NP-MRD: Showing NP-Card for Lolicine A (NP0001696)

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Record Information

Version

2.0

Created at

2020-09-25 15:38:45 UTC

Updated at

2021-07-15 16:45:04 UTC

NP-MRD ID

NP0001696

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lolicine A

Provided By

NPAtlas

Description

Lolicine A is found in Lolium perenne and Neotyphodium. Lolicine A was first documented in 1998 (PMID: 10554283). Based on a literature review very few articles have been published on (2S,3S,6S,8S,10R,11R,12R,15S,21R,25R)-10-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,11,22,22,24,24-heptamethyl-7,23-dioxa-31-azaoctacyclo[15.14.0.0²,¹⁵.0³,¹².0⁶,¹¹.0¹⁸,³⁰.0¹⁹,²⁷.0²¹,²⁵]Hentriaconta-1(17),18(30),19(27),28-tetraen-26-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652307012117053D          

 97104  0  0  0  0            999 V2000
    8.5820   -0.4715   -0.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0983    0.4704    0.4929 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7287    0.1439    1.8232 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9464   -0.6385    1.1925 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3212   -1.3818    0.0015 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.2196   -0.5980   -0.6071 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -7.8601   -0.4672   -2.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 97104  0  0  0  0  0  0  0  0999 V2000
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    6.6166    0.5858    0.6050 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9464   -0.6385    1.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652307012117053D          

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  4 51  1  0  0  0  0
  5 52  1  1  0  0  0
  6 53  1  0  0  0  0
  6 54  1  0  0  0  0
  7 55  1  6  0  0  0
  8 56  1  0  0  0  0
 10 57  1  0  0  0  0
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 43 95  1  0  0  0  0
 43 96  1  0  0  0  0
 43 97  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001696

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C([H])([H])[C@]([H])(O[C@@]2([H])C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@@]([H])(C([H])([H])C([H])([H])[C@@]4([H])C([H])([H])C5=C(N([H])C6=C([H])C([H])=C7C(=O)[C@]8([H])[C@@]([H])(C([H])([H])C7=C56)C(OC8(C([H])([H])[H])C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])[C@]34C([H])([H])[H])[C@]12C([H])([H])[H])C(O[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C38H53NO5/c1-33(2,42)28-18-26(40)37(8)25-13-10-19-16-22-29-21-17-23-30(35(5,6)44-34(23,3)4)31(41)20(21)11-12-24(29)39-32(22)38(19,9)36(25,7)15-14-27(37)43-28/h11-12,19,23,25-28,30,39-40,42H,10,13-18H2,1-9H3/t19-,23+,25+,26+,27-,28-,30-,36-,37+,38+/m0/s1

> <INCHI_KEY>
LUBQWHCYCGWUJS-GARPVJMRSA-N

> <FORMULA>
C38H53NO5

> <MOLECULAR_WEIGHT>
603.844

> <EXACT_MASS>
603.392373811

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
97

> <JCHEM_AVERAGE_POLARIZABILITY>
72.15698394434908

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,6S,8S,10R,11R,12R,15S,21R,25R)-10-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,11,22,22,24,24-heptamethyl-7,23-dioxa-31-azaoctacyclo[15.14.0.0^{2,15}.0^{3,12}.0^{6,11}.0^{18,30}.0^{19,27}.0^{21,25}]hentriaconta-1(17),18,27,29-tetraen-26-one

> <ALOGPS_LOGP>
6.47

> <JCHEM_LOGP>
5.386712208666667

> <ALOGPS_LOGS>
-6.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.448975843058847

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.959641248311325

> <JCHEM_PKA_STRONGEST_BASIC>
-3.002719029207401

> <JCHEM_POLAR_SURFACE_AREA>
91.78

> <JCHEM_REFRACTIVITY>
172.12070000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.51e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,6S,8S,10R,11R,12R,15S,21R,25R)-10-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,11,22,22,24,24-heptamethyl-7,23-dioxa-31-azaoctacyclo[15.14.0.0^{2,15}.0^{3,12}.0^{6,11}.0^{18,30}.0^{19,27}.0^{21,25}]hentriaconta-1(17),18,27,29-tetraen-26-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 97104  0  0  0  0  0  0  0  0999 V2000
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 40 89  1  0
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 40 91  1  0
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 41 93  1  0
 41 94  1  0
 43 95  1  0
 43 96  1  0
 43 97  1  0
M  END

HEADER    PROTEIN                                 01-JUL-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-JUL-21         0                                  
HETATM    1  C   UNK     0       8.582  -0.472  -0.555  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.098   0.470   0.493  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.729   0.144   1.823  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.575   1.755   0.142  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.617   0.586   0.605  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.946  -0.639   1.192  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.321  -1.382   0.002  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.113  -2.704   0.236  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.220  -0.598  -0.607  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.262  -0.840  -2.114  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.666   0.871  -0.432  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.811   1.811  -1.203  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.397   1.425  -1.351  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.917   0.127  -0.874  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.331  -0.730  -1.993  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.894  -0.642  -0.002  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.380  -1.951   0.469  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.089  -1.750   1.282  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.166  -1.004   0.439  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.133  -0.543   1.063  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.579   0.385  -0.009  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.447   0.940  -0.627  0.00  0.00           C+0
HETATM   23  N   UNK     0      -0.829   1.783  -1.603  0.00  0.00           N+0
HETATM   24  C   UNK     0      -2.172   1.808  -1.657  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.010   2.521  -2.487  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.372   2.365  -2.327  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.908   1.526  -1.371  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.026   0.819  -0.548  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.649   0.954  -0.683  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.552  -0.110   0.503  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.931  -0.499   0.140  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.785   0.780   0.059  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.363   1.388  -1.221  0.00  0.00           C+0
HETATM   34  O   UNK     0      -7.153   1.759  -2.110  0.00  0.00           O+0
HETATM   35  C   UNK     0      -8.134   0.162   0.080  0.00  0.00           C+0
HETATM   36  C   UNK     0      -9.102   1.156   0.713  0.00  0.00           C+0
HETATM   37  C   UNK     0      -8.653  -0.127  -1.308  0.00  0.00           C+0
HETATM   38  O   UNK     0      -8.044  -0.998   0.848  0.00  0.00           O+0
HETATM   39  C   UNK     0      -6.723  -1.252   1.139  0.00  0.00           C+0
HETATM   40  C   UNK     0      -6.336  -0.834   2.538  0.00  0.00           C+0
HETATM   41  C   UNK     0      -6.470  -2.763   1.055  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.718   0.369   0.057  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.061   1.175   1.243  0.00  0.00           C+0
HETATM   44  O   UNK     0       6.008   0.994  -0.582  0.00  0.00           O+0
HETATM   45  H   UNK     0       8.145  -0.245  -1.547  0.00  0.00           H+0
HETATM   46  H   UNK     0       9.688  -0.276  -0.681  0.00  0.00           H+0
HETATM   47  H   UNK     0       8.519  -1.542  -0.277  0.00  0.00           H+0
HETATM   48  H   UNK     0       8.646  -0.915   2.103  0.00  0.00           H+0
HETATM   49  H   UNK     0       8.250   0.816   2.594  0.00  0.00           H+0
HETATM   50  H   UNK     0       9.800   0.487   1.791  0.00  0.00           H+0
HETATM   51  H   UNK     0       9.492   1.690  -0.245  0.00  0.00           H+0
HETATM   52  H   UNK     0       6.414   1.418   1.340  0.00  0.00           H+0
HETATM   53  H   UNK     0       5.135  -0.403   1.882  0.00  0.00           H+0
HETATM   54  H   UNK     0       6.680  -1.342   1.636  0.00  0.00           H+0
HETATM   55  H   UNK     0       6.175  -1.359  -0.752  0.00  0.00           H+0
HETATM   56  H   UNK     0       5.575  -3.050   1.022  0.00  0.00           H+0
HETATM   57  H   UNK     0       5.335  -1.096  -2.385  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.694  -1.728  -2.419  0.00  0.00           H+0
HETATM   59  H   UNK     0       4.065   0.068  -2.700  0.00  0.00           H+0
HETATM   60  H   UNK     0       4.440   1.081   0.659  0.00  0.00           H+0
HETATM   61  H   UNK     0       4.336   2.010  -2.187  0.00  0.00           H+0
HETATM   62  H   UNK     0       3.928   2.816  -0.686  0.00  0.00           H+0
HETATM   63  H   UNK     0       1.777   2.278  -0.933  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.154   1.494  -2.458  0.00  0.00           H+0
HETATM   65  H   UNK     0       0.229  -0.505  -2.135  0.00  0.00           H+0
HETATM   66  H   UNK     0       1.754  -0.440  -3.000  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.386  -1.797  -1.806  0.00  0.00           H+0
HETATM   68  H   UNK     0       2.927  -0.022   0.954  0.00  0.00           H+0
HETATM   69  H   UNK     0       3.090  -2.301   1.280  0.00  0.00           H+0
HETATM   70  H   UNK     0       2.304  -2.748  -0.256  0.00  0.00           H+0
HETATM   71  H   UNK     0       1.289  -1.384   2.288  0.00  0.00           H+0
HETATM   72  H   UNK     0       0.691  -2.800   1.411  0.00  0.00           H+0
HETATM   73  H   UNK     0      -0.111  -1.591  -0.446  0.00  0.00           H+0
HETATM   74  H   UNK     0      -0.972   0.062   1.972  0.00  0.00           H+0
HETATM   75  H   UNK     0      -1.748  -1.423   1.198  0.00  0.00           H+0
HETATM   76  H   UNK     0      -0.223   2.342  -2.238  0.00  0.00           H+0
HETATM   77  H   UNK     0      -2.609   3.198  -3.259  0.00  0.00           H+0
HETATM   78  H   UNK     0      -5.049   2.914  -2.967  0.00  0.00           H+0
HETATM   79  H   UNK     0      -4.445   0.349   1.491  0.00  0.00           H+0
HETATM   80  H   UNK     0      -3.929  -1.049   0.393  0.00  0.00           H+0
HETATM   81  H   UNK     0      -5.919  -0.954  -0.871  0.00  0.00           H+0
HETATM   82  H   UNK     0      -6.574   1.444   0.921  0.00  0.00           H+0
HETATM   83  H   UNK     0      -9.825   0.569   1.307  0.00  0.00           H+0
HETATM   84  H   UNK     0      -9.671   1.725  -0.043  0.00  0.00           H+0
HETATM   85  H   UNK     0      -8.549   1.893   1.349  0.00  0.00           H+0
HETATM   86  H   UNK     0      -9.390  -0.974  -1.241  0.00  0.00           H+0
HETATM   87  H   UNK     0      -9.215   0.724  -1.729  0.00  0.00           H+0
HETATM   88  H   UNK     0      -7.860  -0.467  -2.005  0.00  0.00           H+0
HETATM   89  H   UNK     0      -5.371  -1.324   2.777  0.00  0.00           H+0
HETATM   90  H   UNK     0      -6.176   0.261   2.611  0.00  0.00           H+0
HETATM   91  H   UNK     0      -7.092  -1.226   3.223  0.00  0.00           H+0
HETATM   92  H   UNK     0      -6.830  -3.186   0.112  0.00  0.00           H+0
HETATM   93  H   UNK     0      -5.379  -2.911   1.202  0.00  0.00           H+0
HETATM   94  H   UNK     0      -6.966  -3.217   1.945  0.00  0.00           H+0
HETATM   95  H   UNK     0       0.269   1.957   1.434  0.00  0.00           H+0
HETATM   96  H   UNK     0       1.198   0.649   2.184  0.00  0.00           H+0
HETATM   97  H   UNK     0       1.994   1.789   1.069  0.00  0.00           H+0
CONECT    1    2   45   46   47                                             
CONECT    2    1    3    4    5                                             
CONECT    3    2   48   49   50                                             
CONECT    4    2   51                                                       
CONECT    5    2    6   44   52                                             
CONECT    6    5    7   53   54                                             
CONECT    7    6    8    9   55                                             
CONECT    8    7   56                                                       
CONECT    9    7   10   11   16                                             
CONECT   10    9   57   58   59                                             
CONECT   11    9   12   44   60                                             
CONECT   12   11   13   61   62                                             
CONECT   13   12   14   63   64                                             
CONECT   14   13   15   16   42                                             
CONECT   15   14   65   66   67                                             
CONECT   16   14   17    9   68                                             
CONECT   17   16   18   69   70                                             
CONECT   18   17   19   71   72                                             
CONECT   19   18   20   42   73                                             
CONECT   20   19   21   74   75                                             
CONECT   21   20   22   29                                                  
CONECT   22   21   23   42                                                  
CONECT   23   22   24   76                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26   77                                                  
CONECT   26   25   27   78                                                  
CONECT   27   26   28   33                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28   21   24                                                  
CONECT   30   28   31   79   80                                             
CONECT   31   30   32   39   81                                             
CONECT   32   31   33   35   82                                             
CONECT   33   32   34   27                                                  
CONECT   34   33                                                            
CONECT   35   32   36   37   38                                             
CONECT   36   35   83   84   85                                             
CONECT   37   35   86   87   88                                             
CONECT   38   35   39                                                       
CONECT   39   38   40   41   31                                             
CONECT   40   39   89   90   91                                             
CONECT   41   39   92   93   94                                             
CONECT   42   22   43   19   14                                             
CONECT   43   42   95   96   97                                             
CONECT   44   11    5                                                       
CONECT   45    1                                                            
CONECT   46    1                                                            
CONECT   47    1                                                            
CONECT   48    3                                                            
CONECT   49    3                                                            
CONECT   50    3                                                            
CONECT   51    4                                                            
CONECT   52    5                                                            
CONECT   53    6                                                            
CONECT   54    6                                                            
CONECT   55    7                                                            
CONECT   56    8                                                            
CONECT   57   10                                                            
CONECT   58   10                                                            
CONECT   59   10                                                            
CONECT   60   11                                                            
CONECT   61   12                                                            
CONECT   62   12                                                            
CONECT   63   13                                                            
CONECT   64   13                                                            
CONECT   65   15                                                            
CONECT   66   15                                                            
CONECT   67   15                                                            
CONECT   68   16                                                            
CONECT   69   17                                                            
CONECT   70   17                                                            
CONECT   71   18                                                            
CONECT   72   18                                                            
CONECT   73   19                                                            
CONECT   74   20                                                            
CONECT   75   20                                                            
CONECT   76   23                                                            
CONECT   77   25                                                            
CONECT   78   26                                                            
CONECT   79   30                                                            
CONECT   80   30                                                            
CONECT   81   31                                                            
CONECT   82   32                                                            
CONECT   83   36                                                            
CONECT   84   36                                                            
CONECT   85   36                                                            
CONECT   86   37                                                            
CONECT   87   37                                                            
CONECT   88   37                                                            
CONECT   89   40                                                            
CONECT   90   40                                                            
CONECT   91   40                                                            
CONECT   92   41                                                            
CONECT   93   41                                                            
CONECT   94   41                                                            
CONECT   95   43                                                            
CONECT   96   43                                                            
CONECT   97   43                                                            
MASTER        0    0    0    0    0    0    0    0   97    0  208    0
END

RDKit          3D

97104  0  0  0  0  0  0  0  0999 V2000
    8.5820   -0.4715   -0.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0983    0.4704    0.4929 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7287    0.1439    1.8232 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5754    1.7551    0.1421 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6166    0.5858    0.6050 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9464   -0.6385    1.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3212   -1.3818    0.0015 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1127   -2.7041    0.2361 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2196   -0.5980   -0.6071 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2623   -0.8401   -2.1142 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6658    0.8711   -0.4322 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8112    1.8114   -1.2029 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3973    1.4245   -1.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9169    0.1268   -0.8744 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3309   -0.7295   -1.9927 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8937   -0.6422   -0.0020 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3803   -1.9507    0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0888   -1.7502    1.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1658   -1.0042    0.4386 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1332   -0.5428    1.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5794    0.3854   -0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4468    0.9399   -0.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8292    1.7827   -1.6035 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1723    1.8080   -1.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0095    2.5208   -2.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3717    2.3655   -2.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9077    1.5260   -1.3707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0258    0.8191   -0.5475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6488    0.9540   -0.6831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5518   -0.1099    0.5034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9310   -0.4987    0.1395 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7853    0.7802    0.0592 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3633    1.3879   -1.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1534    1.7587   -2.1101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1341    0.1624    0.0800 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.1021    1.1563    0.7128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6527   -0.1265   -1.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0441   -0.9976    0.8478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7234   -1.2522    1.1394 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3357   -0.8343    2.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4702   -2.7631    1.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7183    0.3686    0.0573 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0614    1.1754    1.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0084    0.9935   -0.5821 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1445   -0.2445   -1.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6881   -0.2762   -0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5188   -1.5421   -0.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6457   -0.9146    2.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2503    0.8161    2.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7995    0.4874    1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4915    1.6904   -0.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4137    1.4184    1.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1345   -0.4031    1.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6804   -1.3417    1.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1751   -1.3590   -0.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5748   -3.0495    1.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3347   -1.0958   -2.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6937   -1.7277   -2.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0648    0.0676   -2.7000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4398    1.0813    0.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3361    2.0095   -2.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9278    2.8160   -0.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7765    2.2783   -0.9334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1541    1.4944   -2.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2287   -0.5049   -2.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7542   -0.4395   -2.9996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3857   -1.7969   -1.8057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9267   -0.0217    0.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0898   -2.3008    1.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3040   -2.7480   -0.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2885   -1.3837    2.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6905   -2.7996    1.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1106   -1.5915   -0.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9721    0.0616    1.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7476   -1.4229    1.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2225    2.3425   -2.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6094    3.1976   -3.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0489    2.9145   -2.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4452    0.3493    1.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9293   -1.0488    0.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9192   -0.9541   -0.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5743    1.4435    0.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8251    0.5685    1.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6708    1.7247   -0.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5494    1.8933    1.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3898   -0.9744   -1.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2146    0.7241   -1.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8601   -0.4672   -2.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3713   -1.3236    2.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1758    0.2606    2.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0916   -1.2262    3.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8297   -3.1859    0.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3794   -2.9108    1.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9663   -3.2167    1.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2686    1.9569    1.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1976    0.6490    2.1844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9939    1.7885    1.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  6
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  6
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 35 36  1  1
 35 37  1  0
 35 38  1  0
 38 39  1  0
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 22 42  1  0
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 11 44  1  0
 44  5  1  0
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 42 19  1  0
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 29 21  1  0
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 33 27  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
  3 48  1  0
  3 49  1  0
  3 50  1  0
  4 51  1  0
  5 52  1  1
  6 53  1  0
  6 54  1  0
  7 55  1  6
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 43 97  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₃₈H₅₃NO₅

Average Mass

603.8440 Da

Monoisotopic Mass

603.39237 Da

IUPAC Name

(2S,3S,6S,8S,10R,11R,12R,15S,21R,25R)-10-hydroxy-8-(2-hydroxypropan-2-yl)-2,3,11,22,22,24,24-heptamethyl-7,23-dioxa-31-azaoctacyclo[15.14.0.0^{2,15}.0^{3,12}.0^{6,11}.0^{18,30}.0^{19,27}.0^{21,25}]hentriaconta-1(17),18,27,29-tetraen-26-one

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)(O)[C@@H]1C[C@@H](O)[C@]2(C)[C@H](CC[C@@]3(C)[C@H]2CC[C@H]2CC4=C(NC5=C4C4=C(C=C5)C(=O)[C@@H]5[C@@H](C4)C(C)(C)OC5(C)C)[C@]32C)O1

InChI Identifier

InChI=1S/C38H53NO5/c1-33(2,42)28-18-26(40)37(8)25-13-10-19-16-22-29-21-17-23-30(35(5,6)44-34(23,3)4)31(41)20(21)11-12-24(29)39-32(22)38(19,9)36(25,7)15-14-27(37)43-28/h11-12,19,23,25-28,30,39-40,42H,10,13-18H2,1-9H3/t19-,23+,25+,26+,27-,28-,30-,36-,37+,38+/m0/s1

InChI Key

LUBQWHCYCGWUJS-GARPVJMRSA-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
Lolium perenne	Plant	KNApSAcK
Neotyphodium	NPAtlas	10554283

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.47	ALOGPS
logP	5.39	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	13.96	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	91.78 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	172.12 m³·mol⁻¹	ChemAxon
Polarizability	72.16 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA000018

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

30790753

KEGG Compound ID

C20584

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72734310

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Munday-Finch SC, Wilkins AL, Miles CO: Isolation of Lolicine A, Lolicine B, Lolitriol, and Lolitrem N from Lolium perenne Infected with Neotyphodium lolii and Evidence for the Natural Occurrence of 31-Epilolitrem N and 31-Epilolitrem F. J Agric Food Chem. 1998 Feb 16;46(2):590-598. doi: 10.1021/jf9706787. [PubMed:10554283 ]

Showing NP-Card for Lolicine A (NP0001696)

MOL for NP0001696 (Lolicine A)

3D MOL for NP0001696 (Lolicine A)

3D SDF for NP0001696 (Lolicine A)

3D-SDF for NP0001696 (Lolicine A)

PDB for NP0001696 (Lolicine A)

3D PDB for NP0001696 (Lolicine A)

SMILES for NP0001696 (Lolicine A)

INCHI for NP0001696 (Lolicine A)

Structure for NP0001696 (Lolicine A)

3D Structure for NP0001696 (Lolicine A)