Showing metabocard for N-ethylmaleimide (MMDBc0054586)

Pharmaceutical
Xenobiotic
Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-05 23:19:25 UTC
Update Date2025-10-07 16:04:13 UTC
Metabolite IDMMDBc0054586
Metabolite Identification
Common NameN-ethylmaleimide
DescriptionN-ethylmaleimide is a member of the chemical class of maleimides, characterized by its reactive maleimide functional group. This compound is known for its ability to irreversibly modify thiol groups in proteins, thereby serving as a thiol-blocking agent in various biochemical assays. In cellular biology, N-ethylmaleimide plays a critical role in the regulation of protein interactions and vesicle trafficking. It is particularly involved in the disassembly of SNARE complexes, which are essential for neurotransmitter release and synaptic plasticity, as evidenced by the action of N-ethylmaleimide sensitive factor (NSF) and soluble NSF attachment proteins (SNAPs) (PMID:40993127 ). Disruption of these complexes by botulinum neurotoxin A (BoNT/A) highlights its significance in neuronal function, impacting processes such as capsaicin-evoked CGRP release (PMID:40956003 ). Furthermore, N-ethylmaleimide is implicated in pathways involving calcium signaling and exocytotic fusion, underscoring its relevance in neurotransmitter receptor trafficking (PMID:40894625 ). Its utility extends to diagnostic applications, particularly in assessing the role of SNAP-25 in major depressive disorder (MDD) (PMID:40840974 ). Overall, N-ethylmaleimide serves as a crucial tool in understanding protein dynamics and cellular signaling pathways.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x0000561537d04f10>


  Mrv0541 02231216352D          

  9  9  0  0  0  0            999 V2000
    2.1913    1.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x0000561537d04f10>

HMDB0255137
     RDKit          3D
N-ethylmaleimide
 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.2361   -0.0924   -0.4891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2199    0.5547    0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1198    0.1532    0.1395 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9226   -0.9132    0.6299 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5243   -1.7491    1.4736 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2543   -0.8768    0.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2617    0.1519   -0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9810    0.8395   -0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6808    1.8604   -1.4709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6004   -1.0702   -0.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8540   -0.2637   -1.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1076    0.5899   -0.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5437    0.3354    1.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3059    1.6487    0.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0167   -1.6036    0.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1066    0.4351   -1.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8  3  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  6 15  1  0
  7 16  1  0
M  END
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3D SDF for #<Metabolite:0x0000561537d04f10>


  Mrv0541 02231216352D          

  9  9  0  0  0  0            999 V2000
    2.1913    1.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054586

> <DATABASE_NAME>
MIME

> <SMILES>
CCN1C(=O)C=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H7NO2/c1-2-7-5(8)3-4-6(7)9/h3-4H,2H2,1H3

> <INCHI_KEY>
HDFGOPSGAURCEO-UHFFFAOYSA-N

> <FORMULA>
C6H7NO2

> <MOLECULAR_WEIGHT>
125.1253

> <EXACT_MASS>
125.047678473

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
11.992895940408747

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-ethyl-2,5-dihydro-1H-pyrrole-2,5-dione

> <ALOGPS_LOGP>
0.02

> <JCHEM_LOGP>
-0.05541890466666666

> <ALOGPS_LOGS>
0.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.316433442691647

> <JCHEM_POLAR_SURFACE_AREA>
37.38

> <JCHEM_REFRACTIVITY>
32.9967

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.54e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-ethylmaleimide

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for #<Metabolite:0x0000561537d04f10>

HMDB0255137
     RDKit          3D
N-ethylmaleimide
 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.2361   -0.0924   -0.4891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2199    0.5547    0.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1198    0.1532    0.1395 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9226   -0.9132    0.6299 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5243   -1.7491    1.4736 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2543   -0.8768    0.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2617    0.1519   -0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9810    0.8395   -0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6808    1.8604   -1.4709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6004   -1.0702   -0.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8540   -0.2637   -1.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1076    0.5899   -0.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5437    0.3354    1.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3059    1.6487    0.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0167   -1.6036    0.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1066    0.4351   -1.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8  3  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  6 15  1  0
  7 16  1  0
M  END
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PDB for #<Metabolite:0x0000561537d04f10>

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       4.090   3.157   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.770   1.651   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.306   1.175   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for #<Metabolite:0x0000561537d04f10>

COMPND    HMDB0255137
HETATM    1  C1  UNL     1      -2.236  -0.092  -0.489  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.220   0.555   0.418  1.00  0.00           C  
HETATM    3  N1  UNL     1       0.120   0.153   0.139  1.00  0.00           N  
HETATM    4  C3  UNL     1       0.923  -0.913   0.630  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.524  -1.749   1.474  1.00  0.00           O  
HETATM    6  C4  UNL     1       2.254  -0.877   0.006  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.262   0.152  -0.817  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.981   0.839  -0.792  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.681   1.860  -1.471  1.00  0.00           O  
HETATM   10  H1  UNL     1      -2.600  -1.070  -0.093  1.00  0.00           H  
HETATM   11  H2  UNL     1      -1.854  -0.264  -1.511  1.00  0.00           H  
HETATM   12  H3  UNL     1      -3.108   0.590  -0.560  1.00  0.00           H  
HETATM   13  H4  UNL     1      -1.544   0.335   1.462  1.00  0.00           H  
HETATM   14  H5  UNL     1      -1.306   1.649   0.287  1.00  0.00           H  
HETATM   15  H6  UNL     1       3.017  -1.604   0.244  1.00  0.00           H  
HETATM   16  H7  UNL     1       3.107   0.435  -1.420  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3   13   14
CONECT    3    4    8
CONECT    4    5    5    6
CONECT    6    7    7   15
CONECT    7    8   16
CONECT    8    9    9
END
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SMILES for #<Metabolite:0x0000561537d04f10>

CCN1C(=O)C=CC1=O
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INCHI for #<Metabolite:0x0000561537d04f10>

InChI=1S/C6H7NO2/c1-2-7-5(8)3-4-6(7)9/h3-4H,2H2,1H3
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Synonyms
ValueSource
EthylmaleimideChEBI
NEMChEBI
N EthylmaleimideMeSH
Molecular FormulaC6H7NO2
Average Mass125.1253
Monoisotopic Mass125.047678473
IUPAC Name1-ethyl-2,5-dihydro-1H-pyrrole-2,5-dione
Traditional NameN-ethylmaleimide
CAS Registry NumberNot Available
SMILES
CCN1C(=O)C=CC1=O
InChI Identifier
InChI=1S/C6H7NO2/c1-2-7-5(8)3-4-6(7)9/h3-4H,2H2,1H3
InChI KeyHDFGOPSGAURCEO-UHFFFAOYSA-N