Showing metabocard for Homocereulide (MMDBc0011907)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-05-15 03:36:00 UTC
Update Date2025-10-07 16:05:55 UTC
Metabolite IDMMDBc0011907
Metabolite Identification
Common NameHomocereulide
DescriptionHomocereulide is a cyclic dodecadepsipeptide belonging to the class of microbial metabolites. Isolated from the marine bacterium Bacillus cereus, it is an analog of the emetic toxin cereulide and exhibits notable biological activity. The chemical structure of homocereulide comprises l-O-Val-l-Val-d-O-Leu-d-Ala and l-O-allo-Ile-d-Val-d-O-Leu-d-Ala units, as confirmed by NMR spectroscopy and LC-MS analysis, which demonstrated consistency with natural products (PMID:30665680 ). The synthesis of homocereulide was achieved through liquid phase fragment condensation, allowing for a detailed examination of its properties (PMID:30665680 ). In functional assays, homocereulide displayed higher toxicity in HEp-2 cells at a concentration of 1.39 nM compared to cereulide, which exhibited toxicity at 3.95 nM (PMID:30665680 ). This suggests that while cereulide is the predominant component in broth cultures, homocereulide may also play a significant role in the biological effects associated with B. cereus (PMID:30665680 ). The exploration of homocereulide's structure and effects contributes to our understanding of the toxicological profiles of bacterial metabolites.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f2ac8745b18>


  Mrv1652305152105362D          

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M  END
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3D MOL for #<Metabolite:0x00007f2ac8745b18>

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3D SDF for #<Metabolite:0x00007f2ac8745b18>

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    1.6500   -7.5868    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
MMDBc0011907

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](C)(CC)C1([H])OC(=O)C([H])(C)N=C(O)C([H])(CC(C)C)OC(=O)C([H])(N=C(O)C([H])(OC(=O)C([H])(C)N=C(O)C([H])(CC(C)C)OC(=O)C([H])(N=C(O)C([H])(OC(=O)C([H])(C)N=C(O)C([H])(CC(C)C)OC(=O)C([H])(N=C1O)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C58H98N6O18/c1-22-34(18)46-52(70)64-43(31(12)13)58(76)79-39(24-27(4)5)48(66)60-36(20)54(72)81-44(32(14)15)50(68)62-41(29(8)9)56(74)77-38(23-26(2)3)47(65)59-35(19)53(71)80-45(33(16)17)51(69)63-42(30(10)11)57(75)78-40(25-28(6)7)49(67)61-37(21)55(73)82-46/h26-46H,22-25H2,1-21H3,(H,59,65)(H,60,66)(H,61,67)(H,62,68)(H,63,69)(H,64,70)/t34-,35?,36?,37?,38?,39?,40?,41?,42?,43?,44?,45?,46?/m0/s1

> <INCHI_KEY>
CFCIXEUIPLBOOH-SORGKVSXSA-N

> <FORMULA>
C58H98N6O18

> <MOLECULAR_WEIGHT>
1167.446

> <EXACT_MASS>
1166.69376034

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
180

> <JCHEM_AVERAGE_POLARIZABILITY>
125.86369425702773

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-[(2S)-butan-2-yl]-5,11,17,23,29,35-hexahydroxy-9,21,33-trimethyl-12,24,36-tris(2-methylpropyl)-3,15,18,27,30-pentakis(propan-2-yl)-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriaconta-4,10,16,22,28,34-hexaene-2,8,14,20,26,32-hexone

> <ALOGPS_LOGP>
4.36

> <JCHEM_LOGP>
12.386230879999998

> <ALOGPS_LOGS>
-5.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.1380302809705594

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.745961335374624

> <JCHEM_PKA_STRONGEST_BASIC>
0.7757355111443864

> <JCHEM_POLAR_SURFACE_AREA>
353.34000000000003

> <JCHEM_REFRACTIVITY>
298.59559999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.02e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(2S)-butan-2-yl]-5,11,17,23,29,35-hexahydroxy-3,15,18,27,30-pentaisopropyl-9,21,33-trimethyl-12,24,36-tris(2-methylpropyl)-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriaconta-4,10,16,22,28,34-hexaene-2,8,14,20,26,32-hexone

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for #<Metabolite:0x00007f2ac8745b18>
Download
PDB for #<Metabolite:0x00007f2ac8745b18>
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       2.310 -18.163   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.770   4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.057 -13.956   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.057 -11.288   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.137 -11.288   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.827 -12.622   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.105  -1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.771   0.976   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.185  -4.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.518  -6.311   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.770 -15.908   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.437 -15.908   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.057  -5.541   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.057  -2.874   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.517  -0.206   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.827  -1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.850 -15.496   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.644   0.976   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -7.645  -8.621   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.311 -13.598   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.540 -16.829   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.747 -12.622   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.827  -9.955   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   2.667   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -7.287 -12.622   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.597 -11.288   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.771  -0.564   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.185  -5.541   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.104 -15.138   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -7.287  -4.207   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.287  -1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.310 -15.496   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -6.311  -7.851   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.977 -12.828   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      -4.977 -11.288   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.287  -9.955   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -3.437  -1.334   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       7.851  -6.311   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -2.104 -13.598   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -5.747  -4.207   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       6.517  -2.874   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       1.540 -14.162   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       1.540  -0.000   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -5.747  -9.955   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       6.517 -11.288   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -4.977  -2.874   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       7.287  -4.207   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       0.000 -14.162   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       4.977  -1.334   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -6.311  -6.311   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       3.644 -13.598   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      -2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       7.851  -7.851   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -3.437 -12.828   0.000  0.00  0.00           C+0
HETATM   59  N   UNK     0       2.310  -1.334   0.000  0.00  0.00           N+0
HETATM   60  N   UNK     0      -4.977  -8.621   0.000  0.00  0.00           N+0
HETATM   61  N   UNK     0       4.977 -11.288   0.000  0.00  0.00           N+0
HETATM   62  N   UNK     0      -3.437  -2.874   0.000  0.00  0.00           N+0
HETATM   63  N   UNK     0       6.517  -5.541   0.000  0.00  0.00           N+0
HETATM   64  N   UNK     0      -0.770 -12.828   0.000  0.00  0.00           N+0
HETATM   65  O   UNK     0       2.310   1.334   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0      -7.287  -9.955   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0       7.287 -12.622   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0      -6.384  -2.247   0.000  0.00  0.00           O+0
HETATM   69  O   UNK     0       8.533  -3.302   0.000  0.00  0.00           O+0
HETATM   70  O   UNK     0       0.161 -15.694   0.000  0.00  0.00           O+0
HETATM   71  O   UNK     0       5.604   0.073   0.000  0.00  0.00           O+0
HETATM   72  O   UNK     0      -7.843  -6.472   0.000  0.00  0.00           O+0
HETATM   73  O   UNK     0       4.549 -14.844   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0      -2.104   0.976   0.000  0.00  0.00           O+0
HETATM   75  O   UNK     0       9.185  -8.621   0.000  0.00  0.00           O+0
HETATM   76  O   UNK     0      -4.771 -13.598   0.000  0.00  0.00           O+0
HETATM   77  O   UNK     0      -0.770  -1.334   0.000  0.00  0.00           O+0
HETATM   78  O   UNK     0       6.517  -8.621   0.000  0.00  0.00           O+0
HETATM   79  O   UNK     0      -3.437 -11.288   0.000  0.00  0.00           O+0
HETATM   80  O   UNK     0       4.977  -2.874   0.000  0.00  0.00           O+0
HETATM   81  O   UNK     0      -4.977  -5.541   0.000  0.00  0.00           O+0
HETATM   82  O   UNK     0       2.310 -12.828   0.000  0.00  0.00           O+0
HETATM   83  H   UNK     0       3.080 -16.829   0.000  0.00  0.00           H+0
HETATM   84  H   UNK     0       4.977   0.206   0.000  0.00  0.00           H+0
HETATM   85  H   UNK     0      -6.311  -9.391   0.000  0.00  0.00           H+0
HETATM   86  H   UNK     0       6.311 -12.058   0.000  0.00  0.00           H+0
HETATM   87  H   UNK     0      -1.540   0.000   0.000  0.00  0.00           H+0
HETATM   88  H   UNK     0      -4.207 -12.622   0.000  0.00  0.00           H+0
HETATM   89  H   UNK     0       8.057  -8.621   0.000  0.00  0.00           H+0
HETATM   90  H   UNK     0      -4.771  -2.104   0.000  0.00  0.00           H+0
HETATM   91  H   UNK     0       7.851  -4.771   0.000  0.00  0.00           H+0
HETATM   92  H   UNK     0      -0.770 -14.368   0.000  0.00  0.00           H+0
HETATM   93  H   UNK     0      -6.517  -5.541   0.000  0.00  0.00           H+0
HETATM   94  H   UNK     0       5.747  -1.540   0.000  0.00  0.00           H+0
HETATM   95  H   UNK     0       3.080 -14.162   0.000  0.00  0.00           H+0
CONECT    1   22                                                            
CONECT    2   26                                                            
CONECT    3   26                                                            
CONECT    4   27                                                            
CONECT    5   27                                                            
CONECT    6   28                                                            
CONECT    7   28                                                            
CONECT    8   29                                                            
CONECT    9   29                                                            
CONECT   10   30                                                            
CONECT   11   30                                                            
CONECT   12   31                                                            
CONECT   13   31                                                            
CONECT   14   32                                                            
CONECT   15   32                                                            
CONECT   16   33                                                            
CONECT   17   33                                                            
CONECT   18   34                                                            
CONECT   19   35                                                            
CONECT   20   36                                                            
CONECT   21   37                                                            
CONECT   22    1   34                                                       
CONECT   23   26   38                                                       
CONECT   24   27   39                                                       
CONECT   25   28   40                                                       
CONECT   26    2    3   23                                                  
CONECT   27    4    5   24                                                  
CONECT   28    6    7   25                                                  
CONECT   29    8    9   41                                                  
CONECT   30   10   11   42                                                  
CONECT   31   12   13   43                                                  
CONECT   32   14   15   44                                                  
CONECT   33   16   17   45                                                  
CONECT   34   18   22   46   83                                             
CONECT   35   19   53   59   84                                             
CONECT   36   20   54   60   85                                             
CONECT   37   21   55   61   86                                             
CONECT   38   23   47   77   87                                             
CONECT   39   24   48   79   88                                             
CONECT   40   25   49   78   89                                             
CONECT   41   29   56   62   90                                             
CONECT   42   30   57   63   91                                             
CONECT   43   31   58   64   92                                             
CONECT   44   32   50   81   93                                             
CONECT   45   33   51   80   94                                             
CONECT   46   34   52   82   95                                             
CONECT   47   38   59   65                                                  
CONECT   48   39   60   66                                                  
CONECT   49   40   61   67                                                  
CONECT   50   44   62   68                                                  
CONECT   51   45   63   69                                                  
CONECT   52   46   64   70                                                  
CONECT   53   35   71   80                                                  
CONECT   54   36   72   81                                                  
CONECT   55   37   73   82                                                  
CONECT   56   41   74   77                                                  
CONECT   57   42   75   78                                                  
CONECT   58   43   76   79                                                  
CONECT   59   35   47                                                       
CONECT   60   36   48                                                       
CONECT   61   37   49                                                       
CONECT   62   41   50                                                       
CONECT   63   42   51                                                       
CONECT   64   43   52                                                       
CONECT   65   47                                                            
CONECT   66   48                                                            
CONECT   67   49                                                            
CONECT   68   50                                                            
CONECT   69   51                                                            
CONECT   70   52                                                            
CONECT   71   53                                                            
CONECT   72   54                                                            
CONECT   73   55                                                            
CONECT   74   56                                                            
CONECT   75   57                                                            
CONECT   76   58                                                            
CONECT   77   38   56                                                       
CONECT   78   40   57                                                       
CONECT   79   39   58                                                       
CONECT   80   45   53                                                       
CONECT   81   44   54                                                       
CONECT   82   46   55                                                       
CONECT   83   34                                                            
CONECT   84   35                                                            
CONECT   85   36                                                            
CONECT   86   37                                                            
CONECT   87   38                                                            
CONECT   88   39                                                            
CONECT   89   40                                                            
CONECT   90   41                                                            
CONECT   91   42                                                            
CONECT   92   43                                                            
CONECT   93   44                                                            
CONECT   94   45                                                            
CONECT   95   46                                                            
MASTER        0    0    0    0    0    0    0    0   95    0  190    0
END

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3D PDB for #<Metabolite:0x00007f2ac8745b18>
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SMILES for #<Metabolite:0x00007f2ac8745b18>
[H][C@](C)(CC)C1([H])OC(=O)C([H])(C)N=C(O)C([H])(CC(C)C)OC(=O)C([H])(N=C(O)C([H])(OC(=O)C([H])(C)N=C(O)C([H])(CC(C)C)OC(=O)C([H])(N=C(O)C([H])(OC(=O)C([H])(C)N=C(O)C([H])(CC(C)C)OC(=O)C([H])(N=C1O)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C
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INCHI for #<Metabolite:0x00007f2ac8745b18>
InChI=1S/C58H98N6O18/c1-22-34(18)46-52(70)64-43(31(12)13)58(76)79-39(24-27(4)5)48(66)60-36(20)54(72)81-44(32(14)15)50(68)62-41(29(8)9)56(74)77-38(23-26(2)3)47(65)59-35(19)53(71)80-45(33(16)17)51(69)63-42(30(10)11)57(75)78-40(25-28(6)7)49(67)61-37(21)55(73)82-46/h26-46H,22-25H2,1-21H3,(H,59,65)(H,60,66)(H,61,67)(H,62,68)(H,63,69)(H,64,70)/t34-,35?,36?,37?,38?,39?,40?,41?,42?,43?,44?,45?,46?/m0/s1
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SynonymsNot Available
Molecular FormulaC58H98N6O18
Average Mass1167.446
Monoisotopic Mass1166.69376034
IUPAC Name6-[(2S)-butan-2-yl]-5,11,17,23,29,35-hexahydroxy-9,21,33-trimethyl-12,24,36-tris(2-methylpropyl)-3,15,18,27,30-pentakis(propan-2-yl)-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriaconta-4,10,16,22,28,34-hexaene-2,8,14,20,26,32-hexone
Traditional Name6-[(2S)-butan-2-yl]-5,11,17,23,29,35-hexahydroxy-3,15,18,27,30-pentaisopropyl-9,21,33-trimethyl-12,24,36-tris(2-methylpropyl)-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriaconta-4,10,16,22,28,34-hexaene-2,8,14,20,26,32-hexone
CAS Registry NumberNot Available
SMILES
[H][C@](C)(CC)C1([H])OC(=O)C([H])(C)N=C(O)C([H])(CC(C)C)OC(=O)C([H])(N=C(O)C([H])(OC(=O)C([H])(C)N=C(O)C([H])(CC(C)C)OC(=O)C([H])(N=C(O)C([H])(OC(=O)C([H])(C)N=C(O)C([H])(CC(C)C)OC(=O)C([H])(N=C1O)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C
InChI Identifier
InChI=1S/C58H98N6O18/c1-22-34(18)46-52(70)64-43(31(12)13)58(76)79-39(24-27(4)5)48(66)60-36(20)54(72)81-44(32(14)15)50(68)62-41(29(8)9)56(74)77-38(23-26(2)3)47(65)59-35(19)53(71)80-45(33(16)17)51(69)63-42(30(10)11)57(75)78-40(25-28(6)7)49(67)61-37(21)55(73)82-46/h26-46H,22-25H2,1-21H3,(H,59,65)(H,60,66)(H,61,67)(H,62,68)(H,63,69)(H,64,70)/t34-,35?,36?,37?,38?,39?,40?,41?,42?,43?,44?,45?,46?/m0/s1
InChI KeyCFCIXEUIPLBOOH-SORGKVSXSA-N