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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:02:11 UTC

Update Date

2021-09-26 23:05:47 UTC

HMDB ID

HMDB0252896

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-(gamma-Maleimidobutyryloxy)succinimide

Description

N-(gamma-Maleimidobutyryloxy)succinimide belongs to the class of organic compounds known as maleimides. Maleimides are compounds containing a 2,5-pyrroledione moiety. Based on a literature review a significant number of articles have been published on N-(gamma-Maleimidobutyryloxy)succinimide. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-(gamma-maleimidobutyryloxy)succinimide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-(gamma-Maleimidobutyryloxy)succinimide 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0252896
     RDKit          3D
N-(gamma-Maleimidobutyryloxy)succinimide
 32 33  0  0  0  0  0  0  0  0999 V2000
    0.9922    0.2020    0.8708 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0608   -0.0365   -0.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2186   -0.1903   -1.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4029   -0.0251   -0.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6536   -0.1958   -1.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8413   -0.0453   -0.2317 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5223   -1.0824    0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2221   -2.3062    0.4876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6799   -0.5219    1.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6968    0.7845    0.9289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5833    1.1429    0.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2822    2.2834   -0.3780 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2950   -0.1388   -0.9364 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4971   -0.0035   -0.2842 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6588   -0.7449   -0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6891   -1.6900   -1.5060 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8073   -0.1560    0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1506    0.3643    1.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8294    0.8127    0.8243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0917    1.7415    1.2781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3027    0.5500   -1.9330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913   -1.2188   -1.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4418   -0.7521    0.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4100    1.0366    0.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7247    0.5537   -1.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7059   -1.2329   -1.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3929   -1.0392    1.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4479    1.4538    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5489   -0.9320    0.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2503    0.6564   -0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7601    1.2082    1.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0887   -0.4786    2.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 11  6  1  0
 19 14  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  9 27  1  0
 10 28  1  0
 17 29  1  0
 17 30  1  0
 18 31  1  0
 18 32  1  0
M  END

  Mrv1652309112113022D          

 20 21  0  0  0  0            999 V2000
    1.5557   -4.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1432   -3.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6952   -3.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5237   -2.2218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4489   -3.3644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3627   -4.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9758   -4.7369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1634   -2.9519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8779   -3.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8779   -4.1894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5923   -2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3068   -3.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0213   -2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7357   -3.3644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4894   -3.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6609   -2.2218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0414   -3.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6289   -4.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8220   -4.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2089   -4.7369    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0252896

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C(CCCN1C(=O)C=CC1=O)ON1C(=O)CCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H12N2O6/c15-8-3-4-9(16)13(8)7-1-2-12(19)20-14-10(17)5-6-11(14)18/h3-4H,1-2,5-7H2

> <INCHI_KEY>
PVGATNRYUYNBHO-UHFFFAOYSA-N

> <FORMULA>
C12H12N2O6

> <MOLECULAR_WEIGHT>
280.236

> <EXACT_MASS>
280.069536114

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.764054270525396

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,5-dioxopyrrolidin-1-yl 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoate

> <ALOGPS_LOGP>
0.03

> <JCHEM_LOGP>
-1.0389842210000002

> <ALOGPS_LOGS>
-2.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.709116374805355

> <JCHEM_PKA_STRONGEST_BASIC>
-4.0240144843993715

> <JCHEM_POLAR_SURFACE_AREA>
101.06

> <JCHEM_REFRACTIVITY>
64.34090000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5-dioxopyrrolidin-1-yl 4-(2,5-dioxopyrrol-1-yl)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0252896
     RDKit          3D
N-(gamma-Maleimidobutyryloxy)succinimide
 32 33  0  0  0  0  0  0  0  0999 V2000
    0.9922    0.2020    0.8708 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0608   -0.0365   -0.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2186   -0.1903   -1.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4029   -0.0251   -0.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6536   -0.1958   -1.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8413   -0.0453   -0.2317 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5223   -1.0824    0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2221   -2.3062    0.4876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6799   -0.5219    1.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6968    0.7845    0.9289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5833    1.1429    0.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2822    2.2834   -0.3780 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2950   -0.1388   -0.9364 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4971   -0.0035   -0.2842 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6588   -0.7449   -0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6891   -1.6900   -1.5060 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8073   -0.1560    0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1506    0.3643    1.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8294    0.8127    0.8243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0917    1.7415    1.2781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3027    0.5500   -1.9330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913   -1.2188   -1.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4418   -0.7521    0.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4100    1.0366    0.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7247    0.5537   -1.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7059   -1.2329   -1.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3929   -1.0392    1.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4479    1.4538    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5489   -0.9320    0.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2503    0.6564   -0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7601    1.2082    1.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0887   -0.4786    2.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 11  6  1  0
 19 14  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  9 27  1  0
 10 28  1  0
 17 29  1  0
 17 30  1  0
 18 31  1  0
 18 32  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       2.904  -8.132   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.134  -6.798   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.164  -5.654   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.844  -4.147   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       4.571  -6.280   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.410  -7.812   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.555  -8.842   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       5.905  -5.510   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.239  -6.280   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.239  -7.820   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.572  -5.510   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.906  -6.280   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.240  -5.510   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      12.573  -6.280   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      13.980  -5.654   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.300  -4.147   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      15.011  -6.798   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.241  -8.132   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.734  -7.812   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.590  -8.842   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0252896
HETATM    1  O1  UNL     1       0.992   0.202   0.871  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.061  -0.037  -0.362  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.219  -0.190  -1.108  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.403  -0.025  -0.213  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.654  -0.196  -1.050  1.00  0.00           C  
HETATM    6  N1  UNL     1      -3.841  -0.045  -0.232  1.00  0.00           N  
HETATM    7  C5  UNL     1      -4.522  -1.082   0.460  1.00  0.00           C  
HETATM    8  O2  UNL     1      -4.222  -2.306   0.488  1.00  0.00           O  
HETATM    9  C6  UNL     1      -5.680  -0.522   1.175  1.00  0.00           C  
HETATM   10  C7  UNL     1      -5.697   0.784   0.929  1.00  0.00           C  
HETATM   11  C8  UNL     1      -4.583   1.143   0.063  1.00  0.00           C  
HETATM   12  O3  UNL     1      -4.282   2.283  -0.378  1.00  0.00           O  
HETATM   13  O4  UNL     1       2.295  -0.139  -0.936  1.00  0.00           O  
HETATM   14  N2  UNL     1       3.497  -0.003  -0.284  1.00  0.00           N  
HETATM   15  C9  UNL     1       4.659  -0.745  -0.694  1.00  0.00           C  
HETATM   16  O5  UNL     1       4.689  -1.690  -1.506  1.00  0.00           O  
HETATM   17  C10 UNL     1       5.807  -0.156   0.044  1.00  0.00           C  
HETATM   18  C11 UNL     1       5.151   0.364   1.304  1.00  0.00           C  
HETATM   19  C12 UNL     1       3.829   0.813   0.824  1.00  0.00           C  
HETATM   20  O6  UNL     1       3.092   1.742   1.278  1.00  0.00           O  
HETATM   21  H1  UNL     1      -0.303   0.550  -1.933  1.00  0.00           H  
HETATM   22  H2  UNL     1      -0.191  -1.219  -1.554  1.00  0.00           H  
HETATM   23  H3  UNL     1      -1.442  -0.752   0.601  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.410   1.037   0.136  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.725   0.554  -1.869  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.706  -1.233  -1.485  1.00  0.00           H  
HETATM   27  H7  UNL     1      -6.393  -1.039   1.787  1.00  0.00           H  
HETATM   28  H8  UNL     1      -6.448   1.454   1.333  1.00  0.00           H  
HETATM   29  H9  UNL     1       6.549  -0.932   0.313  1.00  0.00           H  
HETATM   30  H10 UNL     1       6.250   0.656  -0.570  1.00  0.00           H  
HETATM   31  H11 UNL     1       5.760   1.208   1.685  1.00  0.00           H  
HETATM   32  H12 UNL     1       5.089  -0.479   2.017  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4   21   22
CONECT    4    5   23   24
CONECT    5    6   25   26
CONECT    6    7   11
CONECT    7    8    8    9
CONECT    9   10   10   27
CONECT   10   11   28
CONECT   11   12   12
CONECT   13   14
CONECT   14   15   19
CONECT   15   16   16   17
CONECT   17   18   29   30
CONECT   18   19   31   32
CONECT   19   20   20
END

HMDB0252896
     RDKit          3D
N-(gamma-Maleimidobutyryloxy)succinimide
 32 33  0  0  0  0  0  0  0  0999 V2000
    0.9922    0.2020    0.8708 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0608   -0.0365   -0.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2186   -0.1903   -1.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4029   -0.0251   -0.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6536   -0.1958   -1.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8413   -0.0453   -0.2317 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5223   -1.0824    0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2221   -2.3062    0.4876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6799   -0.5219    1.1754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6968    0.7845    0.9289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5833    1.1429    0.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2822    2.2834   -0.3780 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2950   -0.1388   -0.9364 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4971   -0.0035   -0.2842 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6588   -0.7449   -0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6891   -1.6900   -1.5060 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8073   -0.1560    0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1506    0.3643    1.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8294    0.8127    0.8243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0917    1.7415    1.2781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3027    0.5500   -1.9330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913   -1.2188   -1.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4418   -0.7521    0.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4100    1.0366    0.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7247    0.5537   -1.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7059   -1.2329   -1.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3929   -1.0392    1.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4479    1.4538    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5489   -0.9320    0.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2503    0.6564   -0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7601    1.2082    1.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0887   -0.4786    2.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 11  6  1  0
 19 14  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  9 27  1  0
 10 28  1  0
 17 29  1  0
 17 30  1  0
 18 31  1  0
 18 32  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
N-(g-Maleimidobutyryloxy)succinimide	Generator
N-(Γ-maleimidobutyryloxy)succinimide	Generator

Chemical Formula

C₁₂H₁₂N₂O₆

Average Molecular Weight

280.236

Monoisotopic Molecular Weight

280.069536114

IUPAC Name

2,5-dioxopyrrolidin-1-yl 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)butanoate

Traditional Name

2,5-dioxopyrrolidin-1-yl 4-(2,5-dioxopyrrol-1-yl)butanoate

CAS Registry Number

Not Available

SMILES

O=C(CCCN1C(=O)C=CC1=O)ON1C(=O)CCC1=O

InChI Identifier

InChI=1S/C12H12N2O6/c15-8-3-4-9(16)13(8)7-1-2-12(19)20-14-10(17)5-6-11(14)18/h3-4H,1-2,5-7H2

InChI Key

PVGATNRYUYNBHO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as maleimides. Maleimides are compounds containing a 2,5-pyrroledione moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolidines

Sub Class

Pyrrolidones

Direct Parent

Maleimides

Alternative Parents

Substituents

Maleimide
Carboxylic acid imide, n-substituted
2-pyrrolidone
Carboxylic acid imide
Dicarboximide
Pyrroline
Carboxylic acid salt
Lactam
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organic salt
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.03	ALOGPS
logP	-1	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	17.71	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	101.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	64.34 m³·mol⁻¹	ChemAxon
Polarizability	25.76 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	157.831	30932474
DeepCCS	[M-H]-	155.473	30932474
DeepCCS	[M-2H]-	188.358	30932474
DeepCCS	[M+Na]+	163.924	30932474
AllCCS	[M+H]+	161.5	32859911
AllCCS	[M+H-H2O]+	158.0	32859911
AllCCS	[M+NH4]+	164.7	32859911
AllCCS	[M+Na]+	165.7	32859911
AllCCS	[M-H]-	161.4	32859911
AllCCS	[M+Na-2H]-	161.1	32859911
AllCCS	[M+HCOO]-	160.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-(gamma-Maleimidobutyryloxy)succinimide	O=C(CCCN1C(=O)C=CC1=O)ON1C(=O)CCC1=O	3860.7	Standard polar	33892256
N-(gamma-Maleimidobutyryloxy)succinimide	O=C(CCCN1C(=O)C=CC1=O)ON1C(=O)CCC1=O	2519.0	Standard non polar	33892256
N-(gamma-Maleimidobutyryloxy)succinimide	O=C(CCCN1C(=O)C=CC1=O)ON1C(=O)CCC1=O	2472.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-(gamma-Maleimidobutyryloxy)succinimide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0403-6900000000-231837c4d863b8b6fa6c	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(gamma-Maleimidobutyryloxy)succinimide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(gamma-Maleimidobutyryloxy)succinimide 10V, Positive-QTOF	splash10-001i-0090000000-1cc14e8c9de2fb503558	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(gamma-Maleimidobutyryloxy)succinimide 20V, Positive-QTOF	splash10-03e9-2960000000-38ee7b2e5a8ee13d697f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(gamma-Maleimidobutyryloxy)succinimide 40V, Positive-QTOF	splash10-00p3-9540000000-94964174bca3e75b0b5e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(gamma-Maleimidobutyryloxy)succinimide 10V, Negative-QTOF	splash10-0002-9430000000-843b510f8b59c056930b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(gamma-Maleimidobutyryloxy)succinimide 20V, Negative-QTOF	splash10-01ot-8950000000-ed958d353071827d67ae	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(gamma-Maleimidobutyryloxy)succinimide 40V, Negative-QTOF	splash10-0002-9200000000-d76263511f4fab64ad46	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

117712

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

133440

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]

Showing metabocard for N-(gamma-Maleimidobutyryloxy)succinimide (HMDB0252896)

MOL for HMDB0252896 (N-(gamma-Maleimidobutyryloxy)succinimide)

3D MOL for HMDB0252896 (N-(gamma-Maleimidobutyryloxy)succinimide)

3D SDF for HMDB0252896 (N-(gamma-Maleimidobutyryloxy)succinimide)

3D-SDF for HMDB0252896 (N-(gamma-Maleimidobutyryloxy)succinimide)

PDB for HMDB0252896 (N-(gamma-Maleimidobutyryloxy)succinimide)

3D PDB for HMDB0252896 (N-(gamma-Maleimidobutyryloxy)succinimide)

SMILES for HMDB0252896 (N-(gamma-Maleimidobutyryloxy)succinimide)

INCHI for HMDB0252896 (N-(gamma-Maleimidobutyryloxy)succinimide)

Structure for HMDB0252896 (N-(gamma-Maleimidobutyryloxy)succinimide)

3D Structure for HMDB0252896 (N-(gamma-Maleimidobutyryloxy)succinimide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra