NP-MRD: Showing NP-Card for Aspergillimide (NP0023578)

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Record Information

Version

2.0

Created at

2021-01-06 08:38:30 UTC

Updated at

2021-07-15 17:42:07 UTC

NP-MRD ID

NP0023578

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aspergillimide

Provided By

NPAtlas

Description

Asperparaline A, also known as aspergillimide, belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom. Asperparaline A 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. Aspergillimide is found in Aspergillus. Aspergillimide was first documented in 1997 (PMID: 9402989). Based on a literature review very few articles have been published on asperparaline A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120433D          

 55 59  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242120433D          

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    0.8221    0.2017   -2.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8109    1.3725   -1.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6144   -0.1681   -1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5241   -2.0402    0.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2365   -1.5287   -1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2230    2.3673   -0.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5099    1.9717    1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1147    2.9612    1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -2.5050   -1.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0114   -2.9764   -0.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5579   -3.4017    0.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6081   -1.3243    2.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5655   -2.7567    2.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9422   -1.2092    2.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0432    0.3337    1.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8007   -0.9160    1.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5930   -2.0675    0.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8452    2.9640   -0.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8288    3.5395   -0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2132    3.0143   -1.7677 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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22  2  1  0  0  0  0
 22  5  1  0  0  0  0
 20  7  1  0  0  0  0
  7 25  1  1  0  0  0
  9 15  1  1  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  2 30  1  1  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
  4 33  1  0  0  0  0
  4 34  1  0  0  0  0
  6 35  1  0  0  0  0
  6 36  1  0  0  0  0
  8 37  1  0  0  0  0
  8 38  1  0  0  0  0
 10 39  1  0  0  0  0
 10 40  1  0  0  0  0
 14 41  1  0  0  0  0
 14 42  1  0  0  0  0
 14 43  1  0  0  0  0
 18 44  1  0  0  0  0
 18 45  1  0  0  0  0
 18 46  1  0  0  0  0
 19 47  1  0  0  0  0
 19 48  1  0  0  0  0
 19 49  1  0  0  0  0
 20 50  1  1  0  0  0
 21 51  1  0  0  0  0
 21 52  1  0  0  0  0
 26 53  1  0  0  0  0
 26 54  1  0  0  0  0
 26 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0023578

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])([H])N1C(=O)C([H])([H])[C@]2(C1=O)C([H])([H])[C@]13N(C(=O)[C@]4(N(C([H])([H])C([H])([H])[C@@]4([H])C([H])([H])[H])C1([H])[H])C([H])([H])[C@]3([H])C2(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H29N3O3/c1-12-6-7-23-11-19-10-18(9-14(24)21(4)15(18)25)17(2,3)13(19)8-20(12,23)16(26)22(19)5/h12-13H,6-11H2,1-5H3/t12-,13-,18-,19+,20+/m1/s1

> <INCHI_KEY>
RTNMRJRMTGSUAE-DWPFRNKMSA-N

> <FORMULA>
C20H29N3O3

> <MOLECULAR_WEIGHT>
359.47

> <EXACT_MASS>
359.220891806

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.91190341806599

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,3R,3'R,7'R,12'R)-1,4',4',12',14'-pentamethyl-9',14'-diazaspiro[pyrrolidine-3,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecane]-2,5,13'-trione

> <ALOGPS_LOGP>
1.40

> <JCHEM_LOGP>
0.4844717876666657

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.64939826217982

> <JCHEM_PKA_STRONGEST_BASIC>
8.828187005356707

> <JCHEM_POLAR_SURFACE_AREA>
60.93000000000001

> <JCHEM_REFRACTIVITY>
96.1568

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.53e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,3R,3'R,7'R,12'R)-1,4',4',12',14'-pentamethyl-9',14'-diazaspiro[pyrrolidine-3,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecane]-2,5,13'-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
    4.4519    0.3244    1.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8242   -0.4582    0.2752 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3789    0.0017   -1.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1543    0.1391   -1.9821 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1877   -0.6505   -1.2942 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8388   -0.4782   -1.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0133    0.2307   -0.6442 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4152    0.3627   -0.9657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1302   -0.4347    0.1026 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3028   -1.1939   -0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3953   -0.1795   -0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5162   -0.2957   -0.8655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9728    0.8945    0.5436 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7403    2.1042    0.7683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7041    0.5182    1.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2706    0.9853    2.1492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0626   -1.3327    0.7407 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0012   -2.5703   -0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5720   -1.6560    2.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1056   -0.4528    0.7172 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4506   -1.0229    0.9300 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3853   -0.1939    0.0924 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0366    1.2554    0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7904    2.1599    0.4983 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7097    1.5051   -0.4246 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1694    2.7830   -0.6815 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6960    0.7011    2.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1075   -0.3623    1.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0994    1.1391    1.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0018   -1.5301    0.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7817    1.0352   -0.9336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1139   -0.7038   -1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3723   -0.2196   -3.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8023    1.1909   -2.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4267   -1.4273   -2.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8221    0.2017   -2.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8109    1.3725   -1.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6144   -0.1681   -1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5241   -2.0402    0.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2365   -1.5287   -1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2230    2.3673   -0.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5099    1.9717    1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1147    2.9612    1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -2.5050   -1.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0114   -2.9764   -0.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5579   -3.4017    0.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6081   -1.3243    2.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5655   -2.7567    2.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9422   -1.2092    2.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0432    0.3337    1.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8007   -0.9160    1.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5930   -2.0675    0.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8452    2.9640   -0.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8288    3.5395   -0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2132    3.0143   -1.7677 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
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  1  6
 17 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 23 24  2  0
 23 25  1  0
 25 26  1  0
 22  2  1  0
 22  5  1  0
 20  7  1  0
  7 25  1  1
  9 15  1  1
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  1
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  6 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
 10 39  1  0
 10 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  1
 21 51  1  0
 21 52  1  0
 26 53  1  0
 26 54  1  0
 26 55  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       4.452   0.324   1.403  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.824  -0.458   0.275  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.379   0.002  -1.078  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.154   0.139  -1.982  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.188  -0.651  -1.294  0.00  0.00           N+0
HETATM    6  C   UNK     0       0.839  -0.478  -1.694  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.013   0.231  -0.644  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.415   0.363  -0.966  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.130  -0.435   0.103  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.303  -1.194  -0.393  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.395  -0.180  -0.287  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.516  -0.296  -0.866  0.00  0.00           O+0
HETATM   13  N   UNK     0      -3.973   0.895   0.544  0.00  0.00           N+0
HETATM   14  C   UNK     0      -4.740   2.104   0.768  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.704   0.518   1.063  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.271   0.985   2.149  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.063  -1.333   0.741  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.001  -2.570  -0.070  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.572  -1.656   2.130  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.106  -0.453   0.717  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.451  -1.023   0.930  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.385  -0.194   0.092  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.037   1.255   0.096  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.790   2.160   0.498  0.00  0.00           O+0
HETATM   25  N   UNK     0       0.710   1.505  -0.425  0.00  0.00           N+0
HETATM   26  C   UNK     0       0.169   2.783  -0.682  0.00  0.00           C+0
HETATM   27  H   UNK     0       3.696   0.701   2.128  0.00  0.00           H+0
HETATM   28  H   UNK     0       5.107  -0.362   1.973  0.00  0.00           H+0
HETATM   29  H   UNK     0       5.099   1.139   1.016  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.002  -1.530   0.341  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.782   1.035  -0.934  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.114  -0.704  -1.477  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.372  -0.220  -3.006  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.802   1.191  -2.031  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.427  -1.427  -2.026  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.822   0.202  -2.589  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.811   1.373  -1.082  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.614  -0.168  -1.934  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.524  -2.040   0.296  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.236  -1.529  -1.447  0.00  0.00           H+0
HETATM   41  H   UNK     0      -5.223   2.367  -0.201  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.510   1.972   1.536  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.115   2.961   1.058  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.488  -2.505  -1.067  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.011  -2.976  -0.242  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.558  -3.402   0.457  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.608  -1.324   2.301  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.565  -2.757   2.275  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.942  -1.209   2.926  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.043   0.334   1.518  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.801  -0.916   1.999  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.593  -2.067   0.669  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.845   2.964  -0.250  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.829   3.539  -0.180  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.213   3.014  -1.768  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    1    3   22   30                                             
CONECT    3    2    4   31   32                                             
CONECT    4    3    5   33   34                                             
CONECT    5    4    6   22                                                  
CONECT    6    5    7   35   36                                             
CONECT    7    6    8   20   25                                             
CONECT    8    7    9   37   38                                             
CONECT    9    8   10   17   15                                             
CONECT   10    9   11   39   40                                             
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13   41   42   43                                             
CONECT   15   13   16    9                                                  
CONECT   16   15                                                            
CONECT   17    9   18   19   20                                             
CONECT   18   17   44   45   46                                             
CONECT   19   17   47   48   49                                             
CONECT   20   17   21    7   50                                             
CONECT   21   20   22   51   52                                             
CONECT   22   21   23    2    5                                             
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26    7                                                  
CONECT   26   25   53   54   55                                             
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    2                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
CONECT   33    4                                                            
CONECT   34    4                                                            
CONECT   35    6                                                            
CONECT   36    6                                                            
CONECT   37    8                                                            
CONECT   38    8                                                            
CONECT   39   10                                                            
CONECT   40   10                                                            
CONECT   41   14                                                            
CONECT   42   14                                                            
CONECT   43   14                                                            
CONECT   44   18                                                            
CONECT   45   18                                                            
CONECT   46   18                                                            
CONECT   47   19                                                            
CONECT   48   19                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   21                                                            
CONECT   52   21                                                            
CONECT   53   26                                                            
CONECT   54   26                                                            
CONECT   55   26                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  118    0
END

RDKit          3D

55 59  0  0  0  0  0  0  0  0999 V2000
    4.4519    0.3244    1.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8242   -0.4582    0.2752 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3789    0.0017   -1.0779 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1543    0.1391   -1.9821 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1877   -0.6505   -1.2942 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8388   -0.4782   -1.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0133    0.2307   -0.6442 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4152    0.3627   -0.9657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1302   -0.4347    0.1026 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3028   -1.1939   -0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3953   -0.1795   -0.2869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5162   -0.2957   -0.8655 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0012   -2.5703   -0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5720   -1.6560    2.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1056   -0.4528    0.7172 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4506   -1.0229    0.9300 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3853   -0.1939    0.0924 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0366    1.2554    0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7904    2.1599    0.4983 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7097    1.5051   -0.4246 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1694    2.7830   -0.6815 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6960    0.7011    2.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1075   -0.3623    1.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0994    1.1391    1.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0018   -1.5301    0.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7817    1.0352   -0.9336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1139   -0.7038   -1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3723   -0.2196   -3.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8023    1.1909   -2.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4267   -1.4273   -2.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8221    0.2017   -2.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8109    1.3725   -1.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6144   -0.1681   -1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5241   -2.0402    0.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2365   -1.5287   -1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2230    2.3673   -0.2007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5099    1.9717    1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1147    2.9612    1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -2.5050   -1.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0114   -2.9764   -0.2418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5579   -3.4017    0.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6081   -1.3243    2.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5655   -2.7567    2.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9422   -1.2092    2.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0432    0.3337    1.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8007   -0.9160    1.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5930   -2.0675    0.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8452    2.9640   -0.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8288    3.5395   -0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2132    3.0143   -1.7677 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
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  1  6
 17 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 23 24  2  0
 23 25  1  0
 25 26  1  0
 22  2  1  0
 22  5  1  0
 20  7  1  0
  7 25  1  1
  9 15  1  1
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  1
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  6 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
 10 39  1  0
 10 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  1
 21 51  1  0
 21 52  1  0
 26 53  1  0
 26 54  1  0
 26 55  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Aspergillimide	ChEBI

Chemical Formula

C₂₀H₂₉N₃O₃

Average Mass

359.4700 Da

Monoisotopic Mass

359.22089 Da

IUPAC Name

(1'S,3R,3'R,7'R,12'R)-1,4',4',12',14'-pentamethyl-9',14'-diazaspiro[pyrrolidine-3,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecane]-2,5,13'-trione

Traditional Name

(1'S,3R,3'R,7'R,12'R)-1,4',4',12',14'-pentamethyl-9',14'-diazaspiro[pyrrolidine-3,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecane]-2,5,13'-trione

CAS Registry Number

Not Available

SMILES

C[C@@H]1CCN2C[C@@]34C[C@@]5(CC(=O)N(C)C5=O)C(C)(C)[C@H]3C[C@@]12C(=O)N4C

InChI Identifier

InChI=1S/C20H29N3O3/c1-12-6-7-23-11-19-10-18(9-14(24)21(4)15(18)25)17(2,3)13(19)8-20(12,23)16(26)22(19)5/h12-13H,6-11H2,1-5H3/t12-,13-,18-,19+,20+/m1/s1

InChI Key

RTNMRJRMTGSUAE-DWPFRNKMSA-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	NPAtlas	9402989

Species Where Detected

Species Name	Source	Reference
Aspergillus japonicus JV-23	KNApSAcK Database	22123792
Aspergillus sp. IMI 337664	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaspirodecane derivatives

Sub Class

Not Available

Direct Parent

Azaspirodecane derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Azaspirodecane
Indolizidine
Delta-lactam
N-alkylpiperazine
N-methylpiperazine
Piperidinone
1,4-diazinane
Carboxylic acid imide, n-substituted
N-alkylpyrrolidine
Piperazine
Piperidine
2-pyrrolidone
Pyrrolidone
Carboxylic acid imide
Dicarboximide
Tertiary carboxylic acid amide
Pyrrolidine
Amino acid or derivatives
Tertiary amine
Lactam
Tertiary aliphatic amine
Carboxamide group
Azacycle
Carboxylic acid derivative
Organooxygen compound
Organopnictogen compound
Organic oxide
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Amine
Organonitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

dicarboximide (CHEBI:68203 )
alkaloid (CHEBI:68203 )
azaspiro compound (CHEBI:68203 )

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	1.4	ALOGPS
logP	0.48	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	19.65	ChemAxon
pKa (Strongest Basic)	8.83	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	60.93 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	96.16 m³·mol⁻¹	ChemAxon
Polarizability	38.91 Å³	ChemAxon
Number of Rings	5	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

NPA005397

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00016379

Chemspider ID

30785566

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70698047

PDB ID

Not Available

ChEBI ID

68203

Good Scents ID

Not Available

References

General References

Banks RM, Blanchflower SE, Everett JR, Manger BR, Reading C: Novel anthelmintic metabolites from an Aspergillus species; the aspergillimides. J Antibiot (Tokyo). 1997 Oct;50(10):840-6. doi: 10.7164/antibiotics.50.840. [PubMed:9402989 ]

Showing NP-Card for Aspergillimide (NP0023578)

MOL for NP0023578 (Aspergillimide)

3D MOL for NP0023578 (Aspergillimide)

3D SDF for NP0023578 (Aspergillimide)

3D-SDF for NP0023578 (Aspergillimide)

PDB for NP0023578 (Aspergillimide)

3D PDB for NP0023578 (Aspergillimide)

SMILES for NP0023578 (Aspergillimide)

INCHI for NP0023578 (Aspergillimide)

Structure for NP0023578 (Aspergillimide)

3D Structure for NP0023578 (Aspergillimide)