NP-MRD: Showing NP-Card for Pyranonigrin E (NP0012162)

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Record Information

Version

2.0

Created at

2021-01-05 21:37:42 UTC

Updated at

2021-07-15 17:11:00 UTC

NP-MRD ID

NP0012162

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pyranonigrin E

Provided By

NPAtlas

Description

Pyranonigrin E 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. Pyranonigrin E is found in Aspergillus niger ATCC 1015. Pyranonigrin E was first documented in 2013 (PMID: 24106156). Based on a literature review a small amount of articles have been published on Pyranonigrin E (PMID: 24084681) (PMID: 34459930) (PMID: 33356862).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117023D          

 44 45  0  0  0  0            999 V2000
    4.1886   -2.1681   -1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7283   -1.1606   -0.6901 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9887    0.0064   -0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292    0.3514   -0.1841 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3006    1.4565    0.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8614    1.8014    0.3093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0082    0.9992   -0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3191    0.5559   -0.9160 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5835   -0.2284   -0.2947 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0575    0.1673   -0.4106 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -6.7254   -2.2113   -0.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1694    2.3025    0.9745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167    3.5017    1.5823 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5107    1.9754    1.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3715    2.7036    1.5664 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9432    0.7988    0.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2611    0.1789    0.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3373    0.6463    0.7516 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1166   -1.0428   -0.3920 N   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
    4.1886   -2.1681   -1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7283   -1.1606   -0.6901 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9887    0.0064   -0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292    0.3514   -0.1841 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3006    1.4565    0.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8614    1.8014    0.3093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0082    0.9992   -0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4425    1.3341   -0.3364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3191    0.5559   -0.9160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7686    0.8676   -0.9854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5835   -0.2284   -0.2947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0575    0.1673   -0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9327   -0.8786    0.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7254   -2.2113   -0.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1694    2.3025    0.9745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167    3.5017    1.5823 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5107    1.9754    1.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3715    2.7036    1.5664 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9432    0.7988    0.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2611    0.1789    0.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3373    0.6463    0.7516 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1166   -1.0428   -0.3920 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1814   -1.9889   -0.7398 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1269   -2.1627   -1.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7494   -3.0091   -1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9610    1.8288   -0.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3882   -1.1507   -0.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3173    0.2048   -1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9843   -0.5765    0.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  3
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M  END


  Mrv1652306242117023D          

 44 45  0  0  0  0            999 V2000
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    4.7283   -1.1606   -0.6901 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3006    1.4565    0.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.7254   -2.2113   -0.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5107    1.9754    1.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9432    0.7988    0.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2611    0.1789    0.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
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 23 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0012162

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC2=C(C(=O)N(C2=C([H])[H])C([H])([H])[H])C1=O)C(\[H])=C(/[H])\C(\[H])=C(/[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H21NO4/c1-4-5-6-7-8-9-10-11-13-15(20)16(21)14-17(23-13)12(2)19(3)18(14)22/h8-11,20H,2,4-7H2,1,3H3/b9-8+,11-10+

> <INCHI_KEY>
ITJJIMKGOLMIJY-BNFZFUHLSA-N

> <FORMULA>
C18H21NO4

> <MOLECULAR_WEIGHT>
315.369

> <EXACT_MASS>
315.14705816

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
35.6872152849731

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-6-methyl-7-methylidene-2-[(1E,3E)-nona-1,3-dien-1-yl]-4H,5H,6H,7H-pyrano[2,3-c]pyrrole-4,5-dione

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
2.7345933559999995

> <ALOGPS_LOGS>
-4.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.11624176735213

> <JCHEM_PKA_STRONGEST_BASIC>
-3.740815850960204

> <JCHEM_POLAR_SURFACE_AREA>
66.84

> <JCHEM_REFRACTIVITY>
94.08629999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-6-methyl-7-methylidene-2-[(1E,3E)-nona-1,3-dien-1-yl]pyrano[2,3-c]pyrrole-4,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
    4.1886   -2.1681   -1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7283   -1.1606   -0.6901 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9887    0.0064   -0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292    0.3514   -0.1841 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3006    1.4565    0.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8614    1.8014    0.3093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0082    0.9992   -0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4425    1.3341   -0.3364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3191    0.5559   -0.9160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7686    0.8676   -0.9854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5835   -0.2284   -0.2947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0575    0.1673   -0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9327   -0.8786    0.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7254   -2.2113   -0.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1694    2.3025    0.9745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167    3.5017    1.5823 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5107    1.9754    1.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3715    2.7036    1.5664 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9432    0.7988    0.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2611    0.1789    0.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3373    0.6463    0.7516 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1166   -1.0428   -0.3920 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1814   -1.9889   -0.7398 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1269   -2.1627   -1.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7494   -3.0091   -1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4745    2.7021    0.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3796    0.0916   -0.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7782    2.2527    0.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9311   -0.3666   -1.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0614    0.8387   -2.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9610    1.8288   -0.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2952   -0.3617    0.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3882   -1.1507   -0.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2246    1.1690    0.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3173    0.2048   -1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9843   -0.5765    0.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7012   -0.9369    1.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7000   -2.6032   -0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5034   -2.9432   -0.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7932   -2.0483   -1.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8747    3.8226    1.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7796   -2.9958   -0.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7517   -1.6724   -1.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8356   -2.0518    0.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  5 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 22  2  1  0
 19  3  2  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 16 41  1  0
 23 42  1  0
 23 43  1  0
 23 44  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       4.189  -2.168  -1.341  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.728  -1.161  -0.690  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.989   0.006  -0.165  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.729   0.351  -0.184  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.301   1.456   0.359  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.861   1.801   0.309  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.008   0.999  -0.282  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.442   1.334  -0.336  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.319   0.556  -0.916  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.769   0.868  -0.985  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.583  -0.228  -0.295  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.058   0.167  -0.411  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.933  -0.879   0.256  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.725  -2.211  -0.415  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.169   2.303   0.975  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.817   3.502   1.582  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.511   1.975   1.017  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.372   2.704   1.566  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.943   0.799   0.436  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.261   0.179   0.312  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.337   0.646   0.752  0.00  0.00           O+0
HETATM   22  N   UNK     0       6.117  -1.043  -0.392  0.00  0.00           N+0
HETATM   23  C   UNK     0       7.181  -1.989  -0.740  0.00  0.00           C+0
HETATM   24  H   UNK     0       3.127  -2.163  -1.516  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.749  -3.009  -1.714  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.475   2.702   0.745  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.380   0.092  -0.722  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.778   2.253   0.118  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.931  -0.367  -1.364  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.061   0.839  -2.060  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.961   1.829  -0.505  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.295  -0.362   0.753  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.388  -1.151  -0.873  0.00  0.00           H+0
HETATM   34  H   UNK     0      -6.225   1.169   0.009  0.00  0.00           H+0
HETATM   35  H   UNK     0      -6.317   0.205  -1.488  0.00  0.00           H+0
HETATM   36  H   UNK     0      -7.984  -0.577   0.131  0.00  0.00           H+0
HETATM   37  H   UNK     0      -6.701  -0.937   1.343  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.700  -2.603  -0.210  0.00  0.00           H+0
HETATM   39  H   UNK     0      -7.503  -2.943  -0.152  0.00  0.00           H+0
HETATM   40  H   UNK     0      -6.793  -2.048  -1.512  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.875   3.823   1.603  0.00  0.00           H+0
HETATM   42  H   UNK     0       6.780  -2.996  -0.926  0.00  0.00           H+0
HETATM   43  H   UNK     0       7.752  -1.672  -1.613  0.00  0.00           H+0
HETATM   44  H   UNK     0       7.836  -2.052   0.151  0.00  0.00           H+0
CONECT    1    2   24   25                                                  
CONECT    2    1    3   22                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7   26                                                  
CONECT    7    6    8   27                                                  
CONECT    8    7    9   28                                                  
CONECT    9    8   10   29                                                  
CONECT   10    9   11   30   31                                             
CONECT   11   10   12   32   33                                             
CONECT   12   11   13   34   35                                             
CONECT   13   12   14   36   37                                             
CONECT   14   13   38   39   40                                             
CONECT   15    5   16   17                                                  
CONECT   16   15   41                                                       
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20    3                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23    2                                                  
CONECT   23   22   42   43   44                                             
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    6                                                            
CONECT   27    7                                                            
CONECT   28    8                                                            
CONECT   29    9                                                            
CONECT   30   10                                                            
CONECT   31   10                                                            
CONECT   32   11                                                            
CONECT   33   11                                                            
CONECT   34   12                                                            
CONECT   35   12                                                            
CONECT   36   13                                                            
CONECT   37   13                                                            
CONECT   38   14                                                            
CONECT   39   14                                                            
CONECT   40   14                                                            
CONECT   41   16                                                            
CONECT   42   23                                                            
CONECT   43   23                                                            
CONECT   44   23                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   90    0
END

RDKit          3D

44 45  0  0  0  0  0  0  0  0999 V2000
    4.1886   -2.1681   -1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7283   -1.1606   -0.6901 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9887    0.0064   -0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292    0.3514   -0.1841 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3006    1.4565    0.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8614    1.8014    0.3093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0082    0.9992   -0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4425    1.3341   -0.3364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3191    0.5559   -0.9160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7686    0.8676   -0.9854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5835   -0.2284   -0.2947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0575    0.1673   -0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9327   -0.8786    0.2562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7254   -2.2113   -0.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1694    2.3025    0.9745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167    3.5017    1.5823 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5107    1.9754    1.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3715    2.7036    1.5664 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9432    0.7988    0.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2611    0.1789    0.3115 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3373    0.6463    0.7516 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1166   -1.0428   -0.3920 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1814   -1.9889   -0.7398 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1269   -2.1627   -1.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7494   -3.0091   -1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4745    2.7021    0.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3796    0.0916   -0.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7782    2.2527    0.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9311   -0.3666   -1.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0614    0.8387   -2.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9610    1.8288   -0.5051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2952   -0.3617    0.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3882   -1.1507   -0.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2246    1.1690    0.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3173    0.2048   -1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9843   -0.5765    0.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7012   -0.9369    1.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7000   -2.6032   -0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5034   -2.9432   -0.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7932   -2.0483   -1.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8747    3.8226    1.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7796   -2.9958   -0.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7517   -1.6724   -1.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8356   -2.0518    0.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  5 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 22  2  1  0
 19  3  2  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 16 41  1  0
 23 42  1  0
 23 43  1  0
 23 44  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₈H₂₁NO₄

Average Mass

315.3690 Da

Monoisotopic Mass

315.14706 Da

IUPAC Name

3-hydroxy-6-methyl-7-methylidene-2-[(1E,3E)-nona-1,3-dien-1-yl]-4H,5H,6H,7H-pyrano[2,3-c]pyrrole-4,5-dione

Traditional Name

3-hydroxy-6-methyl-7-methylidene-2-[(1E,3E)-nona-1,3-dien-1-yl]pyrano[2,3-c]pyrrole-4,5-dione

CAS Registry Number

Not Available

SMILES

CCCCC\C=C\C=C\C1=C(O)C(=O)C2=C(O1)C(=C)N(C)C2=O

InChI Identifier

InChI=1S/C18H21NO4/c1-4-5-6-7-8-9-10-11-13-15(20)16(21)14-17(23-13)12(2)19(3)18(14)22/h8-11,20H,2,4-7H2,1,3H3/b9-8+,11-10+

InChI Key

ITJJIMKGOLMIJY-BNFZFUHLSA-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
Aspergillus niger ATCC 1015	NPAtlas	24106156

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	3.4	ALOGPS
logP	2.73	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.12	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.84 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	94.09 m³·mol⁻¹	ChemAxon
Polarizability	35.69 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA013692

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58827644

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102128928

PDB ID

Not Available

ChEBI ID

133787

Good Scents ID

Not Available

References

General References

Awakawa T, Yang XL, Wakimoto T, Abe I: Pyranonigrin E: a PKS-NRPS hybrid metabolite from Aspergillus niger identified by genome mining. Chembiochem. 2013 Nov 4;14(16):2095-9. doi: 10.1002/cbic.201300430. Epub 2013 Sep 17. [PubMed:24106156 ]
Riko R, Nakamura H, Shindo K: Studies on pyranonigrins-isolation of pyranonigrin E and biosynthetic studies on pyranonigrin A. J Antibiot (Tokyo). 2014 Feb;67(2):179-81. doi: 10.1038/ja.2013.91. Epub 2013 Oct 2. [PubMed:24084681 ]
Du X, Li H, Qi J, Chen C, Lu Y, Wang Y: Genome mining of secondary metabolites from a marine-derived Aspergillus terreus B12. Arch Microbiol. 2021 Nov;203(9):5621-5633. doi: 10.1007/s00203-021-02548-4. Epub 2021 Aug 30. [PubMed:34459930 ]
Gao Y, Du X, Li H, Wang Y: Genome sequence of Aspergillus flavus A7, a marine-derived fungus with antibacterial activity. Genome. 2021 Jul;64(7):719-733. doi: 10.1139/gen-2020-0066. Epub 2020 Dec 23. [PubMed:33356862 ]

Showing NP-Card for Pyranonigrin E (NP0012162)

MOL for NP0012162 (Pyranonigrin E)

3D MOL for NP0012162 (Pyranonigrin E)

3D SDF for NP0012162 (Pyranonigrin E)

3D-SDF for NP0012162 (Pyranonigrin E)

PDB for NP0012162 (Pyranonigrin E)

3D PDB for NP0012162 (Pyranonigrin E)

SMILES for NP0012162 (Pyranonigrin E)

INCHI for NP0012162 (Pyranonigrin E)

Structure for NP0012162 (Pyranonigrin E)

3D Structure for NP0012162 (Pyranonigrin E)