MiMeDB: Showing metabocard for Moiramide B (MMDBc0011224)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 03:09:39 UTC

Update Date

2025-10-07 16:05:50 UTC

Metabolite ID

MMDBc0011224

Metabolite Identification

Common Name

Moiramide B

Description

Moiramide B is a peptide-polyketide hybrid belonging to the chemical class of diketopiperazines, derived from bacterial sources. This compound exhibits significant antibiotic activity, particularly as an inhibitor of the carboxyltransferase component of acetyl-CoA carboxylase, a crucial enzyme in fatty acid synthesis. Moiramide B demonstrates strong antibacterial effects against gram-positive bacteria such as Bacillus subtilis, while showing weaker activity against gram-negative bacteria (PMID:36883965 ). Its structural uniqueness includes an unsaturated diketopiperazine framework, which presents challenges for optimization due to the narrow structure-activity relationship of its pseudopeptide unit (PMID:36883965 ). The compound has been the subject of various studies, including the synthesis of derivatives aimed at enhancing its biological activity (PMID:38864222 ). Notably, moiramide B is part of a select group of natural products that inhibit bacterial growth by targeting the Acyl Carrier Protein (ACP) system, alongside other compounds like andrimid and thailandamide (PMID:29975047 ). Structural studies have further elucidated its mechanism of action, providing insights into its binding interactions with bacterial enzymes (PMID:27471863 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152105092D          

 41 42  0  0  1  0            999 V2000
   -5.8225    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    8.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    8.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4888    5.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1080    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3935    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5356    9.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6791    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2501    9.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    9.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2501    8.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    8.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6791    6.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    6.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    8.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041    5.5178    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5356    8.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5356    7.2402    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9646    7.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067    7.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    6.0027    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3222    7.2402    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0367    6.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492    4.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693    5.5178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2501    6.8277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    6.8277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242    4.7331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9646    8.0652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067    8.0652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    7.2402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341    4.0657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846    5.7727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1080    6.8277    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3935    4.7652    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9646    5.5902    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3935    7.2402    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8332    6.3326    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    7.6527    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3016    6.3772    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    7.6527    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
 13  8  2  0  0  0  0
 15  2  1  0  0  0  0
 15  3  1  0  0  0  0
 16  4  1  6  0  0  0
 17 11  2  0  0  0  0
 17 12  1  0  0  0  0
 18 14  1  0  0  0  0
 18 17  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 16  1  0  0  0  0
 22 15  1  0  0  0  0
 21 23  1  1  0  0  0
 23 22  1  0  0  0  0
 24 16  1  0  0  0  0
 25 21  1  0  0  0  0
 18 26  1  1  0  0  0
 26 19  2  0  0  0  0
 27 20  2  0  0  0  0
 22 27  1  6  0  0  0
 28 24  2  0  0  0  0
 28 25  1  0  0  0  0
 19 29  1  4  0  0  0
 20 30  1  4  0  0  0
 31 23  2  0  0  0  0
 32 24  1  0  0  0  0
 33 25  2  0  0  0  0
 34  5  1  0  0  0  0
 35  6  1  0  0  0  0
 36  8  1  0  0  0  0
 37 13  1  0  0  0  0
 16 38  1  1  0  0  0
 18 39  1  1  0  0  0
 21 40  1  6  0  0  0
 22 41  1  6  0  0  0
M  END


  Mrv1652305152105092D          

 41 42  0  0  1  0            999 V2000
   -5.8225    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    8.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    8.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4888    5.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1080    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3935    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5356    9.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6791    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2501    9.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    9.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2501    8.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    8.4777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6791    6.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    6.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    8.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041    5.5178    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5356    8.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5356    7.2402    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9646    7.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067    7.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    6.0027    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3222    7.2402    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0367    6.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492    4.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693    5.5178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2501    6.8277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    6.8277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242    4.7331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9646    8.0652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067    8.0652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    7.2402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341    4.0657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846    5.7727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1080    6.8277    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3935    4.7652    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9646    5.5902    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3935    7.2402    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8332    6.3326    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    7.6527    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3016    6.3772    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    7.6527    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
 13  8  2  0  0  0  0
 15  2  1  0  0  0  0
 15  3  1  0  0  0  0
 16  4  1  6  0  0  0
 17 11  2  0  0  0  0
 17 12  1  0  0  0  0
 18 14  1  0  0  0  0
 18 17  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 16  1  0  0  0  0
 22 15  1  0  0  0  0
 21 23  1  1  0  0  0
 23 22  1  0  0  0  0
 24 16  1  0  0  0  0
 25 21  1  0  0  0  0
 18 26  1  1  0  0  0
 26 19  2  0  0  0  0
 27 20  2  0  0  0  0
 22 27  1  6  0  0  0
 28 24  2  0  0  0  0
 28 25  1  0  0  0  0
 19 29  1  4  0  0  0
 20 30  1  4  0  0  0
 31 23  2  0  0  0  0
 32 24  1  0  0  0  0
 33 25  2  0  0  0  0
 34  5  1  0  0  0  0
 35  6  1  0  0  0  0
 36  8  1  0  0  0  0
 37 13  1  0  0  0  0
 16 38  1  1  0  0  0
 18 39  1  1  0  0  0
 21 40  1  6  0  0  0
 22 41  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0011224

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H31N3O5/c1-5-6-8-13-19(29)26-18(17-11-9-7-10-12-17)14-20(30)27-22(15(2)3)23(31)21-16(4)24(32)28-25(21)33/h5-13,15-16,18,21-22H,14H2,1-4H3,(H,26,29)(H,27,30)(H,28,32,33)/b6-5+,13-8+/t16-,18-,21+,22-/m0/s1

> <INCHI_KEY>
WMLLJSBRSSYYPT-PQUJRENYSA-N

> <FORMULA>
C25H31N3O5

> <MOLECULAR_WEIGHT>
453.539

> <EXACT_MASS>
453.22637111

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
48.20467800707707

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E)-N-[(1S)-2-{[(2S)-1-[(3R,4S)-5-hydroxy-4-methyl-2-oxo-3,4-dihydro-2H-pyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-C-hydroxycarbonimidoyl}-1-phenylethyl]hexa-2,4-dienimidic acid

> <ALOGPS_LOGP>
3.36

> <JCHEM_LOGP>
4.072096977278334

> <ALOGPS_LOGS>
-5.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.990976148395541

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.233830482964581

> <JCHEM_PKA_STRONGEST_BASIC>
3.5592847759629316

> <JCHEM_POLAR_SURFACE_AREA>
131.91000000000003

> <JCHEM_REFRACTIVITY>
126.78229999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.28e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E)-N-[(1S)-2-{[(2S)-1-[(3R,4S)-5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-C-hydroxycarbonimidoyl}-1-phenylethyl]hexa-2,4-dienimidic 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     -10.869  10.435   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.134  15.825   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.802  15.825   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.512  10.776   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.535  11.205   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.201  10.435   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.867  18.135   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.868  11.205   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.200  17.365   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.533  17.365   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.200  15.825   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.533  15.825   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.868  12.745   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.533  12.745   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.468  15.055   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.048  10.300   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.867  15.055   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.867  13.515   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.534  13.515   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.199  13.515   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.802  11.205   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.468  13.515   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.802  12.745   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.572   8.835   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.556  10.300   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      -4.200  12.745   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0       1.134  12.745   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0       3.032   8.835   0.000  0.00  0.00           N+0
HETATM   29  O   UNK     0      -5.534  15.055   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -0.199  15.055   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       5.136  13.515   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       5.477   7.589   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       1.091  10.776   0.000  0.00  0.00           O+0
HETATM   34  H   UNK     0      -9.535  12.745   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      -8.201   8.895   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.534  10.435   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0      -8.201  13.515   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0       5.289  11.821   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.533  14.285   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.430  11.904   0.000  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.802  14.285   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2   15                                                            
CONECT    3   15                                                            
CONECT    4   16                                                            
CONECT    5    1    6   34                                                  
CONECT    6    5    8   35                                                  
CONECT    7    9   10                                                       
CONECT    8    6   13   36                                                  
CONECT    9    7   11                                                       
CONECT   10    7   12                                                       
CONECT   11    9   17                                                       
CONECT   12   10   17                                                       
CONECT   13    8   19   37                                                  
CONECT   14   18   20                                                       
CONECT   15    2    3   22                                                  
CONECT   16    4   21   24   38                                             
CONECT   17   11   12   18                                                  
CONECT   18   14   17   26   39                                             
CONECT   19   13   26   29                                                  
CONECT   20   14   27   30                                                  
CONECT   21   16   23   25   40                                             
CONECT   22   15   23   27   41                                             
CONECT   23   21   22   31                                                  
CONECT   24   16   28   32                                                  
CONECT   25   21   28   33                                                  
CONECT   26   18   19                                                       
CONECT   27   20   22                                                       
CONECT   28   24   25                                                       
CONECT   29   19                                                            
CONECT   30   20                                                            
CONECT   31   23                                                            
CONECT   32   24                                                            
CONECT   33   25                                                            
CONECT   34    5                                                            
CONECT   35    6                                                            
CONECT   36    8                                                            
CONECT   37   13                                                            
CONECT   38   16                                                            
CONECT   39   18                                                            
CONECT   40   21                                                            
CONECT   41   22                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   84    0
END

Synonyms

Not Available

Molecular Formula

C₂₅H₃₁N₃O₅

Average Mass

453.539

Monoisotopic Mass

453.22637111

IUPAC Name

(2E,4E)-N-[(1S)-2-{[(2S)-1-[(3R,4S)-5-hydroxy-4-methyl-2-oxo-3,4-dihydro-2H-pyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-C-hydroxycarbonimidoyl}-1-phenylethyl]hexa-2,4-dienimidic acid

Traditional Name

(2E,4E)-N-[(1S)-2-{[(2S)-1-[(3R,4S)-5-hydroxy-4-methyl-2-oxo-3,4-dihydropyrrol-3-yl]-3-methyl-1-oxobutan-2-yl]-C-hydroxycarbonimidoyl}-1-phenylethyl]hexa-2,4-dienimidic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C25H31N3O5/c1-5-6-8-13-19(29)26-18(17-11-9-7-10-12-17)14-20(30)27-22(15(2)3)23(31)21-16(4)24(32)28-25(21)33/h5-13,15-16,18,21-22H,14H2,1-4H3,(H,26,29)(H,27,30)(H,28,32,33)/b6-5+,13-8+/t16-,18-,21+,22-/m0/s1

InChI Key

WMLLJSBRSSYYPT-PQUJRENYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Beta amino acids and derivatives

Alternative Parents

Substituents

Beta amino acid or derivatives
Monocyclic benzene moiety
Fatty amide
N-acyl-amine
Pyrrolidone
Fatty acyl
2-pyrrolidone
Benzenoid
1,3-dicarbonyl compound
Carboxylic acid imide
Dicarboximide
Carboxylic acid imide, n-unsubstituted
Pyrrolidine
Lactam
Ketone
Carboxamide group
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0043 g/L	ALOGPS
logP	3.36	ALOGPS
logP	4.07	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.23	ChemAxon
pKa (Strongest Basic)	3.56	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	131.91 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	126.78 m³·mol⁻¹	ChemAxon
Polarizability	48.2 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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 (eluted)	2025-10-23	34.7
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	36.9
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	523.0
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	467.8
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	516.7
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	180.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	2561.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	75.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	326.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	354.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	122.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	156.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	174.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	8.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	172.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	118.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	396.1
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1319.7
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1142.0

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Moiramide B_TMS_1	C/C=C/C=C/C(=N[C@@H](CC(O)=N[C@H](C(=O)[C@@H]1C(=O)N=C(O)[C@H]1C)C(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard non polar	2025-10-23	1567.33
Gas Chromatography	Moiramide B_TMS_2	C/C=C/C=C/C(O)=N[C@@H](CC(=N[C@H](C(=O)[C@@H]1C(=O)N=C(O)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1	standard non polar	2025-10-23	2293.65
Gas Chromatography	Moiramide B_TMS_3	C/C=C/C=C/C(O)=N[C@@H](CC(O)=N[C@H](C(=O)[C@@H]1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)C1=CC=CC=C1	standard non polar	2025-10-23	1686.39
Gas Chromatography	Moiramide B_TMS_4	C/C=C/C=C/C(O)=N[C@@H](CC(O)=N[C@H](C(O[Si](C)(C)C)=C1C(=O)N=C(O)[C@H]1C)C(C)C)C1=CC=CC=C1	standard non polar	2025-10-23	1759.42
Gas Chromatography	Moiramide B_TMS_5	C/C=C/C=C/C(O)=N[C@@H](CC(O)=NC(=C(O[Si](C)(C)C)[C@@H]1C(=O)N=C(O)[C@H]1C)C(C)C)C1=CC=CC=C1	standard non polar	2025-10-23	1638.35
Gas Chromatography	Moiramide B_TMS_6	C/C=C/C=C/C(=N[C@@H](CC(=N[C@H](C(=O)[C@@H]1C(=O)N=C(O)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard non polar	2025-10-23	2286.32
Gas Chromatography	Moiramide B_TMS_7	C/C=C/C=C/C(=N[C@@H](CC(O)=N[C@H](C(=O)[C@@H]1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard non polar	2025-10-23	464.505
Gas Chromatography	Moiramide B_TMS_8	C/C=C/C=C/C(=N[C@@H](CC(O)=N[C@H](C(O[Si](C)(C)C)=C1C(=O)N=C(O)[C@H]1C)C(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard non polar	2025-10-23	2477.15
Gas Chromatography	Moiramide B_TMS_9	C/C=C/C=C/C(=N[C@@H](CC(O)=NC(=C(O[Si](C)(C)C)[C@@H]1C(=O)N=C(O)[C@H]1C)C(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard non polar	2025-10-23	1541.58
Gas Chromatography	Moiramide B_TMS_10	C/C=C/C=C/C(O)=N[C@@H](CC(=N[C@H](C(=O)[C@@H]1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1	standard non polar	2025-10-23	1805.11
Gas Chromatography	Moiramide B_TMS_11	C/C=C/C=C/C(O)=N[C@@H](CC(=N[C@H](C(O[Si](C)(C)C)=C1C(=O)N=C(O)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1	standard non polar	2025-10-23	2693.49
Gas Chromatography	Moiramide B_TMS_12	C/C=C/C=C/C(O)=N[C@@H](CC(=NC(=C(O[Si](C)(C)C)[C@@H]1C(=O)N=C(O)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1	standard non polar	2025-10-23	1440.81
Gas Chromatography	Moiramide B_TMS_13	C/C=C/C=C/C(O)=N[C@@H](CC(O)=N[C@H](C(O[Si](C)(C)C)=C1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)C1=CC=CC=C1	standard non polar	2025-10-23	2543.65
Gas Chromatography	Moiramide B_TMS_14	C/C=C/C=C/C(O)=N[C@@H](CC(O)=NC(=C(O[Si](C)(C)C)[C@@H]1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)C1=CC=CC=C1	standard non polar	2025-10-23	561.551
Gas Chromatography	Moiramide B_TMS_15	C/C=C/C=C/C(=N[C@@H](CC(=N[C@H](C(=O)[C@@H]1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard non polar	2025-10-23	1588.25
Gas Chromatography	Moiramide B_TMS_16	C/C=C/C=C/C(=N[C@@H](CC(=N[C@H](C(O[Si](C)(C)C)=C1C(=O)N=C(O)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard non polar	2025-10-23	555.976
Gas Chromatography	Moiramide B_TMS_17	C/C=C/C=C/C(=N[C@@H](CC(=NC(=C(O[Si](C)(C)C)[C@@H]1C(=O)N=C(O)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard non polar	2025-10-23	2009.54
Gas Chromatography	Moiramide B_TMS_18	C/C=C/C=C/C(=N[C@@H](CC(O)=N[C@H](C(O[Si](C)(C)C)=C1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard non polar	2025-10-23	2474.38
Gas Chromatography	Moiramide B_TMS_19	C/C=C/C=C/C(=N[C@@H](CC(O)=NC(=C(O[Si](C)(C)C)[C@@H]1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard non polar	2025-10-23	1021.39
Gas Chromatography	Moiramide B_TMS_20	C/C=C/C=C/C(O)=N[C@@H](CC(=N[C@H](C(O[Si](C)(C)C)=C1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1	standard non polar	2025-10-23	2478.29
Gas Chromatography	Moiramide B_TMS_21	C/C=C/C=C/C(O)=N[C@@H](CC(=NC(=C(O[Si](C)(C)C)[C@@H]1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1	standard non polar	2025-10-23	1883.35
Gas Chromatography	Moiramide B_TMS_22	C/C=C/C=C/C(=N[C@@H](CC(=N[C@H](C(O[Si](C)(C)C)=C1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard non polar	2025-10-23	1218.84
Gas Chromatography	Moiramide B_TMS_23	C/C=C/C=C/C(=N[C@@H](CC(=NC(=C(O[Si](C)(C)C)[C@@H]1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard non polar	2025-10-23	2343.04
Gas Chromatography	Moiramide B_TMS_1	C/C=C/C=C/C(=N[C@@H](CC(O)=N[C@H](C(=O)[C@@H]1C(=O)N=C(O)[C@H]1C)C(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard polar	2025-10-23	2793.93
Gas Chromatography	Moiramide B_TMS_2	C/C=C/C=C/C(O)=N[C@@H](CC(=N[C@H](C(=O)[C@@H]1C(=O)N=C(O)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1	standard polar	2025-10-23	1644.51
Gas Chromatography	Moiramide B_TMS_3	C/C=C/C=C/C(O)=N[C@@H](CC(O)=N[C@H](C(=O)[C@@H]1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)C1=CC=CC=C1	standard polar	2025-10-23	2595.2
Gas Chromatography	Moiramide B_TMS_4	C/C=C/C=C/C(O)=N[C@@H](CC(O)=N[C@H](C(O[Si](C)(C)C)=C1C(=O)N=C(O)[C@H]1C)C(C)C)C1=CC=CC=C1	standard polar	2025-10-23	2399.72
Gas Chromatography	Moiramide B_TMS_5	C/C=C/C=C/C(O)=N[C@@H](CC(O)=NC(=C(O[Si](C)(C)C)[C@@H]1C(=O)N=C(O)[C@H]1C)C(C)C)C1=CC=CC=C1	standard polar	2025-10-23	1824.66
Gas Chromatography	Moiramide B_TMS_6	C/C=C/C=C/C(=N[C@@H](CC(=N[C@H](C(=O)[C@@H]1C(=O)N=C(O)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard polar	2025-10-23	2861.09
Gas Chromatography	Moiramide B_TMS_7	C/C=C/C=C/C(=N[C@@H](CC(O)=N[C@H](C(=O)[C@@H]1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard polar	2025-10-23	2496.53
Gas Chromatography	Moiramide B_TMS_8	C/C=C/C=C/C(=N[C@@H](CC(O)=N[C@H](C(O[Si](C)(C)C)=C1C(=O)N=C(O)[C@H]1C)C(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard polar	2025-10-23	2072.17
Gas Chromatography	Moiramide B_TMS_9	C/C=C/C=C/C(=N[C@@H](CC(O)=NC(=C(O[Si](C)(C)C)[C@@H]1C(=O)N=C(O)[C@H]1C)C(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard polar	2025-10-23	1524.39
Gas Chromatography	Moiramide B_TMS_10	C/C=C/C=C/C(O)=N[C@@H](CC(=N[C@H](C(=O)[C@@H]1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1	standard polar	2025-10-23	2171.59
Gas Chromatography	Moiramide B_TMS_11	C/C=C/C=C/C(O)=N[C@@H](CC(=N[C@H](C(O[Si](C)(C)C)=C1C(=O)N=C(O)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1	standard polar	2025-10-23	2603.79
Gas Chromatography	Moiramide B_TMS_12	C/C=C/C=C/C(O)=N[C@@H](CC(=NC(=C(O[Si](C)(C)C)[C@@H]1C(=O)N=C(O)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1	standard polar	2025-10-23	2081.06
Gas Chromatography	Moiramide B_TMS_13	C/C=C/C=C/C(O)=N[C@@H](CC(O)=N[C@H](C(O[Si](C)(C)C)=C1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)C1=CC=CC=C1	standard polar	2025-10-23	1251.72
Gas Chromatography	Moiramide B_TMS_14	C/C=C/C=C/C(O)=N[C@@H](CC(O)=NC(=C(O[Si](C)(C)C)[C@@H]1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)C1=CC=CC=C1	standard polar	2025-10-23	3754.92
Gas Chromatography	Moiramide B_TMS_15	C/C=C/C=C/C(=N[C@@H](CC(=N[C@H](C(=O)[C@@H]1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard polar	2025-10-23	2514.47
Gas Chromatography	Moiramide B_TMS_16	C/C=C/C=C/C(=N[C@@H](CC(=N[C@H](C(O[Si](C)(C)C)=C1C(=O)N=C(O)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard polar	2025-10-23	2256.16
Gas Chromatography	Moiramide B_TMS_17	C/C=C/C=C/C(=N[C@@H](CC(=NC(=C(O[Si](C)(C)C)[C@@H]1C(=O)N=C(O)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard polar	2025-10-23	2501.97
Gas Chromatography	Moiramide B_TMS_18	C/C=C/C=C/C(=N[C@@H](CC(O)=N[C@H](C(O[Si](C)(C)C)=C1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard polar	2025-10-23	3012.74
Gas Chromatography	Moiramide B_TMS_19	C/C=C/C=C/C(=N[C@@H](CC(O)=NC(=C(O[Si](C)(C)C)[C@@H]1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard polar	2025-10-23	1435.64
Gas Chromatography	Moiramide B_TMS_20	C/C=C/C=C/C(O)=N[C@@H](CC(=N[C@H](C(O[Si](C)(C)C)=C1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1	standard polar	2025-10-23	2090.73
Gas Chromatography	Moiramide B_TMS_21	C/C=C/C=C/C(O)=N[C@@H](CC(=NC(=C(O[Si](C)(C)C)[C@@H]1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1	standard polar	2025-10-23	1995.37
Gas Chromatography	Moiramide B_TMS_22	C/C=C/C=C/C(=N[C@@H](CC(=N[C@H](C(O[Si](C)(C)C)=C1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard polar	2025-10-23	125.428
Gas Chromatography	Moiramide B_TMS_23	C/C=C/C=C/C(=N[C@@H](CC(=NC(=C(O[Si](C)(C)C)[C@@H]1C(=O)N=C(O[Si](C)(C)C)[C@H]1C)C(C)C)O[Si](C)(C)C)C1=CC=CC=C1)O[Si](C)(C)C	standard polar	2025-10-23	4013.85

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/Eubacteria	Proteobacteria	1	Human ; Human subgingival plaque	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

9919348

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11744644

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

WMLLJSBRSSYYPT-UHFFFAOYSA-N

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 Moiramide B (MMDBc0011224)

MOL for #<Metabolite:0x00007fc954781520>

3D MOL for #<Metabolite:0x00007fc954781520>

3D SDF for #<Metabolite:0x00007fc954781520>

3D-SDF for #<Metabolite:0x00007fc954781520>

PDB for #<Metabolite:0x00007fc954781520>

3D PDB for #<Metabolite:0x00007fc954781520>

SMILES for #<Metabolite:0x00007fc954781520>

INCHI for #<Metabolite:0x00007fc954781520>

Structure for #<Metabolite:0x00007fc954781520>

3D Structure for #<Metabolite:0x00007fc954781520>