MiMeDB: Showing metabocard for Lokisin (MMDBc0019826)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 09:50:38 UTC

Update Date

2025-10-07 16:07:01 UTC

Metabolite ID

MMDBc0019826

Metabolite Identification

Common Name

Lokisin

Description

Lokisin is a cyclic lipopeptide belonging to the chemical class of nonribosomal peptides. Its chemical structure is characterized by a cyclic arrangement of amino acids, which is typical for lipopeptides, and it is produced by fluorescent Pseudomonas species through nonribosomal peptide synthetase (NRPS) pathways. Lokisin is involved in various biosynthetic gene clusters (BGCs), including a lokisin-like cluster that shows phylogenetic similarities to other transporters in the amphisin family (PMID:38033591 ). This compound has been identified alongside other metabolites such as pyrrolnitrin and phenazine-1-carboxylic acid (PMID:39601883 ). It plays a role in plant biocontrol, as evidenced by its ability to induce resistance against fungal pathogens in planta (PMID:31354771 ). Genetic studies indicate that mutation of the lokA gene, which encodes one of the NRPS genes for lokisin, results in a deficiency in fungal antagonism, highlighting its importance in defense mechanisms (PMID:32537904 ). Additionally, the presence of lokisin-like derivatives in related species suggests metabolic interactions and potential handoffs between different organisms (PMID:36215464 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152111502D          

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M  END


  Mrv1652305152111502D          

109109  0  0  1  0            999 V2000
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   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8592    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 53109  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0019826

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](O)(CCCCCCC)CC(O)=NC([H])(CC(C)C)C(O)=NC([H])(CC(O)=O)C(O)=N[C@@]1([H])C(O)=NC([H])(CC(C)C)C(O)=NC([H])(CC(C)C)C(O)=N[C@]([H])(CO)C(O)=NC([H])(CC(C)C)C(O)=N[C@]([H])(CO)C(O)=NC([H])(CC(C)C)C(O)=N[C@]([H])(C(O)=NC([H])(CC(O)=O)C(=O)O[C@@]1([H])C)[C@@]([H])(C)CC

> <INCHI_IDENTIFIER>
InChI=1S/C64H111N11O20/c1-15-17-18-19-20-21-39(78)27-49(79)65-40(22-32(3)4)54(84)69-45(28-50(80)81)59(89)75-53-38(14)95-64(94)46(29-51(82)83)71-62(92)52(37(13)16-2)74-58(88)44(26-36(11)12)68-61(91)48(31-77)73-57(87)42(24-34(7)8)67-60(90)47(30-76)72-56(86)41(23-33(5)6)66-55(85)43(25-35(9)10)70-63(53)93/h32-48,52-53,76-78H,15-31H2,1-14H3,(H,65,79)(H,66,85)(H,67,90)(H,68,91)(H,69,84)(H,70,93)(H,71,92)(H,72,86)(H,73,87)(H,74,88)(H,75,89)(H,80,81)(H,82,83)/t37-,38-,39+,40?,41?,42?,43?,44?,45?,46?,47+,48+,52-,53+/m0/s1

> <INCHI_KEY>
GHXLBZVIYYOQOC-ORYVKZIQSA-N

> <FORMULA>
C64H111N11O20

> <MOLECULAR_WEIGHT>
1354.649

> <EXACT_MASS>
1353.800685018

> <JCHEM_ACCEPTOR_COUNT>
30

> <JCHEM_ATOM_COUNT>
206

> <JCHEM_AVERAGE_POLARIZABILITY>
146.85407783615528

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
16

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(6S,12R,18R,27R,28S)-6-[(2S)-butan-2-yl]-3-(carboxymethyl)-5,8,11,14,17,20,23,26-octahydroxy-12,18-bis(hydroxymethyl)-28-methyl-9,15,21,24-tetrakis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16,19,22,25-octaazacyclooctacosa-4,7,10,13,16,19,22,25-octaen-27-yl]-C-hydroxycarbonimidoyl}-3-[(2-{[(3R)-1,3-dihydroxydecylidene]amino}-1-hydroxy-4-methylpentylidene)amino]propanoic acid

> <ALOGPS_LOGP>
1.94

> <JCHEM_LOGP>
9.73160324433334

> <ALOGPS_LOGS>
-4.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.984004009172028

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.578376988385384

> <JCHEM_POLAR_SURFACE_AREA>
520.0800000000002

> <JCHEM_REFRACTIVITY>
346.59629999999987

> <JCHEM_ROTATABLE_BOND_COUNT>
31

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(6S,12R,18R,27R,28S)-6-[(2S)-butan-2-yl]-3-(carboxymethyl)-5,8,11,14,17,20,23,26-octahydroxy-12,18-bis(hydroxymethyl)-28-methyl-9,15,21,24-tetrakis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16,19,22,25-octaazacyclooctacosa-4,7,10,13,16,19,22,25-octaen-27-yl]-C-hydroxycarbonimidoyl}-3-[(2-{[(3R)-1,3-dihydroxydecylidene]amino}-1-hydroxy-4-methylpentylidene)amino]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0     -18.672  -6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.338  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.670  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003   5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.337   3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.532   0.161   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -16.004  -6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -13.337  -6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.004  -1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.669   3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.003  -3.850   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.670   3.850   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   65  N   UNK     0      -5.335  -6.160   0.000  0.00  0.00           N+0
HETATM   66  N   UNK     0       6.668  -2.310   0.000  0.00  0.00           N+0
HETATM   67  N   UNK     0      14.670  -2.310   0.000  0.00  0.00           N+0
HETATM   68  N   UNK     0      12.003   2.310   0.000  0.00  0.00           N+0
HETATM   69  N   UNK     0      -2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   70  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   71  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
HETATM   72  N   UNK     0      10.669  -3.080   0.000  0.00  0.00           N+0
HETATM   73  N   UNK     0      16.004   1.540   0.000  0.00  0.00           N+0
HETATM   74  N   UNK     0       8.002   1.540   0.000  0.00  0.00           N+0
HETATM   75  N   UNK     0      -0.000  -1.540   0.000  0.00  0.00           N+0
HETATM   76  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   77  O   UNK     0      16.004   4.620   0.000  0.00  0.00           O+0
HETATM   78  O   UNK     0      -9.336  -3.850   0.000  0.00  0.00           O+0
HETATM   79  O   UNK     0      -6.668  -3.850   0.000  0.00  0.00           O+0
HETATM   80  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   81  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   82  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM   83  O   UNK     0       5.335   3.080   0.000  0.00  0.00           O+0
HETATM   84  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   85  O   UNK     0       4.430  -4.326   0.000  0.00  0.00           O+0
HETATM   86  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   87  O   UNK     0      17.338  -0.770   0.000  0.00  0.00           O+0
HETATM   88  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   89  O   UNK     0      -2.239   0.476   0.000  0.00  0.00           O+0
HETATM   90  O   UNK     0      13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   91  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
HETATM   92  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   93  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   94  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   95  O   UNK     0      -0.000   1.540   0.000  0.00  0.00           O+0
HETATM   96  H   UNK     0       6.668   5.390   0.000  0.00  0.00           H+0
HETATM   97  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   98  H   UNK     0      -9.336  -6.930   0.000  0.00  0.00           H+0
HETATM   99  H   UNK     0      -2.667  -4.620   0.000  0.00  0.00           H+0
HETATM  100  H   UNK     0       6.668  -3.850   0.000  0.00  0.00           H+0
HETATM  101  H   UNK     0      13.337  -1.540   0.000  0.00  0.00           H+0
HETATM  102  H   UNK     0       4.001  -0.770   0.000  0.00  0.00           H+0
HETATM  103  H   UNK     0      10.669   0.000   0.000  0.00  0.00           H+0
HETATM  104  H   UNK     0      -2.667   0.000   0.000  0.00  0.00           H+0
HETATM  105  H   UNK     0       3.437   0.206   0.000  0.00  0.00           H+0
HETATM  106  H   UNK     0      11.233  -0.976   0.000  0.00  0.00           H+0
HETATM  107  H   UNK     0      16.004   3.080   0.000  0.00  0.00           H+0
HETATM  108  H   UNK     0       8.002   3.080   0.000  0.00  0.00           H+0
HETATM  109  H   UNK     0       2.874  -0.770   0.000  0.00  0.00           H+0
CONECT    1   15                                                            
CONECT    2   16                                                            
CONECT    3   32                                                            
CONECT    4   32                                                            
CONECT    5   33                                                            
CONECT    6   33                                                            
CONECT    7   34                                                            
CONECT    8   34                                                            
CONECT    9   35                                                            
CONECT   10   35                                                            
CONECT   11   36                                                            
CONECT   12   36                                                            
CONECT   13   37                                                            
CONECT   14   38                                                            
CONECT   15    1   17                                                       
CONECT   16    2   37                                                       
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   39                                                       
CONECT   22   32   40                                                       
CONECT   23   33   41                                                       
CONECT   24   34   42                                                       
CONECT   25   35   43                                                       
CONECT   26   36   44                                                       
CONECT   27   39   49                                                       
CONECT   28   45   50                                                       
CONECT   29   46   51                                                       
CONECT   30   47   76                                                       
CONECT   31   48   77                                                       
CONECT   32    3    4   22                                                  
CONECT   33    5    6   23                                                  
CONECT   34    7    8   24                                                  
CONECT   35    9   10   25                                                  
CONECT   36   11   12   26                                                  
CONECT   37   13   16   52   96                                             
CONECT   38   14   53   95   97                                             
CONECT   39   21   27   78   98                                             
CONECT   40   22   54   65   99                                             
CONECT   41   23   56   66  100                                             
CONECT   42   24   57   67  101                                             
CONECT   43   25   55   70  102                                             
CONECT   44   26   58   68  103                                             
CONECT   45   28   59   69  104                                             
CONECT   46   29   64   71  105                                             
CONECT   47   30   60   72  106                                             
CONECT   48   31   61   73  107                                             
CONECT   49   27   65   79                                                  
CONECT   50   28   80   81                                                  
CONECT   51   29   82   83                                                  
CONECT   52   37   62   74  108                                             
CONECT   53   38   63   75  109                                             
CONECT   54   40   69   84                                                  
CONECT   55   43   66   85                                                  
CONECT   56   41   72   86                                                  
CONECT   57   42   73   87                                                  
CONECT   58   44   74   88                                                  
CONECT   59   45   75   89                                                  
CONECT   60   47   67   90                                                  
CONECT   61   48   68   91                                                  
CONECT   62   52   71   92                                                  
CONECT   63   53   70   93                                                  
CONECT   64   46   94   95                                                  
CONECT   65   40   49                                                       
CONECT   66   41   55                                                       
CONECT   67   42   60                                                       
CONECT   68   44   61                                                       
CONECT   69   45   54                                                       
CONECT   70   43   63                                                       
CONECT   71   46   62                                                       
CONECT   72   47   56                                                       
CONECT   73   48   57                                                       
CONECT   74   52   58                                                       
CONECT   75   53   59                                                       
CONECT   76   30                                                            
CONECT   77   31                                                            
CONECT   78   39                                                            
CONECT   79   49                                                            
CONECT   80   50                                                            
CONECT   81   50                                                            
CONECT   82   51                                                            
CONECT   83   51                                                            
CONECT   84   54                                                            
CONECT   85   55                                                            
CONECT   86   56                                                            
CONECT   87   57                                                            
CONECT   88   58                                                            
CONECT   89   59                                                            
CONECT   90   60                                                            
CONECT   91   61                                                            
CONECT   92   62                                                            
CONECT   93   63                                                            
CONECT   94   64                                                            
CONECT   95   38   64                                                       
CONECT   96   37                                                            
CONECT   97   38                                                            
CONECT   98   39                                                            
CONECT   99   40                                                            
CONECT  100   41                                                            
CONECT  101   42                                                            
CONECT  102   43                                                            
CONECT  103   44                                                            
CONECT  104   45                                                            
CONECT  105   46                                                            
CONECT  106   47                                                            
CONECT  107   48                                                            
CONECT  108   52                                                            
CONECT  109   53                                                            
MASTER        0    0    0    0    0    0    0    0  109    0  218    0
END

Synonyms

Not Available

Molecular Formula

C₆₄H₁₁₁N₁₁O₂₀

Average Mass

1354.649

Monoisotopic Mass

1353.800685018

IUPAC Name

3-{[(6S,12R,18R,27R,28S)-6-[(2S)-butan-2-yl]-3-(carboxymethyl)-5,8,11,14,17,20,23,26-octahydroxy-12,18-bis(hydroxymethyl)-28-methyl-9,15,21,24-tetrakis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16,19,22,25-octaazacyclooctacosa-4,7,10,13,16,19,22,25-octaen-27-yl]-C-hydroxycarbonimidoyl}-3-[(2-{[(3R)-1,3-dihydroxydecylidene]amino}-1-hydroxy-4-methylpentylidene)amino]propanoic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(CCCCCCC)CC(O)=NC([H])(CC(C)C)C(O)=NC([H])(CC(O)=O)C(O)=N[C@@]1([H])C(O)=NC([H])(CC(C)C)C(O)=NC([H])(CC(C)C)C(O)=N[C@]([H])(CO)C(O)=NC([H])(CC(C)C)C(O)=N[C@]([H])(CO)C(O)=NC([H])(CC(C)C)C(O)=N[C@]([H])(C(O)=NC([H])(CC(O)=O)C(=O)O[C@@]1([H])C)[C@@]([H])(C)CC

InChI Identifier

InChI=1S/C64H111N11O20/c1-15-17-18-19-20-21-39(78)27-49(79)65-40(22-32(3)4)54(84)69-45(28-50(80)81)59(89)75-53-38(14)95-64(94)46(29-51(82)83)71-62(92)52(37(13)16-2)74-58(88)44(26-36(11)12)68-61(91)48(31-77)73-57(87)42(24-34(7)8)67-60(90)47(30-76)72-56(86)41(23-33(5)6)66-55(85)43(25-35(9)10)70-63(53)93/h32-48,52-53,76-78H,15-31H2,1-14H3,(H,65,79)(H,66,85)(H,67,90)(H,68,91)(H,69,84)(H,70,93)(H,71,92)(H,72,86)(H,73,87)(H,74,88)(H,75,89)(H,80,81)(H,82,83)/t37-,38-,39+,40?,41?,42?,43?,44?,45?,46?,47+,48+,52-,53+/m0/s1

InChI Key

GHXLBZVIYYOQOC-ORYVKZIQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic depsipeptides

Alternative Parents

Substituents

Cyclic depsipeptide
Macrolactam
Alpha-amino acid ester
Alpha-amino acid or derivatives
Tricarboxylic acid or derivatives
Cyclic carboximidic acid
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Carboxylic acid
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.022 g/L	ALOGPS
logP	1.94	ALOGPS
logP	9.73	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	2.58	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	30	ChemAxon
Hydrogen Donor Count	16	ChemAxon
Polar Surface Area	520.08 Å²	ChemAxon
Rotatable Bond Count	31	ChemAxon
Refractivity	346.6 m³·mol⁻¹	ChemAxon
Polarizability	146.85 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (void)	2025-10-23	408.1
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	227.5
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	1159.4
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	764.5
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	941.2
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	76.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	3662.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	150.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	299.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	396.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	60.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	139.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	275.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	10.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	57.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	242.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	694.4
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	2531.9
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1559.2

Retention Indices

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human feces; Human	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78445356

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139588598

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Lokisin (MMDBc0019826)

MOL for #<Metabolite:0x00007f2e3904b898>

3D MOL for #<Metabolite:0x00007f2e3904b898>

3D SDF for #<Metabolite:0x00007f2e3904b898>

3D-SDF for #<Metabolite:0x00007f2e3904b898>

PDB for #<Metabolite:0x00007f2e3904b898>

3D PDB for #<Metabolite:0x00007f2e3904b898>

SMILES for #<Metabolite:0x00007f2e3904b898>

INCHI for #<Metabolite:0x00007f2e3904b898>

Structure for #<Metabolite:0x00007f2e3904b898>

3D Structure for #<Metabolite:0x00007f2e3904b898>