NP-MRD: Showing NP-Card for PF1018 (NP0022643)

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Record Information

Version

2.0

Created at

2021-01-06 07:50:17 UTC

Updated at

2021-07-15 17:39:36 UTC

NP-MRD ID

NP0022643

Secondary Accession Numbers

None

Natural Product Identification

Common Name

PF1018

Provided By

NPAtlas

Description

(2Z,7aS)-2-{3-[(1R,4S,5S,6Z,8R,11R,12R)-2,4,5,6,8,10-hexamethyltricyclo[6.3.1.0⁴,¹¹]Dodeca-2,6,9-trien-12-yl]-1-hydroxyprop-2-en-1-ylidene}-hexahydro-1H-pyrrolizine-1,3-dione belongs to the class of organic compounds known as pyrrolizidinones. Pyrrolizidinones are compounds containing a pyrrolizidine moiety which bears a ketone. Pyrrolizidine is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom. PF1018 is found in Humicola sp. PF1018 was first documented in 1994 (PMID: 8040055). Based on a literature review very few articles have been published on (2Z,7aS)-2-{3-[(1R,4S,5S,6Z,8R,11R,12R)-2,4,5,6,8,10-hexamethyltricyclo[6.3.1.0⁴,¹¹]Dodeca-2,6,9-trien-12-yl]-1-hydroxyprop-2-en-1-ylidene}-hexahydro-1H-pyrrolizine-1,3-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105363D          

 67 71  0  0  0  0            999 V2000
   -4.9379    0.4614   -2.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5589    0.2726   -1.8126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6017    1.0897   -2.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4593    1.3250   -1.3005 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3965    2.1301   -2.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0026    2.1583   -0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9056    1.7818    0.7443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0717    2.9267    1.7230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7830    0.6922    1.1381 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5962    0.5255    2.6594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6533   -0.6267    0.5401 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0405   -1.3011    0.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7342   -1.5809    1.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6796   -1.8805    0.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5657   -2.8204    0.8973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7712   -1.1243   -0.7816 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.7960   -0.5114   -2.7668 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9745   -0.4137   -0.7517 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4825    0.2950    1.4994 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5307   -0.9743    0.9108 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3574   -0.3129    1.9780 C   0  0  2  0  0  0  0  0  0  0  0  0
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    6.2708   -0.5933   -0.3001 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3118   -0.6100   -1.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9520    0.9068   -3.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8583    1.0464    1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9778   -0.4310    3.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1013    1.3291    3.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4196   -1.2397    1.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7222   -0.7377    0.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9622   -2.3372    0.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8927   -2.0052    2.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9560   -3.6673    1.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8516    0.3002   -3.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4470   -2.0530    1.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1679   -0.7159    2.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2056    0.7859    1.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2640   -1.0544   -0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9852    0.6766   -0.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
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 17  2  1  0  0  0  0
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 18  4  1  0  0  0  0
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  1 33  1  0  0  0  0
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  3 36  1  0  0  0  0
  5 37  1  0  0  0  0
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 13 51  1  0  0  0  0
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 16 55  1  6  0  0  0
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 28 64  1  0  0  0  0
 28 65  1  0  0  0  0
 29 66  1  0  0  0  0
 29 67  1  0  0  0  0
M  END

     RDKit          3D

 67 71  0  0  0  0  0  0  0  0999 V2000
   -4.9379    0.4614   -2.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5589    0.2726   -1.8126 C   0  0  0  0  0  0  0  0  0  0  0  0
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 29 67  1  0
M  END


  Mrv1652306242105363D          

 67 71  0  0  0  0            999 V2000
   -4.9379    0.4614   -2.3477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5589    0.2726   -1.8126 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4825    0.2950    1.4994 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4470   -2.0530    1.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1679   -0.7159    2.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2056    0.7859    1.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9258   -1.7050    1.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
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  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
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 18  4  1  0  0  0  0
 30 26  1  0  0  0  0
 17 11  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
  3 36  1  0  0  0  0
  5 37  1  0  0  0  0
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 29 66  1  0  0  0  0
 29 67  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0022643

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O\C(\C(\[H])=C(/[H])[C@]1([H])[C@@]2([H])C(=C([H])[C@]3(C([H])([H])[H])[C@@]2([H])C(=C([H])[C@]1(\C([H])=C(C([H])([H])[H])/[C@]3([H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])=C1/C(=O)N2C([H])([H])C([H])([H])C([H])([H])[C@@]2([H])C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H35NO3/c1-15-12-27(5)13-17(3)24-22(16(2)14-28(24,6)18(15)4)19(27)9-10-21(30)23-25(31)20-8-7-11-29(20)26(23)32/h9-10,12-14,18-20,22,24,30H,7-8,11H2,1-6H3/b10-9+,15-12-,23-21-/t18-,19+,20-,22+,24-,27+,28-/m0/s1

> <INCHI_KEY>
WDPIULZTNJKEMP-NROJMVRNSA-N

> <FORMULA>
C28H35NO3

> <MOLECULAR_WEIGHT>
433.592

> <EXACT_MASS>
433.261693991

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
50.215592471956356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z,7aS)-2-[(2E)-3-[(1R,4S,5S,6Z,8R,11R,12R)-2,4,5,6,8,10-hexamethyltricyclo[6.3.1.0^{4,11}]dodeca-2,6,9-trien-12-yl]-1-hydroxyprop-2-en-1-ylidene]-hexahydro-1H-pyrrolizine-1,3-dione

> <ALOGPS_LOGP>
4.71

> <JCHEM_LOGP>
3.8950739123333347

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.3988867054627

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.849518137477587

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0582931195774927

> <JCHEM_POLAR_SURFACE_AREA>
57.61

> <JCHEM_REFRACTIVITY>
131.78099999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,7aS)-2-[(2E)-3-[(1R,4S,5S,6Z,8R,11R,12R)-2,4,5,6,8,10-hexamethyltricyclo[6.3.1.0^{4,11}]dodeca-2,6,9-trien-12-yl]-1-hydroxyprop-2-en-1-ylidene]-tetrahydropyrrolizine-1,3-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 67 71  0  0  0  0  0  0  0  0999 V2000
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  2  3  2  0
  3  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  2  0
 14 15  1  0
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 16 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 17  2  1  0
 31 23  1  0
 18  4  1  0
 30 26  1  0
 17 11  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  5 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  1
 10 45  1  0
 10 46  1  0
 10 47  1  0
 12 48  1  0
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 15 52  1  0
 15 53  1  0
 15 54  1  0
 16 55  1  6
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 20 59  1  0
 22 60  1  0
 26 61  1  1
 27 62  1  0
 27 63  1  0
 28 64  1  0
 28 65  1  0
 29 66  1  0
 29 67  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      -4.938   0.461  -2.348  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.559   0.273  -1.813  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.602   1.090  -2.215  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.459   1.325  -1.301  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.397   2.130  -2.029  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.003   2.158  -0.161  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.906   1.782   0.744  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.072   2.927   1.723  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.783   0.692   1.138  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.596   0.526   2.659  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.653  -0.627   0.540  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.040  -1.301   0.661  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.734  -1.581   1.221  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.680  -1.881   0.489  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.566  -2.820   0.897  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.771  -1.124  -0.782  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.228  -0.783  -0.870  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.880   0.068  -0.702  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.446  -0.127  -1.317  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.580  -0.170  -0.658  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.816  -0.368  -1.387  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.796  -0.511  -2.767  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.974  -0.414  -0.752  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.236  -0.287   0.681  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.482   0.295   1.499  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.531  -0.974   0.911  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.357  -0.313   1.978  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.773  -0.602   1.487  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.655  -0.350   0.017  0.00  0.00           C+0
HETATM   30  N   UNK     0       6.271  -0.593  -0.300  0.00  0.00           N+0
HETATM   31  C   UNK     0       5.312  -0.610  -1.353  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.540  -0.763  -2.581  0.00  0.00           O+0
HETATM   33  H   UNK     0      -4.952   0.907  -3.354  0.00  0.00           H+0
HETATM   34  H   UNK     0      -5.403  -0.561  -2.453  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.548   1.035  -1.609  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.618   1.593  -3.181  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.565   1.988  -1.518  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.703   3.187  -1.967  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.389   1.825  -3.087  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.615   3.147  -0.087  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.713   3.879   1.305  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.149   3.073   1.959  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.545   2.741   2.660  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.858   1.046   1.063  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.978  -0.431   3.013  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.484   0.513   2.832  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.101   1.329   3.211  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.420  -1.240   1.678  0.00  0.00           H+0
HETATM   49  H   UNK     0      -5.722  -0.738   0.001  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.962  -2.337   0.269  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.893  -2.005   2.224  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.249  -2.268   1.400  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.956  -3.667   1.486  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.166  -3.225  -0.055  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.548  -1.771  -1.664  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.721  -1.728  -1.280  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.672   0.251   0.387  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.491  -0.244  -2.390  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.537  -0.058   0.390  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.852   0.300  -3.361  0.00  0.00           H+0
HETATM   61  H   UNK     0       5.447  -2.053   1.030  0.00  0.00           H+0
HETATM   62  H   UNK     0       6.168  -0.716   2.979  0.00  0.00           H+0
HETATM   63  H   UNK     0       6.206   0.786   1.938  0.00  0.00           H+0
HETATM   64  H   UNK     0       7.926  -1.705   1.638  0.00  0.00           H+0
HETATM   65  H   UNK     0       8.524  -0.001   2.002  0.00  0.00           H+0
HETATM   66  H   UNK     0       8.264  -1.054  -0.592  0.00  0.00           H+0
HETATM   67  H   UNK     0       7.985   0.677  -0.184  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    1    3   17                                                  
CONECT    3    2    4   36                                                  
CONECT    4    3    5    6   18                                             
CONECT    5    4   37   38   39                                             
CONECT    6    4    7   40                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7   41   42   43                                             
CONECT    9    7   10   11   44                                             
CONECT   10    9   45   46   47                                             
CONECT   11    9   12   13   17                                             
CONECT   12   11   48   49   50                                             
CONECT   13   11   14   51                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   52   53   54                                             
CONECT   16   14   17   18   55                                             
CONECT   17   16    2   11   56                                             
CONECT   18   16   19    4   57                                             
CONECT   19   18   20   58                                                  
CONECT   20   19   21   59                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   60                                                       
CONECT   23   21   24   31                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   30   61                                             
CONECT   27   26   28   62   63                                             
CONECT   28   27   29   64   65                                             
CONECT   29   28   30   66   67                                             
CONECT   30   29   31   26                                                  
CONECT   31   30   32   23                                                  
CONECT   32   31                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    3                                                            
CONECT   37    5                                                            
CONECT   38    5                                                            
CONECT   39    5                                                            
CONECT   40    6                                                            
CONECT   41    8                                                            
CONECT   42    8                                                            
CONECT   43    8                                                            
CONECT   44    9                                                            
CONECT   45   10                                                            
CONECT   46   10                                                            
CONECT   47   10                                                            
CONECT   48   12                                                            
CONECT   49   12                                                            
CONECT   50   12                                                            
CONECT   51   13                                                            
CONECT   52   15                                                            
CONECT   53   15                                                            
CONECT   54   15                                                            
CONECT   55   16                                                            
CONECT   56   17                                                            
CONECT   57   18                                                            
CONECT   58   19                                                            
CONECT   59   20                                                            
CONECT   60   22                                                            
CONECT   61   26                                                            
CONECT   62   27                                                            
CONECT   63   27                                                            
CONECT   64   28                                                            
CONECT   65   28                                                            
CONECT   66   29                                                            
CONECT   67   29                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  142    0
END

RDKit          3D

67 71  0  0  0  0  0  0  0  0999 V2000
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   -3.6533   -0.6267    0.5401 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0405   -1.3011    0.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7342   -1.5809    1.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6796   -1.8805    0.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5657   -2.8204    0.8973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7712   -1.1243   -0.7816 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2285   -0.7833   -0.8702 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8802    0.0679   -0.7015 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.4825    0.2950    1.4994 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8516    0.3002   -3.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4470   -2.0530    1.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1679   -0.7159    2.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2056    0.7859    1.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9258   -1.7050    1.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5245   -0.0007    2.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2640   -1.0544   -0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9852    0.6766   -0.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  2  0
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 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 17  2  1  0
 31 23  1  0
 18  4  1  0
 30 26  1  0
 17 11  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  5 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  1
 10 45  1  0
 10 46  1  0
 10 47  1  0
 12 48  1  0
 12 49  1  0
 12 50  1  0
 13 51  1  0
 15 52  1  0
 15 53  1  0
 15 54  1  0
 16 55  1  6
 17 56  1  6
 18 57  1  1
 19 58  1  0
 20 59  1  0
 22 60  1  0
 26 61  1  1
 27 62  1  0
 27 63  1  0
 28 64  1  0
 28 65  1  0
 29 66  1  0
 29 67  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₈H₃₅NO₃

Average Mass

433.5920 Da

Monoisotopic Mass

433.26169 Da

IUPAC Name

(2Z,7aS)-2-[(2E)-3-[(1R,4S,5S,6Z,8R,11R,12R)-2,4,5,6,8,10-hexamethyltricyclo[6.3.1.0^{4,11}]dodeca-2,6,9-trien-12-yl]-1-hydroxyprop-2-en-1-ylidene]-hexahydro-1H-pyrrolizine-1,3-dione

Traditional Name

(2Z,7aS)-2-[(2E)-3-[(1R,4S,5S,6Z,8R,11R,12R)-2,4,5,6,8,10-hexamethyltricyclo[6.3.1.0^{4,11}]dodeca-2,6,9-trien-12-yl]-1-hydroxyprop-2-en-1-ylidene]-tetrahydropyrrolizine-1,3-dione

CAS Registry Number

Not Available

SMILES

C[C@H]1\C(C)=C/[C@@]2(C)C=C(C)[C@H]3[C@@H]([C@H]2\C=C\C(\O)=C2/C(=O)[C@@H]4CCCN4C2=O)C(C)=C[C@@]13C

InChI Identifier

InChI=1S/C28H35NO3/c1-15-12-27(5)13-17(3)24-22(16(2)14-28(24,6)18(15)4)19(27)9-10-21(30)23-25(31)20-8-7-11-29(20)26(23)32/h9-10,12-14,18-20,22,24,30H,7-8,11H2,1-6H3/b10-9+,15-12-,23-21-/t18-,19+,20-,22+,24-,27+,28-/m0/s1

InChI Key

WDPIULZTNJKEMP-NROJMVRNSA-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
Humicola sp.	NPAtlas	8040055

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolizidinones. Pyrrolizidinones are compounds containing a pyrrolizidine moiety which bears a ketone. Pyrrolizidine is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolizidines

Sub Class

Pyrrolizidinones

Direct Parent

Pyrrolizidinones

Alternative Parents

Substituents

Pyrrolizidinone
Pyrrolidone
2-pyrrolidone
3-pyrrolidone
N-alkylpyrrolidine
Pyrrolidine
Tertiary carboxylic acid amide
Vinylogous acid
Lactam
Ketone
Carboxamide group
Enol
Carboxylic acid derivative
Azacycle
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

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	4.71	ALOGPS
logP	3.9	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	5.85	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.61 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	131.78 m³·mol⁻¹	ChemAxon
Polarizability	50.22 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA011187

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58826221

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54710416

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gomi S, Imamura K, Yaguchi T, Kodama Y, Minowa N, Koyama M: PF1018, a novel insecticidal compound produced by Humicola sp. J Antibiot (Tokyo). 1994 May;47(5):571-80. doi: 10.7164/antibiotics.47.571. [PubMed:8040055 ]

Showing NP-Card for PF1018 (NP0022643)

MOL for NP0022643 (PF1018)

3D MOL for NP0022643 (PF1018)

3D SDF for NP0022643 (PF1018)

3D-SDF for NP0022643 (PF1018)

PDB for NP0022643 (PF1018)

3D PDB for NP0022643 (PF1018)

SMILES for NP0022643 (PF1018)

INCHI for NP0022643 (PF1018)

Structure for NP0022643 (PF1018)

3D Structure for NP0022643 (PF1018)