NP-MRD: Showing NP-Card for Coniosetin (NP0004584)

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Record Information

Version

2.0

Created at

2020-12-09 02:02:13 UTC

Updated at

2021-07-15 16:49:35 UTC

NP-MRD ID

NP0004584

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Coniosetin

Provided By

NPAtlas

Description

(4Z)-4-{[(1S,2R,4aS,6R,8aR)-1,3,6-trimethyl-2-[(1E,3E)-penta-1,3-dien-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl](hydroxy)methylidene}-5-hydroxy-2-(1-hydroxyethyl)-3,4-dihydro-2H-pyrrol-3-one belongs to the class of organic compounds known as pyrrolidine-3-ones. These are pyrrolidines which bear a C=O group at position 3 of the pyrrolidine ring. Coniosetin is found in Coniochaeta, Coniochaeta ellipsoidea and Coniochaeta ellipsoidea DSM 13856. Coniosetin was first documented in 2003 (PMID: 12715870). Based on a literature review very few articles have been published on (4Z)-4-{[(1S,2R,4aS,6R,8aR)-1,3,6-trimethyl-2-[(1E,3E)-penta-1,3-dien-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl](hydroxy)methylidene}-5-hydroxy-2-(1-hydroxyethyl)-3,4-dihydro-2H-pyrrol-3-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118073D          

 65 67  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242118073D          

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   -3.2933   -4.9285    0.8814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4045   -3.4622   -0.9454 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.8358   -0.3304   -0.6986 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4180   -0.7012   -2.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5776   -0.3840   -1.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0598   -0.7583   -2.3453 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6091   -0.0970   -0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4825    0.3181    1.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4476    0.4808    1.7447 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8047    0.5235    1.6661 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7706    0.5122    0.6074 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9946   -0.3122    0.9418 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9227   -0.3191   -0.2446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6241   -1.6439    1.1905 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0487   -0.1462   -0.5399 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5743   -0.6356   -1.5438 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4700   -1.3556   -0.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4153   -3.5551   -0.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1193   -4.9625    1.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3136   -4.9868    1.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1269   -4.4923   -1.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8193   -2.9570   -1.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4795   -0.5356   -2.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9853   -1.5911   -2.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9930    0.1391   -2.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6343   -1.5597   -2.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0207    0.6586    2.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0866    1.5279    0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5349    0.1078    1.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7440   -1.2181   -0.8984 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9901   -0.3954    0.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8529    0.5841   -0.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4455   -2.1857    1.2112 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  2  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
  7  9  2  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  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  6  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 25 29  1  0  0  0  0
 29 30  2  0  0  0  0
 17  6  1  0  0  0  0
 29 21  1  0  0  0  0
 16 10  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  2 34  1  0  0  0  0
  3 35  1  0  0  0  0
  4 36  1  0  0  0  0
  5 37  1  0  0  0  0
  6 38  1  6  0  0  0
  8 39  1  0  0  0  0
  8 40  1  0  0  0  0
  8 41  1  0  0  0  0
  9 42  1  0  0  0  0
 10 43  1  6  0  0  0
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 15 52  1  0  0  0  0
 15 53  1  0  0  0  0
 16 54  1  1  0  0  0
 18 55  1  0  0  0  0
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 20 58  1  0  0  0  0
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 27 62  1  0  0  0  0
 27 63  1  0  0  0  0
 27 64  1  0  0  0  0
 28 65  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004584

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O\C(=C1\C(=O)N([H])[C@]([H])(C1=O)[C@@]([H])(O[H])C([H])([H])[H])[C@]1(C([H])([H])[H])[C@]([H])(C(\[H])=C(/[H])\C(\[H])=C(/[H])C([H])([H])[H])C(=C([H])[C@]2([H])C([H])([H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]12[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H35NO4/c1-6-7-8-9-18-15(3)13-17-12-14(2)10-11-19(17)25(18,5)23(29)20-22(28)21(16(4)27)26-24(20)30/h6-9,13-14,16-19,21,27,29H,10-12H2,1-5H3,(H,26,30)/b7-6+,9-8+,23-20+/t14-,16+,17+,18-,19-,21+,25-/m1/s1

> <INCHI_KEY>
ISHIUSZGAFLPLK-MSLMHWDWSA-N

> <FORMULA>
C25H35NO4

> <MOLECULAR_WEIGHT>
413.558

> <EXACT_MASS>
413.256608611

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
47.222419186674486

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E,5S)-3-{[(1S,4aS,6R,8aR)-1,3,6-trimethyl-2-[(1E,3E)-penta-1,3-dien-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl](hydroxy)methylidene}-5-[(1S)-1-hydroxyethyl]pyrrolidine-2,4-dione

> <ALOGPS_LOGP>
4.13

> <JCHEM_LOGP>
3.6330695223333334

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.413443438469413

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.732353602391624

> <JCHEM_PKA_STRONGEST_BASIC>
-0.95011160902812

> <JCHEM_POLAR_SURFACE_AREA>
86.63

> <JCHEM_REFRACTIVITY>
122.35429999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E,5S)-3-{[(1S,4aS,6R,8aR)-1,3,6-trimethyl-2-[(1E,3E)-penta-1,3-dien-1-yl]-4a,5,6,7,8,8a-hexahydro-2H-naphthalen-1-yl](hydroxy)methylidene}-5-[(1S)-1-hydroxyethyl]pyrrolidine-2,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 65 67  0  0  0  0  0  0  0  0999 V2000
    1.8301    6.2388    0.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9716    5.0932    0.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5792    4.1583   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2933   -4.9285    0.8814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4045   -3.4622   -0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1135   -2.8185   -0.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4180   -0.7012   -2.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5776   -0.3840   -1.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4825    0.3181    1.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4476    0.4808    1.7447 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8047    0.5235    1.6661 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7706    0.5122    0.6074 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9946   -0.3122    0.9418 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9227   -0.3191   -0.2446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6241   -1.6439    1.1905 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0207    0.6586    2.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8529    0.5841   -0.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4455   -2.1857    1.2112 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  6
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 25 29  1  0
 29 30  2  0
 17  6  1  0
 29 21  1  0
 16 10  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  3 35  1  0
  4 36  1  0
  5 37  1  0
  6 38  1  6
  8 39  1  0
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 24 59  1  0
 25 60  1  6
 26 61  1  1
 27 62  1  0
 27 63  1  0
 27 64  1  0
 28 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       1.830   6.239   0.061  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.972   5.093   0.421  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.579   4.158  -0.417  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.280   3.050   0.037  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.648   2.143  -0.822  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.486   1.012  -0.522  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.462   1.120   0.578  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.844   2.364   1.305  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.133   0.022   0.968  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.884  -1.242   0.294  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.318  -2.446   1.155  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.406  -3.601   0.178  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.293  -4.928   0.881  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.405  -3.462  -0.945  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.113  -2.818  -0.425  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.388  -1.435   0.128  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.836  -0.330  -0.699  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.418  -0.701  -2.109  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.578  -0.384  -1.050  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.060  -0.758  -2.345  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.609  -0.097  -0.241  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.482   0.318   1.121  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.448   0.481   1.745  0.00  0.00           O+0
HETATM   24  N   UNK     0       2.805   0.524   1.666  0.00  0.00           N+0
HETATM   25  C   UNK     0       3.771   0.512   0.607  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.995  -0.312   0.942  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.923  -0.319  -0.245  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.624  -1.644   1.190  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.049  -0.146  -0.540  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.574  -0.636  -1.544  0.00  0.00           O+0
HETATM   31  H   UNK     0       1.449   7.129   0.621  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.891   6.064   0.335  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.719   6.510  -1.026  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.645   5.032   1.468  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.905   4.236  -1.424  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.537   3.042   1.092  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.265   2.289  -1.854  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.296   1.155  -1.377  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.967   2.306   1.538  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.406   2.444   2.317  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.788   3.280   0.689  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.853   0.066   1.774  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.470  -1.356  -0.631  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.531  -2.693   1.889  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.290  -2.197   1.590  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.415  -3.555  -0.282  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.119  -4.963   1.630  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.472  -5.726   0.158  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.314  -4.987   1.392  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.127  -4.492  -1.257  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.819  -2.957  -1.812  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.313  -2.887  -1.149  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.808  -3.540   0.397  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.054  -1.509   1.179  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.479  -0.536  -2.145  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.985  -1.591  -2.519  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.993   0.139  -2.751  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.634  -1.560  -2.473  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.021   0.659   2.671  0.00  0.00           H+0
HETATM   60  H   UNK     0       4.087   1.528   0.377  0.00  0.00           H+0
HETATM   61  H   UNK     0       5.535   0.108   1.805  0.00  0.00           H+0
HETATM   62  H   UNK     0       5.744  -1.218  -0.898  0.00  0.00           H+0
HETATM   63  H   UNK     0       6.990  -0.395   0.074  0.00  0.00           H+0
HETATM   64  H   UNK     0       5.853   0.584  -0.867  0.00  0.00           H+0
HETATM   65  H   UNK     0       5.446  -2.186   1.211  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    1    3   34                                                  
CONECT    3    2    4   35                                                  
CONECT    4    3    5   36                                                  
CONECT    5    4    6   37                                                  
CONECT    6    5    7   17   38                                             
CONECT    7    6    8    9                                                  
CONECT    8    7   39   40   41                                             
CONECT    9    7   10   42                                                  
CONECT   10    9   11   16   43                                             
CONECT   11   10   12   44   45                                             
CONECT   12   11   13   14   46                                             
CONECT   13   12   47   48   49                                             
CONECT   14   12   15   50   51                                             
CONECT   15   14   16   52   53                                             
CONECT   16   15   17   10   54                                             
CONECT   17   16   18   19    6                                             
CONECT   18   17   55   56   57                                             
CONECT   19   17   20   21                                                  
CONECT   20   19   58                                                       
CONECT   21   19   22   29                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   59                                                  
CONECT   25   24   26   29   60                                             
CONECT   26   25   27   28   61                                             
CONECT   27   26   62   63   64                                             
CONECT   28   26   65                                                       
CONECT   29   25   30   21                                                  
CONECT   30   29                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    2                                                            
CONECT   35    3                                                            
CONECT   36    4                                                            
CONECT   37    5                                                            
CONECT   38    6                                                            
CONECT   39    8                                                            
CONECT   40    8                                                            
CONECT   41    8                                                            
CONECT   42    9                                                            
CONECT   43   10                                                            
CONECT   44   11                                                            
CONECT   45   11                                                            
CONECT   46   12                                                            
CONECT   47   13                                                            
CONECT   48   13                                                            
CONECT   49   13                                                            
CONECT   50   14                                                            
CONECT   51   14                                                            
CONECT   52   15                                                            
CONECT   53   15                                                            
CONECT   54   16                                                            
CONECT   55   18                                                            
CONECT   56   18                                                            
CONECT   57   18                                                            
CONECT   58   20                                                            
CONECT   59   24                                                            
CONECT   60   25                                                            
CONECT   61   26                                                            
CONECT   62   27                                                            
CONECT   63   27                                                            
CONECT   64   27                                                            
CONECT   65   28                                                            
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
    1.8301    6.2388    0.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9716    5.0932    0.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5792    4.1583   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2804    3.0499    0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6484    2.1429   -0.8220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4860    1.0124   -0.5217 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4616    1.1203    0.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8438    2.3635    1.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1331    0.0217    0.9679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8841   -1.2417    0.2938 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3184   -2.4459    1.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4058   -3.6006    0.1779 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2933   -4.9285    0.8814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4045   -3.4622   -0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1135   -2.8185   -0.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3881   -1.4346    0.1277 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8358   -0.3304   -0.6986 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4180   -0.7012   -2.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5776   -0.3840   -1.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0598   -0.7583   -2.3453 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6091   -0.0970   -0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4825    0.3181    1.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4476    0.4808    1.7447 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8047    0.5235    1.6661 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7706    0.5122    0.6074 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9946   -0.3122    0.9418 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9227   -0.3191   -0.2446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6241   -1.6439    1.1905 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0487   -0.1462   -0.5399 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5743   -0.6356   -1.5438 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4494    7.1287    0.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8907    6.0638    0.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7186    6.5103   -1.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6451    5.0318    1.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9051    4.2357   -1.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5365    3.0423    1.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2647    2.2892   -1.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2957    1.1553   -1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9666    2.3057    1.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4056    2.4439    2.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7884    3.2803    0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8532    0.0661    1.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4700   -1.3556   -0.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5311   -2.6928    1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2899   -2.1966    1.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4153   -3.5551   -0.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1193   -4.9625    1.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4723   -5.7260    0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3136   -4.9868    1.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1269   -4.4923   -1.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8193   -2.9570   -1.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3127   -2.8870   -1.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8077   -3.5397    0.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0536   -1.5093    1.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4795   -0.5356   -2.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9853   -1.5911   -2.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9930    0.1391   -2.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6343   -1.5597   -2.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0207    0.6586    2.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0866    1.5279    0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5349    0.1078    1.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7440   -1.2181   -0.8984 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9901   -0.3954    0.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8529    0.5841   -0.8670 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4455   -2.1857    1.2112 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  6
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 25 29  1  0
 29 30  2  0
 17  6  1  0
 29 21  1  0
 16 10  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  3 35  1  0
  4 36  1  0
  5 37  1  0
  6 38  1  6
  8 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  6
 11 44  1  0
 11 45  1  0
 12 46  1  6
 13 47  1  0
 13 48  1  0
 13 49  1  0
 14 50  1  0
 14 51  1  0
 15 52  1  0
 15 53  1  0
 16 54  1  1
 18 55  1  0
 18 56  1  0
 18 57  1  0
 20 58  1  0
 24 59  1  0
 25 60  1  6
 26 61  1  1
 27 62  1  0
 27 63  1  0
 27 64  1  0
 28 65  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₅H₃₅NO₄

Average Mass

413.5580 Da

Monoisotopic Mass

413.25661 Da

IUPAC Name

(3E,5S)-3-{[(1S,4aS,6R,8aR)-1,3,6-trimethyl-2-[(1E,3E)-penta-1,3-dien-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl](hydroxy)methylidene}-5-[(1S)-1-hydroxyethyl]pyrrolidine-2,4-dione

Traditional Name

(3E,5S)-3-{[(1S,4aS,6R,8aR)-1,3,6-trimethyl-2-[(1E,3E)-penta-1,3-dien-1-yl]-4a,5,6,7,8,8a-hexahydro-2H-naphthalen-1-yl](hydroxy)methylidene}-5-[(1S)-1-hydroxyethyl]pyrrolidine-2,4-dione

CAS Registry Number

Not Available

SMILES

C\C=C\C=C\[C@@H]1C(C)=C[C@@H]2C[C@H](C)CC[C@H]2[C@]1(C)C(\O)=C1/C(=O)NC(C(C)O)C1=O

InChI Identifier

InChI=1S/C25H35NO4/c1-6-7-8-9-18-15(3)13-17-12-14(2)10-11-19(17)25(18,5)23(29)20-22(28)21(16(4)27)26-24(20)30/h6-9,13-14,16-19,21,27,29H,10-12H2,1-5H3,(H,26,30)/b7-6+,9-8+,23-20+/t14-,16?,17+,18-,19-,21?,25-/m1/s1

InChI Key

ISHIUSZGAFLPLK-MSLMHWDWSA-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
Coniochaeta	NPAtlas	12715870
Coniochaeta ellipsoidea	LOTUS Database	35616633
Coniochaeta ellipsoidea DSM 13856	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolidine-3-ones. These are pyrrolidines which bear a C=O group at position 3 of the pyrrolidine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolidines

Sub Class

Pyrrolidones

Direct Parent

Pyrrolidine-3-ones

Alternative Parents

Substituents

2-pyrrolidone
3-pyrrolidone
Vinylogous acid
Carboxamide group
Ketone
Lactam
Secondary alcohol
Cyclic ketone
Secondary carboxylic acid amide
Carboxylic acid derivative
Enol
Azacycle
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	4.13	ALOGPS
logP	3.63	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	4.73	ChemAxon
pKa (Strongest Basic)	-0.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	122.35 m³·mol⁻¹	ChemAxon
Polarizability	47.22 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	No	ChemAxon

External Links

NPAtlas ID

NPA001750

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78436449

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54724406

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Segeth MP, Bonnefoy A, Bronstrup M, Knauf M, Schummer D, Toti L, Vertesy L, Wetzel-Raynal MC, Wink J, Seibert G: Coniosetin, a novel tetramic acid antibiotic from Coniochaeta ellipsoidea DSM 13856. J Antibiot (Tokyo). 2003 Feb;56(2):114-22. doi: 10.7164/antibiotics.56.114. [PubMed:12715870 ]

Showing NP-Card for Coniosetin (NP0004584)

MOL for NP0004584 (Coniosetin)

3D MOL for NP0004584 (Coniosetin)

3D SDF for NP0004584 (Coniosetin)

3D-SDF for NP0004584 (Coniosetin)

PDB for NP0004584 (Coniosetin)

3D PDB for NP0004584 (Coniosetin)

SMILES for NP0004584 (Coniosetin)

INCHI for NP0004584 (Coniosetin)

Structure for NP0004584 (Coniosetin)

3D Structure for NP0004584 (Coniosetin)