Showing metabocard for N-ethylmaleimide (MMDBc0054586)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-06-05 23:19:25 UTC
Update Date2024-04-30 20:54:29 UTC
Metabolite IDMMDBc0054586
Metabolite Identification
Common NameN-ethylmaleimide
DescriptionN-Ethylmaleimide, also known as NEM, belongs to the class of organic compounds known as maleimides. Maleimides are compounds containing a 2,5-pyrroledione moiety. N-Ethylmaleimide (NEM) is an organic compound that is derived from maleic acid. NEM is a Michael Acceptor in Michael Reaction, which means that it adds nucleophiles such as thiols. Reaction with thiols occur in the pH range 6.5–7.5, NEM may react with amines or undergo hydrolysis at a more alkaline pH. NEM has been widely used to probe the functional role of thiol groups in enzymology. N-Ethylmaleimide is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Ethylmaleimide was used by Arthur Kornberg and colleagues to knock out DNA polymerase III in order to compare its activity to that of DNA polymerase I (pol III and I, respectively). This discovery contributed to the molecular identification of K-Cl cotransport (KCC) in human embryonic cells transfected by KCC1 isoform cDNA, 16 years later. In lysis buffers, 20 to 25 mM of NEM is used to inhibit de-sumoylation of proteins for Western Blot analysis. Despite repeated unsuccessful attempts to identify chemically the target thiol group, at physiological pH, NEM may form adducts with thiols within protein kinases that phosphorylate KCC at specific serine and threonine residues primarily within the C-terminal domain of the transporter. The resulting thioether features a strong C-S bond and the reaction is virtually irreversible.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00005634c2b0bad8>


  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:0x00005634c2b0bad8>

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:0x00005634c2b0bad8>


  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:0x00005634c2b0bad8>

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:0x00005634c2b0bad8>

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:0x00005634c2b0bad8>

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:0x00005634c2b0bad8>

CCN1C(=O)C=CC1=O
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INCHI for #<Metabolite:0x00005634c2b0bad8>

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