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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 19:46:58 UTC

Update Date

2021-09-26 23:15:10 UTC

HMDB ID

HMDB0258346

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate

Description

2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate, also known as SMCC or N-(4-carboxycyclohexylmethyl)maleimide N-hydroxysuccinimide ester, 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 small amount of articles have been published on 2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2,5-dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1h-pyrrol-1-yl)methyl)cyclohexanecarboxylate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate 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

HMDB0258346
     RDKit          3D
2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cycl...
 42 44  0  0  0  0  0  0  0  0999 V2000
   -2.7125   -1.6745   -1.3739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0796   -0.7525   -0.7800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8352    0.0923    0.0125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2002   -0.0357    0.1659 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1599    0.2057   -0.8688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8773    0.7092   -1.9937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4553   -0.2476   -0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2862   -0.0139    1.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8781   -0.4226    1.3569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3153   -0.9874    2.3245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6224   -0.6382   -0.9633 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1864   -0.7793    0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6546   -0.8758   -0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0619    0.4582   -0.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0824    1.1578    0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3327    0.4644    0.2720 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4124    0.6043   -0.6865 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3685    1.3136   -1.7150 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5251   -0.2155   -0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1994   -0.8165    0.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8454   -0.4259    1.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2262   -0.8318    2.2849 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8633    1.3755   -0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2427    0.6899   -1.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5722   -1.3168   -0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1143    0.0754    0.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0622   -1.6920    0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2777   -1.3578    0.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6060   -1.5663   -1.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5044    0.3625   -1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3166    2.1735   -0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7013    1.3528    1.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5081   -0.3421   -0.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8668   -1.4986    1.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2188    2.2116   -1.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4987    1.8373    0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0515    0.6009   -2.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1511    1.3436   -1.5111 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
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  9 10  2  0
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M  END

  Mrv1652309112121472D          

 24 26  0  0  0  0            999 V2000
    4.1801    3.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6091    2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    1.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.0527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1331    0.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9177    0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8781   -0.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0531   -0.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7982    0.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0136    0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0380    3.1152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0380    4.7652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1242    5.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5111    6.1377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9312    5.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3437    5.0427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7917    4.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9632    3.6227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258346

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C(ON1C(=O)CCC1=O)C1CCC(CN2C(=O)C=CC2=O)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C16H18N2O6/c19-12-5-6-13(20)17(12)9-10-1-3-11(4-2-10)16(23)24-18-14(21)7-8-15(18)22/h5-6,10-11H,1-4,7-9H2

> <INCHI_KEY>
JJAHTWIKCUJRDK-UHFFFAOYSA-N

> <FORMULA>
C16H18N2O6

> <MOLECULAR_WEIGHT>
334.328

> <EXACT_MASS>
334.116486308

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
32.806224216123155

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,5-dioxopyrrolidin-1-yl 4-[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl]cyclohexane-1-carboxylate

> <ALOGPS_LOGP>
1.00

> <JCHEM_LOGP>
0.29438631100000023

> <ALOGPS_LOGS>
-2.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.70829029900903

> <JCHEM_PKA_STRONGEST_BASIC>
-3.731116440436638

> <JCHEM_POLAR_SURFACE_AREA>
101.06

> <JCHEM_REFRACTIVITY>
80.78679999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.15e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
SMCC

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0258346
     RDKit          3D
2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cycl...
 42 44  0  0  0  0  0  0  0  0999 V2000
   -2.7125   -1.6745   -1.3739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0796   -0.7525   -0.7800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8352    0.0923    0.0125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2002   -0.0357    0.1659 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1599    0.2057   -0.8688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8773    0.7092   -1.9937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4553   -0.2476   -0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2862   -0.0139    1.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8781   -0.4226    1.3569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3153   -0.9874    2.3245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6224   -0.6382   -0.9633 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1864   -0.7793    0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6546   -0.8758   -0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0619    0.4582   -0.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0824    1.1578    0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3327    0.4644    0.2720 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4124    0.6043   -0.6865 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3685    1.3136   -1.7150 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5251   -0.2155   -0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1994   -0.8165    0.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8454   -0.4259    1.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2262   -0.8318    2.2849 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8633    1.3755   -0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2427    0.6899   -1.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5722   -1.3168   -0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2436    0.3912   -0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3366    1.0798    1.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0113   -0.5878    1.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2781   -1.4209   -1.6759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1143    0.0754    0.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0622   -1.6920    0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2777   -1.3578    0.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6060   -1.5663   -1.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5044    0.3625   -1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3166    2.1735   -0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7013    1.3528    1.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5081   -0.3421   -0.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8668   -1.4986    1.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2188    2.2116   -1.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4987    1.8373    0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0515    0.6009   -2.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1511    1.3436   -1.5111 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  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 14 23  1  0
 23 24  1  0
  9  4  1  0
 24 11  1  0
 21 16  1  0
  7 25  1  0
  7 26  1  0
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 20 38  1  0
 23 39  1  0
 23 40  1  0
 24 41  1  0
 24 42  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       7.803   5.815   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.137   6.585   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.470   5.815   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.470   4.275   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.137   3.505   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.803   4.275   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.469   3.505   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       6.469   1.965   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       7.715   1.060   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.180   1.536   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.239  -0.405   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.699  -0.405   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.223   1.060   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.759   1.536   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      11.804   6.585   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.138   5.815   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      11.804   8.125   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0      13.138   8.895   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      13.299  10.427   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      12.154  11.457   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      14.805  10.747   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.575   9.413   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.544   8.269   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      14.865   6.762   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15    3   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0258346
HETATM    1  O1  UNL     1      -2.712  -1.675  -1.374  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.080  -0.752  -0.780  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.835   0.092   0.012  1.00  0.00           O  
HETATM    4  N1  UNL     1      -4.200  -0.036   0.166  1.00  0.00           N  
HETATM    5  C2  UNL     1      -5.160   0.206  -0.869  1.00  0.00           C  
HETATM    6  O3  UNL     1      -4.877   0.709  -1.994  1.00  0.00           O  
HETATM    7  C3  UNL     1      -6.455  -0.248  -0.333  1.00  0.00           C  
HETATM    8  C4  UNL     1      -6.286  -0.014   1.155  1.00  0.00           C  
HETATM    9  C5  UNL     1      -4.878  -0.423   1.357  1.00  0.00           C  
HETATM   10  O4  UNL     1      -4.315  -0.987   2.324  1.00  0.00           O  
HETATM   11  C6  UNL     1      -0.622  -0.638  -0.963  1.00  0.00           C  
HETATM   12  C7  UNL     1       0.186  -0.779   0.284  1.00  0.00           C  
HETATM   13  C8  UNL     1       1.655  -0.876  -0.175  1.00  0.00           C  
HETATM   14  C9  UNL     1       2.062   0.458  -0.668  1.00  0.00           C  
HETATM   15  C10 UNL     1       3.082   1.158   0.154  1.00  0.00           C  
HETATM   16  N2  UNL     1       4.333   0.464   0.272  1.00  0.00           N  
HETATM   17  C11 UNL     1       5.412   0.604  -0.687  1.00  0.00           C  
HETATM   18  O5  UNL     1       5.369   1.314  -1.715  1.00  0.00           O  
HETATM   19  C12 UNL     1       6.525  -0.215  -0.235  1.00  0.00           C  
HETATM   20  C13 UNL     1       6.199  -0.817   0.888  1.00  0.00           C  
HETATM   21  C14 UNL     1       4.845  -0.426   1.246  1.00  0.00           C  
HETATM   22  O6  UNL     1       4.226  -0.832   2.285  1.00  0.00           O  
HETATM   23  C15 UNL     1       0.863   1.375  -0.868  1.00  0.00           C  
HETATM   24  C16 UNL     1      -0.243   0.690  -1.604  1.00  0.00           C  
HETATM   25  H1  UNL     1      -6.572  -1.317  -0.540  1.00  0.00           H  
HETATM   26  H2  UNL     1      -7.244   0.391  -0.767  1.00  0.00           H  
HETATM   27  H3  UNL     1      -6.337   1.080   1.304  1.00  0.00           H  
HETATM   28  H4  UNL     1      -7.011  -0.588   1.764  1.00  0.00           H  
HETATM   29  H5  UNL     1      -0.278  -1.421  -1.676  1.00  0.00           H  
HETATM   30  H6  UNL     1       0.114   0.075   0.962  1.00  0.00           H  
HETATM   31  H7  UNL     1      -0.062  -1.692   0.871  1.00  0.00           H  
HETATM   32  H8  UNL     1       2.278  -1.358   0.567  1.00  0.00           H  
HETATM   33  H9  UNL     1       1.606  -1.566  -1.057  1.00  0.00           H  
HETATM   34  H10 UNL     1       2.504   0.362  -1.714  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.317   2.173  -0.263  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.701   1.353   1.188  1.00  0.00           H  
HETATM   37  H13 UNL     1       7.508  -0.342  -0.725  1.00  0.00           H  
HETATM   38  H14 UNL     1       6.867  -1.499   1.443  1.00  0.00           H  
HETATM   39  H15 UNL     1       1.219   2.212  -1.515  1.00  0.00           H  
HETATM   40  H16 UNL     1       0.499   1.837   0.053  1.00  0.00           H  
HETATM   41  H17 UNL     1      -0.052   0.601  -2.687  1.00  0.00           H  
HETATM   42  H18 UNL     1      -1.151   1.344  -1.511  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4
CONECT    4    5    9
CONECT    5    6    6    7
CONECT    7    8   25   26
CONECT    8    9   27   28
CONECT    9   10   10
CONECT   11   12   24   29
CONECT   12   13   30   31
CONECT   13   14   32   33
CONECT   14   15   23   34
CONECT   15   16   35   36
CONECT   16   17   21
CONECT   17   18   18   19
CONECT   19   20   20   37
CONECT   20   21   38
CONECT   21   22   22
CONECT   23   24   39   40
CONECT   24   41   42
END

HMDB0258346
     RDKit          3D
2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cycl...
 42 44  0  0  0  0  0  0  0  0999 V2000
   -2.7125   -1.6745   -1.3739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0796   -0.7525   -0.7800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8352    0.0923    0.0125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2002   -0.0357    0.1659 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1599    0.2057   -0.8688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8773    0.7092   -1.9937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4553   -0.2476   -0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2862   -0.0139    1.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8781   -0.4226    1.3569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3153   -0.9874    2.3245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6224   -0.6382   -0.9633 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1864   -0.7793    0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6546   -0.8758   -0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0619    0.4582   -0.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0824    1.1578    0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3327    0.4644    0.2720 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4124    0.6043   -0.6865 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3685    1.3136   -1.7150 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5251   -0.2155   -0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1994   -0.8165    0.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8454   -0.4259    1.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2262   -0.8318    2.2849 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8633    1.3755   -0.8677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2427    0.6899   -1.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5722   -1.3168   -0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2436    0.3912   -0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3366    1.0798    1.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0113   -0.5878    1.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2781   -1.4209   -1.6759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1143    0.0754    0.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0622   -1.6920    0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2777   -1.3578    0.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6060   -1.5663   -1.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5044    0.3625   -1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3166    2.1735   -0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7013    1.3528    1.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5081   -0.3421   -0.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8668   -1.4986    1.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2188    2.2116   -1.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4987    1.8373    0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0515    0.6009   -2.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1511    1.3436   -1.5111 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  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 14 23  1  0
 23 24  1  0
  9  4  1  0
 24 11  1  0
 21 16  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 19 37  1  0
 20 38  1  0
 23 39  1  0
 23 40  1  0
 24 41  1  0
 24 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-(4-Carboxycyclohexylmethyl)maleimide N-hydroxysuccinimide ester	ChEBI
N-Hydroxysuccinimidyl 4-(N-maleimidomethylcyclohexane)-1-carboxylate	ChEBI
SMCC	ChEBI
N-Hydroxysuccinimidyl 4-(N-maleimidomethylcyclohexane)-1-carboxylic acid	Generator
2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylic acid	Generator
Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylic acid	HMDB
N-SMC-Carboxylate	HMDB
N-Succinimidyl-4-(N-maleimidomethyl)cyclohexane-1-carboxylic acid	HMDB
SMCC Compound	HMDB

Chemical Formula

C₁₆H₁₈N₂O₆

Average Molecular Weight

334.328

Monoisotopic Molecular Weight

334.116486308

IUPAC Name

2,5-dioxopyrrolidin-1-yl 4-[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl]cyclohexane-1-carboxylate

Traditional Name

SMCC

CAS Registry Number

Not Available

SMILES

O=C(ON1C(=O)CCC1=O)C1CCC(CN2C(=O)C=CC2=O)CC1

InChI Identifier

InChI=1S/C16H18N2O6/c19-12-5-6-13(20)17(12)9-10-1-3-11(4-2-10)16(23)24-18-14(21)7-8-15(18)22/h5-6,10-11H,1-4,7-9H2

InChI Key

JJAHTWIKCUJRDK-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

maleimides (CHEBI:63174 )
N-hydroxysuccinimide ester (CHEBI:63174 )

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	1	ALOGPS
logP	0.29	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	17.71	ChemAxon
pKa (Strongest Basic)	-3.7	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	5	ChemAxon
Refractivity	80.79 m³·mol⁻¹	ChemAxon
Polarizability	32.81 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	175.32	30932474
DeepCCS	[M-H]-	172.962	30932474
DeepCCS	[M-2H]-	206.997	30932474
DeepCCS	[M+Na]+	182.224	30932474
AllCCS	[M+H]+	176.0	32859911
AllCCS	[M+H-H2O]+	173.1	32859911
AllCCS	[M+NH4]+	178.8	32859911
AllCCS	[M+Na]+	179.5	32859911
AllCCS	[M-H]-	176.6	32859911
AllCCS	[M+Na-2H]-	176.4	32859911
AllCCS	[M+HCOO]-	176.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate	O=C(ON1C(=O)CCC1=O)C1CCC(CN2C(=O)C=CC2=O)CC1	4284.3	Standard polar	33892256
2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate	O=C(ON1C(=O)CCC1=O)C1CCC(CN2C(=O)C=CC2=O)CC1	3060.9	Standard non polar	33892256
2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate	O=C(ON1C(=O)CCC1=O)C1CCC(CN2C(=O)C=CC2=O)CC1	2914.4	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 - 2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ox-5940000000-3eeaa184a00eb5cc761f	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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

111419

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate

METLIN ID

Not Available

PubChem Compound

125175

PDB ID

Not Available

ChEBI ID

63174

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 2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate (HMDB0258346)

MOL for HMDB0258346 (2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate)

3D MOL for HMDB0258346 (2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate)

3D SDF for HMDB0258346 (2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate)

3D-SDF for HMDB0258346 (2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate)

PDB for HMDB0258346 (2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate)

3D PDB for HMDB0258346 (2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate)

SMILES for HMDB0258346 (2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate)

INCHI for HMDB0258346 (2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate)

Structure for HMDB0258346 (2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate)

3D Structure for HMDB0258346 (2,5-Dioxopyrrolidin-1-yl 4-((2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)methyl)cyclohexanecarboxylate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra