.308   1.820  -0.762  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.164   0.492  -2.265  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.978   1.632   1.331  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.398  -0.668   2.569  0.00  0.00           H+0
HETATM   48  H   UNK     0       5.207   0.576   4.546  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.800   3.065   4.734  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.609   4.188   2.935  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.837   2.956   0.990  0.00  0.00           H+0
HETATM   52  H   UNK     0       5.059  -0.632   0.260  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.359  -3.854  -1.200  0.00  0.00           H+0
HETATM   54  H   UNK     0       5.045  -3.922  -0.661  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.601  -4.232  -2.425  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.438  -1.961  -1.460  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.402  -2.793  -3.640  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.101  -2.072  -4.142  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.006  -3.413  -2.828  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.228  -0.293  -3.944  0.00  0.00           H+0
HETATM   61  H   UNK     0      -2.570  -1.242  -3.295  0.00  0.00           H+0
HETATM   62  H   UNK     0      -3.342   0.667  -2.359  0.00  0.00           H+0
HETATM   63  H   UNK     0      -1.153   2.511  -2.399  0.00  0.00           H+0
HETATM   64  H   UNK     0      -2.604   2.481  -3.401  0.00  0.00           H+0
HETATM   65  H   UNK     0      -1.175   1.584  -3.928  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    1    3   36   37                                             
CONECT    3    2    4    9   38                                             
CONECT    4    3    5   39   40                                             
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6   41   42   43                                             
CONECT    8    6                                                            
CONECT    9    3   10   31   44                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   28   45                                             
CONECT   12   11   13   26                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13   46                                                       
CONECT   15   13   16   22                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18   47                                                  
CONECT   18   17   19   48                                                  
CONECT   19   18   20   49                                                  
CONECT   20   19   21   50                                                  
CONECT   21   20   16   51                                                  
CONECT   22   15   23   52                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24   53   54   55                                             
CONECT   26   23   27   12                                                  
CONECT   27   26                                                            
CONECT   28   11   29   30   56                                             
CONECT   29   28   57   58   59                                             
CONECT   30   28   31   60   61                                             
CONECT   31   30   32    9   62                                             
CONECT   32   31   63   64   65                                             
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    2                                                            
CONECT   37    2                                                            
CONECT   38    3                                                            
CONECT   39    4                                                            
CONECT   40    4                                                            
CONECT   41    7                                                            
CONECT   42    7                                                            
CONECT   43    7                                                            
CONECT   44    9                                                            
CONECT   45   11                                                            
CONECT   46   14                                                            
CONECT   47   17                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   21                                                            
CONECT   52   22                                                            
CONECT   53   25                                                            
CONECT   54   25                                                            
CONECT   55   25                                                            
CONECT   56   28                                                            
CONECT   57   29                                                            
CONECT   58   29                                                            
CONECT   59   29                                                            
CONECT   60   30                                                            
CONECT   61   30                                                            
CONECT   62   31                                                            
CONECT   63   32                                                            
CONECT   64   32                                                            
CONECT   65   32                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  134    0
END

RDKit          3D

65 67  0  0  0  0  0  0  0  0999 V2000
   -5.0651    0.6292   -0.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9949    1.3400    0.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6801    0.6722    0.2986 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8471   -0.7030    0.8847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3263   -0.6482    2.1813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6327   -0.0961    3.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2687   -0.0980    4.5955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999    0.4061    3.1177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7441    0.7620   -0.8561 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6552   -0.0054   -0.4623 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0982   -0.4648   -1.5658 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4611   -0.6164   -1.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8571    0.2051   -0.0086 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8970    1.0232    0.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1115    0.2275    0.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5453    1.0446    1.6323 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2301    0.4160    2.6690 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6807    1.1156    3.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4737    2.4734    3.8903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7865    3.1075    2.8500 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3435    2.3925    1.7604 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0413   -0.6214   -0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6776   -1.3843   -1.1365 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5966   -2.2397   -1.7696 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3952   -3.6295   -1.5112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4144   -1.4092   -1.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2009   -2.1871   -2.6339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7427   -1.4159   -2.2289 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3637   -2.4370   -3.2120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7889   -0.5361   -3.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2222    0.6465   -2.2230 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7779    1.8613   -3.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4259    1.1867   -1.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7895   -0.3970   -0.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9917    0.4634    0.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9524    2.4262    0.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3750    1.3503    1.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1515    1.2302    1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7884   -1.1301    0.9142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4124   -1.3971    0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6977    0.5530    5.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3224    0.1770    4.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2233   -1.1850    4.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3081    1.8204   -0.7623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1639    0.4922   -2.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9784    1.6316    1.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3978   -0.6684    2.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2070    0.5762    4.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7997    3.0653    4.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6086    4.1883    2.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8369    2.9562    0.9899 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0589   -0.6321    0.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3589   -3.8537   -1.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0448   -3.9218   -0.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6008   -4.2320   -2.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4383   -1.9612   -1.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4024   -2.7929   -3.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1011   -2.0718   -4.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0058   -3.4128   -2.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2283   -0.2932   -3.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5703   -1.2423   -3.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3417    0.6674   -2.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1531    2.5112   -2.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6041    2.4814   -3.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1753    1.5840   -3.9280 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
  6  7  1  0
  6  8  2  0
  3  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 15 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  2  0
 11 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 31  9  1  0
 26 12  1  0
 21 16  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  3 38  1  1
  4 39  1  0
  4 40  1  0
  7 41  1  0
  7 42  1  0
  7 43  1  0
  9 44  1  6
 11 45  1  6
 14 46  1  0
 17 47  1  0
 18 48  1  0
 19 49  1  0
 20 50  1  0
 21 51  1  0
 22 52  1  0
 25 53  1  0
 25 54  1  0
 25 55  1  0
 28 56  1  1
 29 57  1  0
 29 58  1  0
 29 59  1  0
 30 60  1  0
 30 61  1  0
 31 62  1  1
 32 63  1  0
 32 64  1  0
 32 65  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2S)-2-[(2S,3S,5R,6R)-6-(4-Hydroxy-1-methoxy-2-oxo-5-phenyl-1,2-dihydropyridin-3-yl)-3,5-dimethyloxan-2-yl]butyl acetic acid	Generator

Chemical Formula

C₂₅H₃₃NO₆

Average Mass

443.5400 Da

Monoisotopic Mass

443.23079 Da

IUPAC Name

(2S)-2-[(2S,3S,5R,6R)-6-(4-hydroxy-1-methoxy-2-oxo-5-phenyl-1,2-dihydropyridin-3-yl)-3,5-dimethyloxan-2-yl]butyl acetate

Traditional Name

(2S)-2-[(2S,3S,5R,6R)-6-(4-hydroxy-1-methoxy-2-oxo-5-phenylpyridin-3-yl)-3,5-dimethyloxan-2-yl]butyl acetate

CAS Registry Number

Not Available

SMILES

CC[C@@H](COC(C)=O)[C@H]1O[C@H]([C@H](C)C[C@@H]1C)C1=C(O)C(=CN(OC)C1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C25H33NO6/c1-6-18(14-31-17(4)27)23-15(2)12-16(3)24(32-23)21-22(28)20(13-26(30-5)25(21)29)19-10-8-7-9-11-19/h7-11,13,15-16,18,23-24,28H,6,12,14H2,1-5H3/t15-,16+,18-,23-,24+/m0/s1

InChI Key

HUJYPQDJLWLYGI-VWCPFRDSSA-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
Septoria	NPAtlas	22530813
Septoria pistaciarum	LOTUS Database	35616633

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	3.62	ALOGPS
logP	3.7	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.36	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.3 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	121.2 m³·mol⁻¹	ChemAxon
Polarizability	48.83 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA006313

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78442570

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139584871

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kumarihamy M, Khan SI, Jacob M, Tekwani BL, Duke SO, Ferreira D, Nanayakkara NP: Antiprotozoal and antimicrobial compounds from the plant pathogen Septoria pistaciarum. J Nat Prod. 2012 May 25;75(5):883-9. doi: 10.1021/np200940b. Epub 2012 Apr 24. [PubMed:22530813 ]

Showing NP-Card for 17-acetoxy-N-(O-methyl)septoriamycin A (NP0010782)

MOL for NP0010782 (17-acetoxy-N-(O-methyl)septoriamycin A)

3D MOL for NP0010782 (17-acetoxy-N-(O-methyl)septoriamycin A)

3D SDF for NP0010782 (17-acetoxy-N-(O-methyl)septoriamycin A)

3D-SDF for NP0010782 (17-acetoxy-N-(O-methyl)septoriamycin A)

PDB for NP0010782 (17-acetoxy-N-(O-methyl)septoriamycin A)

3D PDB for NP0010782 (17-acetoxy-N-(O-methyl)septoriamycin A)

SMILES for NP0010782 (17-acetoxy-N-(O-methyl)septoriamycin A)

INCHI for NP0010782 (17-acetoxy-N-(O-methyl)septoriamycin A)

Structure for NP0010782 (17-acetoxy-N-(O-methyl)septoriamycin A)

3D Structure for NP0010782 (17-acetoxy-N-(O-methyl)septoriamycin A)