NP-MRD: Showing NP-Card for Reutericyclin (NP0003371)

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Record Information

Version

1.0

Created at

2020-12-09 00:39:06 UTC

Updated at

2021-07-15 16:46:15 UTC

NP-MRD ID

NP0003371

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Reutericyclin

Provided By

NPAtlas

Description

(5R)-3-acetyl-1-[(2E)-dec-2-enoyl]-4-hydroxy-5-(2-methylpropyl)-2,5-dihydro-1H-pyrrol-2-one belongs to the class of organic compounds known as n-substituted carboxylic acid imides. N-substituted carboxylic acid imides are compounds comprising an N-substituted carboxylic acid imide group, with the general structure R1N(C(R2)=O)C(R3)=O (R2,R3=H, alkyl, aryl; R1=Anything but H). Reutericyclin is found in Unknown-fungus sp. It was first documented in 2000 (PMID: 10934421). Based on a literature review very few articles have been published on (5R)-3-acetyl-1-[(2E)-dec-2-enoyl]-4-hydroxy-5-(2-methylpropyl)-2,5-dihydro-1H-pyrrol-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117473D          

 56 56  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242117473D          

 56 56  0  0  0  0            999 V2000
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    4.6472   -2.5362    2.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5339   -2.2463    0.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8856   -0.9169    1.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2440   -0.6227   -1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3091    0.6163    0.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0920    0.5879   -0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0165   -1.2339    1.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3951    3.6524   -1.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8183    4.4910   -2.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3748    2.7467   -2.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9808    1.3507   -1.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3166    0.5171    1.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6200   -1.3093   -0.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1303   -1.8629    0.7197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9411   -0.8280   -0.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4582   -1.2004    2.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7851   -1.7058    2.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1458    0.0065    2.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0916   -3.2345   -0.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1271   -3.3418    1.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6210   -2.9328    0.3728 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  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 15 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 21 12  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  2 29  1  0  0  0  0
  2 30  1  0  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
  5 35  1  0  0  0  0
  5 36  1  0  0  0  0
  6 37  1  0  0  0  0
  6 38  1  0  0  0  0
  7 39  1  0  0  0  0
  7 40  1  0  0  0  0
  8 41  1  0  0  0  0
  9 42  1  0  0  0  0
 17 43  1  0  0  0  0
 17 44  1  0  0  0  0
 17 45  1  0  0  0  0
 20 46  1  0  0  0  0
 21 47  1  1  0  0  0
 22 48  1  0  0  0  0
 22 49  1  0  0  0  0
 23 50  1  6  0  0  0
 24 51  1  0  0  0  0
 24 52  1  0  0  0  0
 24 53  1  0  0  0  0
 25 54  1  0  0  0  0
 25 55  1  0  0  0  0
 25 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003371

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C(=O)C([H])([H])[H])C(=O)N(C(=O)C(\[H])=C(/[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])[C@]1([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H31NO4/c1-5-6-7-8-9-10-11-12-17(23)21-16(13-14(2)3)19(24)18(15(4)22)20(21)25/h11-12,14,16,24H,5-10,13H2,1-4H3/b12-11+/t16-/m1/s1

> <INCHI_KEY>
GNGSBVNLHSNSDF-LPQFERQCSA-N

> <FORMULA>
C20H31NO4

> <MOLECULAR_WEIGHT>
349.471

> <EXACT_MASS>
349.225308482

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
40.72170275139891

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R)-3-acetyl-1-[(2E)-dec-2-enoyl]-4-hydroxy-5-(2-methylpropyl)-2,5-dihydro-1H-pyrrol-2-one

> <ALOGPS_LOGP>
4.03

> <JCHEM_LOGP>
4.289776841666667

> <ALOGPS_LOGS>
-4.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.026277043874153

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.680785740633005

> <JCHEM_PKA_STRONGEST_BASIC>
-3.369735788348271

> <JCHEM_POLAR_SURFACE_AREA>
74.68

> <JCHEM_REFRACTIVITY>
100.30039999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R)-3-acetyl-1-[(2E)-dec-2-enoyl]-4-hydroxy-5-(2-methylpropyl)-5H-pyrrol-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 56  0  0  0  0  0  0  0  0999 V2000
    7.4727    1.6029   -0.9609 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2239    0.8188    0.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0328   -0.1273   -0.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5639    3.4833   -2.6925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9836    1.2457   -0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3644    1.5336   -0.2712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2845    0.2601    0.4863 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7840   -1.1500    0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2178   -1.3329    0.5661 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4046   -1.0381    2.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5167   -2.8327    0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6517    2.3677   -1.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4380    0.9170   -1.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4532    2.0975   -0.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9769    1.4682    1.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0687    0.1220    0.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2601    0.4464   -0.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4076   -0.8408   -0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6462   -1.4898    1.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4472   -0.2070    2.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8278   -2.6286    0.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6472   -2.5362    2.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5339   -2.2463    0.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8856   -0.9169    1.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2440   -0.6227   -1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3091    0.6163    0.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0920    0.5879   -0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0165   -1.2339    1.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3951    3.6524   -1.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8183    4.4910   -2.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3748    2.7467   -2.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9808    1.3507   -1.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3166    0.5171    1.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6200   -1.3093   -0.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1303   -1.8629    0.7197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9411   -0.8280   -0.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4582   -1.2004    2.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7851   -1.7058    2.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1458    0.0065    2.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0916   -3.2345   -0.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1271   -3.3418    1.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6210   -2.9328    0.3728 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  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 15 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 21 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  9 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 20 46  1  0
 21 47  1  1
 22 48  1  0
 22 49  1  0
 23 50  1  6
 24 51  1  0
 24 52  1  0
 24 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  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       7.473   1.603  -0.961  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.224   0.819   0.311  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.033  -0.127  -0.002  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.724  -0.932   1.192  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.613  -1.881   1.050  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.251  -1.349   0.922  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.909  -0.417  -0.147  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.417  -0.073  -0.192  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.541  -0.539   0.629  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.859  -0.374   0.789  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.378  -1.092   1.788  0.00  0.00           O+0
HETATM   12  N   UNK     0      -1.852   0.385   0.125  0.00  0.00           N+0
HETATM   13  C   UNK     0      -1.799   1.390  -0.855  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.788   1.830  -1.482  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.168   1.899  -1.067  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.472   2.964  -2.016  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.849   3.476  -2.226  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.564   3.483  -2.692  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.984   1.246  -0.284  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.364   1.534  -0.271  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.285   0.260   0.486  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.784  -1.150   0.219  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.218  -1.333   0.566  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.405  -1.038   2.042  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.517  -2.833   0.416  0.00  0.00           C+0
HETATM   26  H   UNK     0       6.652   2.368  -1.018  0.00  0.00           H+0
HETATM   27  H   UNK     0       7.438   0.917  -1.834  0.00  0.00           H+0
HETATM   28  H   UNK     0       8.453   2.098  -0.847  0.00  0.00           H+0
HETATM   29  H   UNK     0       6.977   1.468   1.151  0.00  0.00           H+0
HETATM   30  H   UNK     0       8.069   0.122   0.530  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.260   0.446  -0.433  0.00  0.00           H+0
HETATM   32  H   UNK     0       6.408  -0.841  -0.798  0.00  0.00           H+0
HETATM   33  H   UNK     0       6.646  -1.490   1.574  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.447  -0.207   2.023  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.828  -2.629   0.193  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.647  -2.536   2.002  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.534  -2.246   0.809  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.886  -0.917   1.912  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.244  -0.623  -1.155  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.309   0.616   0.212  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.092   0.588  -0.969  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.016  -1.234   1.397  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.395   3.652  -1.277  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.818   4.491  -2.713  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.375   2.747  -2.875  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.981   1.351  -1.028  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.317   0.517   1.568  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.620  -1.309  -0.888  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.130  -1.863   0.720  0.00  0.00           H+0
HETATM   50  H   UNK     0      -5.941  -0.828  -0.064  0.00  0.00           H+0
HETATM   51  H   UNK     0      -6.458  -1.200   2.370  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.785  -1.706   2.674  0.00  0.00           H+0
HETATM   53  H   UNK     0      -5.146   0.007   2.308  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.092  -3.235  -0.505  0.00  0.00           H+0
HETATM   55  H   UNK     0      -5.127  -3.342   1.342  0.00  0.00           H+0
HETATM   56  H   UNK     0      -6.621  -2.933   0.373  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    1    3   29   30                                             
CONECT    3    2    4   31   32                                             
CONECT    4    3    5   33   34                                             
CONECT    5    4    6   35   36                                             
CONECT    6    5    7   37   38                                             
CONECT    7    6    8   39   40                                             
CONECT    8    7    9   41                                                  
CONECT    9    8   10   42                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   21                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   43   44   45                                             
CONECT   18   16                                                            
CONECT   19   15   20   21                                                  
CONECT   20   19   46                                                       
CONECT   21   19   22   12   47                                             
CONECT   22   21   23   48   49                                             
CONECT   23   22   24   25   50                                             
CONECT   24   23   51   52   53                                             
CONECT   25   23   54   55   56                                             
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    2                                                            
CONECT   30    2                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
CONECT   33    4                                                            
CONECT   34    4                                                            
CONECT   35    5                                                            
CONECT   36    5                                                            
CONECT   37    6                                                            
CONECT   38    6                                                            
CONECT   39    7                                                            
CONECT   40    7                                                            
CONECT   41    8                                                            
CONECT   42    9                                                            
CONECT   43   17                                                            
CONECT   44   17                                                            
CONECT   45   17                                                            
CONECT   46   20                                                            
CONECT   47   21                                                            
CONECT   48   22                                                            
CONECT   49   22                                                            
CONECT   50   23                                                            
CONECT   51   24                                                            
CONECT   52   24                                                            
CONECT   53   24                                                            
CONECT   54   25                                                            
CONECT   55   25                                                            
CONECT   56   25                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  112    0
END

RDKit          3D

56 56  0  0  0  0  0  0  0  0999 V2000
    7.4727    1.6029   -0.9609 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2239    0.8188    0.3105 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0328   -0.1273   -0.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7237   -0.9322    1.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6131   -1.8807    1.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2508   -1.3489    0.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9093   -0.4167   -0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4174   -0.0731   -0.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5405   -0.5388    0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8591   -0.3744    0.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3776   -1.0919    1.7881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8516    0.3847    0.1248 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7989    1.3902   -0.8545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7882    1.8303   -1.4821 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1677    1.8992   -1.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4724    2.9636   -2.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8490    3.4757   -2.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5639    3.4833   -2.6925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9836    1.2457   -0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3644    1.5336   -0.2712 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2845    0.2601    0.4863 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7840   -1.1500    0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2178   -1.3329    0.5661 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4046   -1.0381    2.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5167   -2.8327    0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6517    2.3677   -1.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4380    0.9170   -1.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4532    2.0975   -0.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9769    1.4682    1.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0687    0.1220    0.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2601    0.4464   -0.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4076   -0.8408   -0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6462   -1.4898    1.5738 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4472   -0.2070    2.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8278   -2.6286    0.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6472   -2.5362    2.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5339   -2.2463    0.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8856   -0.9169    1.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2440   -0.6227   -1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3091    0.6163    0.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0920    0.5879   -0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0165   -1.2339    1.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3951    3.6524   -1.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8183    4.4910   -2.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3748    2.7467   -2.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9808    1.3507   -1.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3166    0.5171    1.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6200   -1.3093   -0.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1303   -1.8629    0.7197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9411   -0.8280   -0.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4582   -1.2004    2.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7851   -1.7058    2.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1458    0.0065    2.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0916   -3.2345   -0.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1271   -3.3418    1.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6210   -2.9328    0.3728 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  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 15 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 21 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  9 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 20 46  1  0
 21 47  1  1
 22 48  1  0
 22 49  1  0
 23 50  1  6
 24 51  1  0
 24 52  1  0
 24 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₀H₃₁NO₄

Average Mass

349.4710 Da

Monoisotopic Mass

349.22531 Da

IUPAC Name

(5R)-3-acetyl-1-[(2E)-dec-2-enoyl]-4-hydroxy-5-(2-methylpropyl)-2,5-dihydro-1H-pyrrol-2-one

Traditional Name

(5R)-3-acetyl-1-[(2E)-dec-2-enoyl]-4-hydroxy-5-(2-methylpropyl)-5H-pyrrol-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCC\C=C\C(=O)N1[C@H](CC(C)C)C(O)=C(C(C)=O)C1=O

InChI Identifier

InChI=1S/C20H31NO4/c1-5-6-7-8-9-10-11-12-17(23)21-16(13-14(2)3)19(24)18(15(4)22)20(21)25/h11-12,14,16,24H,5-10,13H2,1-4H3/b12-11+/t16-/m1/s1

InChI Key

GNGSBVNLHSNSDF-LPQFERQCSA-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
Unknown-fungus sp.	NPAtlas	10934421

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-substituted carboxylic acid imides. N-substituted carboxylic acid imides are compounds comprising an N-substituted carboxylic acid imide group, with the general structure R1N(C(R2)=O)C(R3)=O (R2,R3=H, alkyl, aryl; R1=Anything but H).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

N-substituted carboxylic acid imides

Alternative Parents

Substituents

Carboxylic acid imide, n-substituted
Dicarboximide
Pyrroline
Vinylogous acid
Ketone
Azacycle
Organoheterocyclic compound
Enol
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	4.03	ALOGPS
logP	4.29	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	3.68	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.68 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	100.3 m³·mol⁻¹	ChemAxon
Polarizability	40.72 Å³	ChemAxon
Number of Rings	1	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

NPA018209

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78438453

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54684555

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Holtzel A, Ganzle MG, Nicholson GJ, Hammes WP, Jung G: The First Low Molecular Weight Antibiotic from Lactic Acid Bacteria: Reutericyclin, a New Tetramic Acid. Angew Chem Int Ed Engl. 2000 Aug 4;39(15):2766-2768. [PubMed:10934421 ]

Showing NP-Card for Reutericyclin (NP0003371)

MOL for NP0003371 (Reutericyclin)

3D MOL for NP0003371 (Reutericyclin)

3D SDF for NP0003371 (Reutericyclin)

3D-SDF for NP0003371 (Reutericyclin)

PDB for NP0003371 (Reutericyclin)

3D PDB for NP0003371 (Reutericyclin)

SMILES for NP0003371 (Reutericyclin)

INCHI for NP0003371 (Reutericyclin)

Structure for NP0003371 (Reutericyclin)

3D Structure for NP0003371 (Reutericyclin)