MiMeDB: Showing metabocard for Promysalin (MMDBc0024533)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 14:20:05 UTC

Update Date

2025-10-07 16:07:27 UTC

Metabolite ID

MMDBc0024533

Metabolite Identification

Common Name

Promysalin

Description

Promysalin is a secondary metabolite classified as an amphipathic antibiotic, isolated from Pseudomonas putida and Pseudomonas promysalinigenes. Its chemical structure is characterized by a unique combination of salicylic acid, proline, and myristic acid, which are assembled through a proposed hybrid non-ribosomal peptide synthetase-polyketide synthase (NRPS-PKS) biosynthetic pathway (PMID:37567320 ). Promysalin exhibits potent species-specific inhibition of the pathogen Pseudomonas, primarily through the inactivation of succinate dehydrogenase, a critical enzyme in the tricarboxylic acid cycle (PMID:37567320 ). The structure-activity relationship studies have revealed a novel binding site for promysalin on succinate dehydrogenase, which facilitates π-π stacking interactions with a nearby tryptophan residue, suggesting a mechanism for its inhibitory action (PMID:40126084 ). Additionally, promysalin has been shown to work synergistically with vancomycin and antagonistically with aminoglycosides, indicating its potential utility in combination therapies, although these interactions do not reduce minimum inhibitory concentrations (PMID:37938982 ). These findings highlight the intricate chemical interactions and biological pathways involving promysalin, underscoring its significance in antimicrobial research (PMID:40126084 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152116202D          

 37 38  0  0  1  0            999 V2000
   -2.9214    6.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1195    5.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5251    4.9737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232    4.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0510    3.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1287    3.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7416    3.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2492    4.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5421    0.1817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5694   -0.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8259   -0.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3269    2.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9398    2.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8143    0.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3900   -0.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8690   -1.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0418    4.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6267   -0.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7324    2.2280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1139    0.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9214    0.3975    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1412   -0.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2400    5.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0326    5.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3862    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232    1.1983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2307    6.3466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6858    0.0870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4408   -1.1261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6455    5.8890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6271    4.9737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3588    1.3475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3177    1.7703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9306    1.4271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5343    3.0288    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1179    0.5845    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8344    4.7449    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  5  1  0  0  0  0
 10  9  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 14  9  1  0  0  0  0
 15 11  1  0  0  0  0
 16 10  1  0  0  0  0
 17  8  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  2  0  0  0  0
 21 15  1  0  0  0  0
 22 16  2  0  0  0  0
 22 20  1  0  0  0  0
 23 17  1  0  0  0  0
 24 23  1  0  0  0  0
 25 20  1  0  0  0  0
 21 26  1  6  0  0  0
 27 24  2  0  0  0  0
 28 18  1  0  0  0  0
 28 21  1  0  0  0  0
 28 25  1  0  0  0  0
 29 22  1  0  0  0  0
 30 23  1  0  0  0  0
 31 24  1  0  0  0  0
 32 25  2  0  0  0  0
 33 26  2  0  0  0  0
 34 19  1  0  0  0  0
 34 26  1  0  0  0  0
 35 19  1  0  0  0  0
 21 36  1  1  0  0  0
 37 23  1  0  0  0  0
M  END


  Mrv1652305152116202D          

 37 38  0  0  1  0            999 V2000
   -2.9214    6.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1195    5.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5251    4.9737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232    4.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0510    3.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1287    3.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7416    3.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2492    4.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5421    0.1817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5694   -0.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8259   -0.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3269    2.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9398    2.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8143    0.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3900   -0.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8690   -1.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0418    4.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6267   -0.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7324    2.2280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1139    0.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9214    0.3975    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1412   -0.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2400    5.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0326    5.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3862    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232    1.1983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2307    6.3466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6858    0.0870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4408   -1.1261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6455    5.8890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6271    4.9737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3588    1.3475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3177    1.7703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9306    1.4271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5343    3.0288    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1179    0.5845    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8344    4.7449    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  5  1  0  0  0  0
 10  9  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 14  9  1  0  0  0  0
 15 11  1  0  0  0  0
 16 10  1  0  0  0  0
 17  8  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  2  0  0  0  0
 21 15  1  0  0  0  0
 22 16  2  0  0  0  0
 22 20  1  0  0  0  0
 23 17  1  0  0  0  0
 24 23  1  0  0  0  0
 25 20  1  0  0  0  0
 21 26  1  6  0  0  0
 27 24  2  0  0  0  0
 28 18  1  0  0  0  0
 28 21  1  0  0  0  0
 28 25  1  0  0  0  0
 29 22  1  0  0  0  0
 30 23  1  0  0  0  0
 31 24  1  0  0  0  0
 32 25  2  0  0  0  0
 33 26  2  0  0  0  0
 34 19  1  0  0  0  0
 34 26  1  0  0  0  0
 35 19  1  0  0  0  0
 21 36  1  1  0  0  0
 37 23  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0024533

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(CCCCCC)(CCCCCC([H])(O)C(O)=N)OC(=O)[C@]1([H])CCCN1C(=O)C1=CC=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H40N2O6/c1-2-3-4-6-12-19(13-7-5-8-17-23(30)24(27)31)34-26(33)21-15-11-18-28(21)25(32)20-14-9-10-16-22(20)29/h9-10,14,16,19,21,23,29-30H,2-8,11-13,15,17-18H2,1H3,(H2,27,31)/t19?,21-,23?/m0/s1

> <INCHI_KEY>
WMHMGPUINRVYES-SWCONJRYSA-N

> <FORMULA>
C26H40N2O6

> <MOLECULAR_WEIGHT>
476.614

> <EXACT_MASS>
476.288637016

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
54.1521633033492

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-8-[(2S)-1-(2-hydroxybenzoyl)pyrrolidine-2-carbonyloxy]tetradecanimidic acid

> <ALOGPS_LOGP>
3.98

> <JCHEM_LOGP>
2.8552683506359813

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.165530172619803

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.6827793599408016

> <JCHEM_PKA_STRONGEST_BASIC>
12.728025495981086

> <JCHEM_POLAR_SURFACE_AREA>
131.15

> <JCHEM_REFRACTIVITY>
140.59150000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-8-[(2S)-1-(2-hydroxybenzoyl)pyrrolidine-2-carbonyloxy]tetradecanimidic 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      -5.453  11.847   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.823  10.352   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.713   9.284   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.083   7.789   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.095   6.508   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.974   6.722   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.384   6.081   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.465   8.003   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -12.212   0.339   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -12.263  -1.200   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.275  -1.743   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.344   5.227   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.754   4.586   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -10.853   1.065   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.461  -0.436   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -10.955  -2.014   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.945   8.430   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.770  -1.374   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.234   4.159   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -9.546   0.251   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.453   0.742   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -9.597  -1.288   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.315   9.925   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.794  10.352   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -8.188   0.976   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.083   2.237   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       4.164  11.847   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0      -6.880   0.162   0.000  0.00  0.00           N+0
HETATM   29  O   UNK     0      -8.290  -2.102   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.205  10.993   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       4.904   9.284   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -8.137   2.515   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -6.193   3.305   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -3.604   2.664   0.000  0.00  0.00           O+0
HETATM   35  H   UNK     0      -2.864   5.654   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.953   1.091   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.424   8.857   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    6                                                       
CONECT    5    7    8                                                       
CONECT    6    4   12                                                       
CONECT    7    5   13                                                       
CONECT    8    5   17                                                       
CONECT    9   10   14                                                       
CONECT   10    9   16                                                       
CONECT   11   15   18                                                       
CONECT   12    6   19                                                       
CONECT   13    7   19                                                       
CONECT   14    9   20                                                       
CONECT   15   11   21                                                       
CONECT   16   10   22                                                       
CONECT   17    8   23                                                       
CONECT   18   11   28                                                       
CONECT   19   12   13   34   35                                             
CONECT   20   14   22   25                                                  
CONECT   21   15   26   28   36                                             
CONECT   22   16   20   29                                                  
CONECT   23   17   24   30   37                                             
CONECT   24   23   27   31                                                  
CONECT   25   20   28   32                                                  
CONECT   26   21   33   34                                                  
CONECT   27   24                                                            
CONECT   28   18   21   25                                                  
CONECT   29   22                                                            
CONECT   30   23                                                            
CONECT   31   24                                                            
CONECT   32   25                                                            
CONECT   33   26                                                            
CONECT   34   19   26                                                       
CONECT   35   19                                                            
CONECT   36   21                                                            
CONECT   37   23                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

Synonyms

Not Available

Molecular Formula

C₂₆H₄₀N₂O₆

Average Mass

476.614

Monoisotopic Mass

476.288637016

IUPAC Name

2-hydroxy-8-[(2S)-1-(2-hydroxybenzoyl)pyrrolidine-2-carbonyloxy]tetradecanimidic acid

Traditional Name

2-hydroxy-8-[(2S)-1-(2-hydroxybenzoyl)pyrrolidine-2-carbonyloxy]tetradecanimidic acid

CAS Registry Number

Not Available

SMILES

[H]C(CCCCCC)(CCCCCC([H])(O)C(O)=N)OC(=O)[C@]1([H])CCCN1C(=O)C1=CC=CC=C1O

InChI Identifier

InChI=1S/C26H40N2O6/c1-2-3-4-6-12-19(13-7-5-8-17-23(30)24(27)31)34-26(33)21-15-11-18-28(21)25(32)20-14-9-10-16-22(20)29/h9-10,14,16,19,21,23,29-30H,2-8,11-13,15,17-18H2,1H3,(H2,27,31)/t19?,21-,23?/m0/s1

InChI Key

WMHMGPUINRVYES-SWCONJRYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

Proline or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid ester
Salicylic acid or derivatives
Salicylamide
Benzoic acid or derivatives
Benzamide
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine carboxylic acid
N-acylpyrrolidine
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Tertiary carboxylic acid amide
Pyrrolidine
Secondary alcohol
Carboxylic acid ester
Carboxamide group
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
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	0.016 g/L	ALOGPS
logP	3.98	ALOGPS
logP	2.86	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	-2.7	ChemAxon
pKa (Strongest Basic)	12.73	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	131.15 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	140.59 m³·mol⁻¹	ChemAxon
Polarizability	54.15 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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 (eluted)	2025-10-23	135.2
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	53.4
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	642.9
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	707.4
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	761.8
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	218.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	3230.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	164.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	274.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	523.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	156.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	173.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	235.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	10.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	244.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	540.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	490.5
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1768.2
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1498.1

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Promysalin_TMS_1	CCCCCCC(CCCCCC(O[Si](C)(C)C)C(=N)O)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O	standard non polar	2025-10-23	2552.53
Gas Chromatography	Promysalin_TMS_2	CCCCCCC(CCCCCC(O)C(=N)O[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O	standard non polar	2025-10-23	2385.68
Gas Chromatography	Promysalin_TMS_3	CCCCCCC(CCCCCC(O)C(=N)O)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O[Si](C)(C)C	standard non polar	2025-10-23	1545.05
Gas Chromatography	Promysalin_TMS_4	CCCCCCC(CCCCCC(O)C(O)=N[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O	standard non polar	2025-10-23	1291.45
Gas Chromatography	Promysalin_TMS_5	CCCCCCC(CCCCCC(O[Si](C)(C)C)C(=N)O[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O	standard non polar	2025-10-23	2476.91
Gas Chromatography	Promysalin_TMS_6	CCCCCCC(CCCCCC(O[Si](C)(C)C)C(=N)O)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O[Si](C)(C)C	standard non polar	2025-10-23	1191.33
Gas Chromatography	Promysalin_TMS_7	CCCCCCC(CCCCCC(O[Si](C)(C)C)C(O)=N[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O	standard non polar	2025-10-23	1875.44
Gas Chromatography	Promysalin_TMS_8	CCCCCCC(CCCCCC(O)C(=N)O[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O[Si](C)(C)C	standard non polar	2025-10-23	1765.34
Gas Chromatography	Promysalin_TMS_9	CCCCCCC(CCCCCC(O)C(=N[Si](C)(C)C)O[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O	standard non polar	2025-10-23	1482.0
Gas Chromatography	Promysalin_TMS_10	CCCCCCC(CCCCCC(O)C(O)=N[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O[Si](C)(C)C	standard non polar	2025-10-23	2366.21
Gas Chromatography	Promysalin_TMS_11	CCCCCCC(CCCCCC(O[Si](C)(C)C)C(=N)O[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O[Si](C)(C)C	standard non polar	2025-10-23	3035.09
Gas Chromatography	Promysalin_TMS_12	CCCCCCC(CCCCCC(O[Si](C)(C)C)C(=N[Si](C)(C)C)O[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O	standard non polar	2025-10-23	4228.57
Gas Chromatography	Promysalin_TMS_13	CCCCCCC(CCCCCC(O[Si](C)(C)C)C(O)=N[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O[Si](C)(C)C	standard non polar	2025-10-23	2352.31
Gas Chromatography	Promysalin_TMS_14	CCCCCCC(CCCCCC(O)C(=N[Si](C)(C)C)O[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O[Si](C)(C)C	standard non polar	2025-10-23	3200.95
Gas Chromatography	Promysalin_TMS_15	CCCCCCC(CCCCCC(O[Si](C)(C)C)C(=N[Si](C)(C)C)O[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O[Si](C)(C)C	standard non polar	2025-10-23	1551.13
Gas Chromatography	Promysalin_TMS_1	CCCCCCC(CCCCCC(O[Si](C)(C)C)C(=N)O)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O	standard polar	2025-10-23	1581.79
Gas Chromatography	Promysalin_TMS_2	CCCCCCC(CCCCCC(O)C(=N)O[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O	standard polar	2025-10-23	1301.67
Gas Chromatography	Promysalin_TMS_3	CCCCCCC(CCCCCC(O)C(=N)O)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O[Si](C)(C)C	standard polar	2025-10-23	1862.38
Gas Chromatography	Promysalin_TMS_4	CCCCCCC(CCCCCC(O)C(O)=N[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O	standard polar	2025-10-23	2335.04
Gas Chromatography	Promysalin_TMS_5	CCCCCCC(CCCCCC(O[Si](C)(C)C)C(=N)O[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O	standard polar	2025-10-23	2254.94
Gas Chromatography	Promysalin_TMS_6	CCCCCCC(CCCCCC(O[Si](C)(C)C)C(=N)O)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O[Si](C)(C)C	standard polar	2025-10-23	2687.85
Gas Chromatography	Promysalin_TMS_7	CCCCCCC(CCCCCC(O[Si](C)(C)C)C(O)=N[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O	standard polar	2025-10-23	2760.77
Gas Chromatography	Promysalin_TMS_8	CCCCCCC(CCCCCC(O)C(=N)O[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O[Si](C)(C)C	standard polar	2025-10-23	2983.84
Gas Chromatography	Promysalin_TMS_9	CCCCCCC(CCCCCC(O)C(=N[Si](C)(C)C)O[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O	standard polar	2025-10-23	2115.65
Gas Chromatography	Promysalin_TMS_10	CCCCCCC(CCCCCC(O)C(O)=N[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O[Si](C)(C)C	standard polar	2025-10-23	1500.16
Gas Chromatography	Promysalin_TMS_11	CCCCCCC(CCCCCC(O[Si](C)(C)C)C(=N)O[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O[Si](C)(C)C	standard polar	2025-10-23	2456.88
Gas Chromatography	Promysalin_TMS_12	CCCCCCC(CCCCCC(O[Si](C)(C)C)C(=N[Si](C)(C)C)O[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O	standard polar	2025-10-23	1775.64
Gas Chromatography	Promysalin_TMS_13	CCCCCCC(CCCCCC(O[Si](C)(C)C)C(O)=N[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O[Si](C)(C)C	standard polar	2025-10-23	3074.46
Gas Chromatography	Promysalin_TMS_14	CCCCCCC(CCCCCC(O)C(=N[Si](C)(C)C)O[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O[Si](C)(C)C	standard polar	2025-10-23	2778.2
Gas Chromatography	Promysalin_TMS_15	CCCCCCC(CCCCCC(O[Si](C)(C)C)C(=N[Si](C)(C)C)O[Si](C)(C)C)OC(=O)[C@@H]1CCCN1C(=O)C1=CC=CC=C1O[Si](C)(C)C	standard polar	2025-10-23	2032.84

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	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122380159

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 Promysalin (MMDBc0024533)

MOL for #<Metabolite:0x00007fc940e304c0>

3D MOL for #<Metabolite:0x00007fc940e304c0>

3D SDF for #<Metabolite:0x00007fc940e304c0>

3D-SDF for #<Metabolite:0x00007fc940e304c0>

PDB for #<Metabolite:0x00007fc940e304c0>

3D PDB for #<Metabolite:0x00007fc940e304c0>

SMILES for #<Metabolite:0x00007fc940e304c0>

INCHI for #<Metabolite:0x00007fc940e304c0>

Structure for #<Metabolite:0x00007fc940e304c0>

3D Structure for #<Metabolite:0x00007fc940e304c0>