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Showing metabocard for N-ethylmaleimide (HMDB0255137)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 14:42:33 UTC
Update Date2021-09-26 23:09:43 UTC
HMDB IDHMDB0255137
Secondary Accession NumbersNone
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. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-ethylmaleimide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-ethylmaleimide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0255137 (N-ethylmaleimide)

  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 HMDB0255137 (N-ethylmaleimide)

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 HMDB0255137 (N-ethylmaleimide)

  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>
HMDB0255137

> <DATABASE_NAME>
hmdb

> <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 HMDB0255137 (N-ethylmaleimide)

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 HMDB0255137 (N-ethylmaleimide)

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 HMDB0255137 (N-ethylmaleimide)

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 HMDB0255137 (N-ethylmaleimide)

CCN1C(=O)C=CC1=O
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INCHI for HMDB0255137 (N-ethylmaleimide)

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
Chemical FormulaC6H7NO2
Average Molecular Weight125.1253
Monoisotopic Molecular Weight125.047678473
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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as maleimides. Maleimides are compounds containing a 2,5-pyrroledione moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassPyrrolidones
Direct ParentMaleimides
Alternative Parents
Substituents
  • Maleimide
  • Carboxylic acid imide, n-substituted
  • Carboxylic acid imide
  • Dicarboximide
  • Pyrroline
  • Azacycle
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02967
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC02441
BioCyc IDN-ETHYLMALEIMIDE
BiGG IDNot Available
Wikipedia LinkN-Ethylmaleimide
METLIN IDNot Available
PubChem Compound4362
PDB IDNot Available
ChEBI ID44485
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Transporters

Enzyme Details
1. Multidrug resistance-associated protein 6
General function:
Involved in ATP binding
Specific function:
May participate directly in the active transport of drugs into subcellular organelles or influence drug distribution indirectly. Transports glutathione conjugates as leukotriene-c4 (LTC4) and N-ethylmaleimide S-glutathione (NEM-GS)
Gene Name:
ABCC6
Uniprot ID:
O95255
Molecular weight:
164904.8