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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-08-31 18:25:52 UTC

Update Date

2021-09-26 22:48:58 UTC

HMDB ID

HMDB0242493

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate

Description

(2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate, also known as methoxypolyethylene glycol succinimidylsuccinate or SS-PEG, belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. Based on a literature review very few articles have been published on (2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate. This compound has been identified in human blood as reported by (PMID: 31557052 ). (2,5-dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate 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) 5-(2-hydroxyethoxy)-4-oxopentanoate 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

HMDB0242493
     RDKit          3D
(2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate
 34 34  0  0  0  0  0  0  0  0999 V2000
   -1.9995   -1.8831    2.5290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2711   -1.5370    1.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1599   -0.9572    0.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1676   -1.1404    1.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2310   -0.5260    0.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9643    0.0165   -0.6298 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5604   -0.5106    0.8646 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5536    0.0487    0.1047 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6614    0.7553    0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7128    1.1950    1.8297 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7239    0.8684   -0.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8330    0.9999   -1.6341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7299    0.0721   -1.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0491   -0.5951   -2.1352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6248   -1.7284    0.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8688   -1.4448   -0.4256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7236   -0.2186   -0.9539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5551    0.8553   -0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2941    2.0587   -0.9205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0281   -1.3386   -0.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3088    0.1763    0.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3733   -2.1857    1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0831   -0.5459    2.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2807    1.7902   -0.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3442   -0.0415   -0.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3664    0.7405   -2.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4606    2.0477   -1.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9220   -2.8307    1.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3842   -1.2262    1.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365    0.1678   -1.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2318   -0.2704   -1.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6259    0.6122   -0.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2336    0.9950    0.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1274    2.5491   -0.9999 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
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
  2 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 13  8  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 15 28  1  0
 15 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
 18 33  1  0
 19 34  1  0
M  END

  Mrv1652308312120352D          

 19 19  0  0  0  0            999 V2000
   -0.9806    2.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5681    3.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2389    3.0975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8519    3.6496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3251    2.2771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4286    1.9415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6001    1.1345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540    2.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540    3.1021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830    2.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8974    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8974    1.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119    2.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3264    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0409    2.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7553    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4698    2.2771    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  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242493

> <DATABASE_NAME>
hmdb

> <SMILES>
OCCOCC(=O)CCC(=O)ON1C(=O)CCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H15NO7/c13-5-6-18-7-8(14)1-4-11(17)19-12-9(15)2-3-10(12)16/h13H,1-7H2

> <INCHI_KEY>
OVPTZXRXNNJKSJ-UHFFFAOYSA-N

> <FORMULA>
C11H15NO7

> <MOLECULAR_WEIGHT>
273.241

> <EXACT_MASS>
273.084851827

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
26.106393408041782

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,5-dioxopyrrolidin-1-yl 5-(2-hydroxyethoxy)-4-oxopentanoate

> <ALOGPS_LOGP>
-0.64

> <JCHEM_LOGP>
-1.5634956103333337

> <ALOGPS_LOGS>
-1.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.759091564989415

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.00720191103255

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7461925389987885

> <JCHEM_POLAR_SURFACE_AREA>
110.21000000000001

> <JCHEM_REFRACTIVITY>
60.38760000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5-dioxopyrrolidin-1-yl 5-(2-hydroxyethoxy)-4-oxopentanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242493
     RDKit          3D
(2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate
 34 34  0  0  0  0  0  0  0  0999 V2000
   -1.9995   -1.8831    2.5290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2711   -1.5370    1.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1599   -0.9572    0.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1676   -1.1404    1.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2310   -0.5260    0.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9643    0.0165   -0.6298 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5604   -0.5106    0.8646 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5536    0.0487    0.1047 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6614    0.7553    0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7128    1.1950    1.8297 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7239    0.8684   -0.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8330    0.9999   -1.6341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7299    0.0721   -1.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0491   -0.5951   -2.1352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6248   -1.7284    0.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8688   -1.4448   -0.4256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7236   -0.2186   -0.9539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5551    0.8553   -0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2941    2.0587   -0.9205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0281   -1.3386   -0.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3088    0.1763    0.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3733   -2.1857    1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0831   -0.5459    2.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2807    1.7902   -0.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3442   -0.0415   -0.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3664    0.7405   -2.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4606    2.0477   -1.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9220   -2.8307    1.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3842   -1.2262    1.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365    0.1678   -1.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2318   -0.2704   -1.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6259    0.6122   -0.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2336    0.9950    0.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1274    2.5491   -0.9999 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
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
  2 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 13  8  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 15 28  1  0
 15 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
 18 33  1  0
 19 34  1  0
M  END

HEADER    PROTEIN                                 31-AUG-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-AUG-21         0                                  
HETATM    1  C   UNK     0      -1.830   4.769   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.060   6.102   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.446   5.782   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.590   6.813   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       0.607   4.251   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -0.800   3.624   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.120   2.118   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.941   3.481   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.274   4.251   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.274   5.791   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.608   3.481   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.942   4.251   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.275   3.481   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.275   1.941   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.609   4.251   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.943   3.481   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.276   4.251   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.610   3.481   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.944   4.251   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   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0242493
HETATM    1  O1  UNL     1      -2.000  -1.883   2.529  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.271  -1.537   1.362  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.160  -0.957   0.595  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.168  -1.140   1.333  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.231  -0.526   0.487  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.964   0.016  -0.630  1.00  0.00           O  
HETATM    7  O3  UNL     1       2.560  -0.511   0.865  1.00  0.00           O  
HETATM    8  N1  UNL     1       3.554   0.049   0.105  1.00  0.00           N  
HETATM    9  C5  UNL     1       4.661   0.755   0.661  1.00  0.00           C  
HETATM   10  O4  UNL     1       4.713   1.195   1.830  1.00  0.00           O  
HETATM   11  C6  UNL     1       5.724   0.868  -0.392  1.00  0.00           C  
HETATM   12  C7  UNL     1       4.833   1.000  -1.634  1.00  0.00           C  
HETATM   13  C8  UNL     1       3.730   0.072  -1.305  1.00  0.00           C  
HETATM   14  O5  UNL     1       3.049  -0.595  -2.135  1.00  0.00           O  
HETATM   15  C9  UNL     1      -3.625  -1.728   0.858  1.00  0.00           C  
HETATM   16  O6  UNL     1      -3.869  -1.445  -0.426  1.00  0.00           O  
HETATM   17  C10 UNL     1      -3.724  -0.219  -0.954  1.00  0.00           C  
HETATM   18  C11 UNL     1      -4.555   0.855  -0.260  1.00  0.00           C  
HETATM   19  O7  UNL     1      -4.294   2.059  -0.920  1.00  0.00           O  
HETATM   20  H1  UNL     1      -1.028  -1.339  -0.419  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.309   0.176   0.569  1.00  0.00           H  
HETATM   22  H3  UNL     1       0.373  -2.186   1.588  1.00  0.00           H  
HETATM   23  H4  UNL     1       0.083  -0.546   2.274  1.00  0.00           H  
HETATM   24  H5  UNL     1       6.281   1.790  -0.186  1.00  0.00           H  
HETATM   25  H6  UNL     1       6.344  -0.042  -0.435  1.00  0.00           H  
HETATM   26  H7  UNL     1       5.366   0.741  -2.547  1.00  0.00           H  
HETATM   27  H8  UNL     1       4.461   2.048  -1.617  1.00  0.00           H  
HETATM   28  H9  UNL     1      -3.922  -2.831   1.008  1.00  0.00           H  
HETATM   29  H10 UNL     1      -4.384  -1.226   1.543  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.736   0.168  -1.171  1.00  0.00           H  
HETATM   31  H12 UNL     1      -4.232  -0.270  -1.995  1.00  0.00           H  
HETATM   32  H13 UNL     1      -5.626   0.612  -0.372  1.00  0.00           H  
HETATM   33  H14 UNL     1      -4.234   0.995   0.791  1.00  0.00           H  
HETATM   34  H15 UNL     1      -5.127   2.549  -1.000  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   15
CONECT    3    4   20   21
CONECT    4    5   22   23
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   13
CONECT    9   10   10   11
CONECT   11   12   24   25
CONECT   12   13   26   27
CONECT   13   14   14
CONECT   15   16   28   29
CONECT   16   17
CONECT   17   18   30   31
CONECT   18   19   32   33
CONECT   19   34
END

HMDB0242493
     RDKit          3D
(2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate
 34 34  0  0  0  0  0  0  0  0999 V2000
   -1.9995   -1.8831    2.5290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2711   -1.5370    1.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1599   -0.9572    0.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1676   -1.1404    1.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2310   -0.5260    0.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9643    0.0165   -0.6298 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5604   -0.5106    0.8646 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5536    0.0487    0.1047 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6614    0.7553    0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7128    1.1950    1.8297 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7239    0.8684   -0.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8330    0.9999   -1.6341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7299    0.0721   -1.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0491   -0.5951   -2.1352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6248   -1.7284    0.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8688   -1.4448   -0.4256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7236   -0.2186   -0.9539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5551    0.8553   -0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2941    2.0587   -0.9205 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0281   -1.3386   -0.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3088    0.1763    0.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3733   -2.1857    1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0831   -0.5459    2.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2807    1.7902   -0.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3442   -0.0415   -0.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3664    0.7405   -2.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4606    2.0477   -1.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9220   -2.8307    1.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3842   -1.2262    1.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365    0.1678   -1.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2318   -0.2704   -1.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6259    0.6122   -0.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2336    0.9950    0.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1274    2.5491   -0.9999 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
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
  2 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 13  8  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 15 28  1  0
 15 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
 18 33  1  0
 19 34  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoic acid	Generator
2,5-Dioxopyrrolidin-1-yl 5-(2-hydroxyethoxy)-4-oxopentanoic acid	HMDB
Methoxypolyethylene glycol succinimidylsuccinate	HMDB
SS-PEG	HMDB

Chemical Formula

C₁₁H₁₅NO₇

Average Molecular Weight

273.241

Monoisotopic Molecular Weight

273.084851827

IUPAC Name

2,5-dioxopyrrolidin-1-yl 5-(2-hydroxyethoxy)-4-oxopentanoate

Traditional Name

2,5-dioxopyrrolidin-1-yl 5-(2-hydroxyethoxy)-4-oxopentanoate

CAS Registry Number

Not Available

SMILES

OCCOCC(=O)CCC(=O)ON1C(=O)CCC1=O

InChI Identifier

InChI=1S/C11H15NO7/c13-5-6-18-7-8(14)1-4-11(17)19-12-9(15)2-3-10(12)16/h13H,1-7H2

InChI Key

OVPTZXRXNNJKSJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Gamma-keto acids and derivatives

Direct Parent

Gamma-keto acids and derivatives

Alternative Parents

Substituents

Gamma-keto acid
2-pyrrolidone
Pyrrolidone
Monosaccharide
Pyrrolidine
Dicarboximide
Lactam
Ketone
Carboxylic acid salt
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
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	-0.64	ALOGPS
logP	-1.6	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	15.01	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	110.21 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	60.39 m³·mol⁻¹	ChemAxon
Polarizability	26.11 Å³	ChemAxon
Number of Rings	1	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]+	154.405	30932474
DeepCCS	[M-H]-	152.047	30932474
DeepCCS	[M-2H]-	185.37	30932474
DeepCCS	[M+Na]+	160.931	30932474
AllCCS	[M+H]+	157.7	32859911
AllCCS	[M+H-H2O]+	154.5	32859911
AllCCS	[M+NH4]+	160.6	32859911
AllCCS	[M+Na]+	161.5	32859911
AllCCS	[M-H]-	161.3	32859911
AllCCS	[M+Na-2H]-	161.5	32859911
AllCCS	[M+HCOO]-	161.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate	OCCOCC(=O)CCC(=O)ON1C(=O)CCC1=O	3548.2	Standard polar	33892256
(2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate	OCCOCC(=O)CCC(=O)ON1C(=O)CCC1=O	2196.8	Standard non polar	33892256
(2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate	OCCOCC(=O)CCC(=O)ON1C(=O)CCC1=O	2288.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate,2TMS,isomer #1	C[Si](C)(C)OCCOCC(=CCC(=O)ON1C(=O)CCC1=O)O[Si](C)(C)C	2464.6	Semi standard non polar	33892256
(2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate,2TMS,isomer #1	C[Si](C)(C)OCCOCC(=CCC(=O)ON1C(=O)CCC1=O)O[Si](C)(C)C	2366.8	Standard non polar	33892256
(2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate,2TMS,isomer #1	C[Si](C)(C)OCCOCC(=CCC(=O)ON1C(=O)CCC1=O)O[Si](C)(C)C	3274.6	Standard polar	33892256
(2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate,2TMS,isomer #2	C[Si](C)(C)OCCOC=C(CCC(=O)ON1C(=O)CCC1=O)O[Si](C)(C)C	2448.7	Semi standard non polar	33892256
(2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate,2TMS,isomer #2	C[Si](C)(C)OCCOC=C(CCC(=O)ON1C(=O)CCC1=O)O[Si](C)(C)C	2345.9	Standard non polar	33892256
(2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate,2TMS,isomer #2	C[Si](C)(C)OCCOC=C(CCC(=O)ON1C(=O)CCC1=O)O[Si](C)(C)C	3292.7	Standard polar	33892256
(2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCOCC(=CCC(=O)ON1C(=O)CCC1=O)O[Si](C)(C)C(C)(C)C	2914.9	Semi standard non polar	33892256
(2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCOCC(=CCC(=O)ON1C(=O)CCC1=O)O[Si](C)(C)C(C)(C)C	2753.4	Standard non polar	33892256
(2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCOCC(=CCC(=O)ON1C(=O)CCC1=O)O[Si](C)(C)C(C)(C)C	3282.2	Standard polar	33892256
(2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCCOC=C(CCC(=O)ON1C(=O)CCC1=O)O[Si](C)(C)C(C)(C)C	2893.2	Semi standard non polar	33892256
(2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCCOC=C(CCC(=O)ON1C(=O)CCC1=O)O[Si](C)(C)C(C)(C)C	2710.0	Standard non polar	33892256
(2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCCOC=C(CCC(=O)ON1C(=O)CCC1=O)O[Si](C)(C)C(C)(C)C	3291.3	Standard 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) 5-(2-hydroxyethoxy)-4-oxopentanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-6900000000-b5a65fc5d3727464e8a4	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	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 - (2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate 10V, Negative-QTOF	splash10-0fk9-3390000000-2d292286780e70c9ddf7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate 20V, Negative-QTOF	splash10-01ot-9500000000-cc5f949664086d9ea9b3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate 40V, Negative-QTOF	splash10-0a4l-9100000000-6d4c1e9485928b4e4fdd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate 10V, Positive-QTOF	splash10-05fr-0290000000-cfe69c0adc3b1e7d34ce	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate 20V, Positive-QTOF	splash10-014i-6910000000-a32e56c13817a2359e9e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate 40V, Positive-QTOF	splash10-014j-7900000000-77a193622dba7a863139	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)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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

113189

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

127583

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 (2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate (HMDB0242493)

MOL for HMDB0242493 ((2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate)

3D MOL for HMDB0242493 ((2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate)

3D SDF for HMDB0242493 ((2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate)

3D-SDF for HMDB0242493 ((2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate)

PDB for HMDB0242493 ((2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate)

3D PDB for HMDB0242493 ((2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate)

SMILES for HMDB0242493 ((2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate)

INCHI for HMDB0242493 ((2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate)

Structure for HMDB0242493 ((2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate)

3D Structure for HMDB0242493 ((2,5-Dioxopyrrolidin-1-yl) 5-(2-hydroxyethoxy)-4-oxopentanoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra