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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 16:30:19 UTC

Update Date

2021-09-26 23:11:40 UTC

HMDB ID

HMDB0256183

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate

Description

Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate, also known as 4-phenyl-5,5-dicarbethoxy-2-pyrrolidinone or PDCP, belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids. Based on a literature review a significant number of articles have been published on Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate 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

HMDB0256183
     RDKit          3D
Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate
 41 42  0  0  0  0  0  0  0  0999 V2000
   -3.0273    3.3128   -0.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5530    3.2583   -0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8998    2.0758   -0.2924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1117    0.9223    0.5160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405    1.0605    1.4434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4155   -0.2957    0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2719   -1.3935   -0.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2355   -1.6058   -1.5769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0764   -2.1965    0.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8896   -3.2498    0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1163   -4.2574   -0.7887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2007   -0.9790    1.4139 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2058   -1.8263    0.9315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9097   -2.6239    1.6163 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3344   -1.6548   -0.5463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7472   -0.2163   -0.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8614    0.6446   -0.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7894    0.8887   -1.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9205    1.6495   -1.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1534    2.2036    0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2466    1.9792    1.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0973    1.1961    0.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3335    4.4071   -0.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3742    3.0260   -1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6248    2.8093    0.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1027    4.0589   -0.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3378    3.6433    0.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1072   -3.7997    1.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8783   -3.0531   -0.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8274   -4.8746   -1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3737   -3.7617   -1.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6087   -4.9773   -0.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0295   -0.8923    2.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7064   -2.3352   -1.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4057   -1.6165   -0.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4510   -0.0658   -1.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6395    0.4651   -2.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6595    1.8435   -1.9191 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0046    2.8170    0.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4323    2.3998    2.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3694    1.0139    1.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  6 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 16  6  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
M  END

  Mrv1652309112118302D          

 22 23  0  0  0  0            999 V2000
   -2.0035   -0.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966   -0.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6445   -0.7959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -0.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4174    0.1602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830   -3.1745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665   -1.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3381   -0.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1227   -0.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7358   -0.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5642   -1.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7796   -2.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0735   -0.7959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0116    0.1602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5636    0.7733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3706    0.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  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
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256183

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)C1(NC(=O)CC1C1=CC=CC=C1)C(=O)OCC

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO5/c1-3-21-14(19)16(15(20)22-4-2)12(10-13(18)17-16)11-8-6-5-7-9-11/h5-9,12H,3-4,10H2,1-2H3,(H,17,18)

> <INCHI_KEY>
RQXLSXSKRKTNTK-UHFFFAOYSA-N

> <FORMULA>
C16H19NO5

> <MOLECULAR_WEIGHT>
305.33

> <EXACT_MASS>
305.126322716

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.04513784610647

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,2-diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate

> <ALOGPS_LOGP>
1.72

> <JCHEM_LOGP>
1.4728307929999993

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.246953100282775

> <JCHEM_PKA_STRONGEST_BASIC>
-2.630749302885709

> <JCHEM_POLAR_SURFACE_AREA>
81.7

> <JCHEM_REFRACTIVITY>
77.88929999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,2-diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256183
     RDKit          3D
Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate
 41 42  0  0  0  0  0  0  0  0999 V2000
   -3.0273    3.3128   -0.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5530    3.2583   -0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8998    2.0758   -0.2924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1117    0.9223    0.5160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405    1.0605    1.4434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4155   -0.2957    0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2719   -1.3935   -0.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2355   -1.6058   -1.5769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0764   -2.1965    0.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8896   -3.2498    0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1163   -4.2574   -0.7887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2007   -0.9790    1.4139 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2058   -1.8263    0.9315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9097   -2.6239    1.6163 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3344   -1.6548   -0.5463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7472   -0.2163   -0.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8614    0.6446   -0.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7894    0.8887   -1.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9205    1.6495   -1.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1534    2.2036    0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2466    1.9792    1.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0973    1.1961    0.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3335    4.4071   -0.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3742    3.0260   -1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6248    2.8093    0.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1027    4.0589   -0.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3378    3.6433    0.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1072   -3.7997    1.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8783   -3.0531   -0.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8274   -4.8746   -1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3737   -3.7617   -1.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6087   -4.9773   -0.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0295   -0.8923    2.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7064   -2.3352   -1.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4057   -1.6165   -0.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4510   -0.0658   -1.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6395    0.4651   -2.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6595    1.8435   -1.9191 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0046    2.8170    0.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4323    2.3998    2.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3694    1.0139    1.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  6 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 16  6  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  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      -3.740  -0.661   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.234  -0.341   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.203  -1.486   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.303  -1.166   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.779   0.299   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.580  -3.215   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.104  -4.680   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.564  -4.680   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.342  -5.926   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       0.088  -3.215   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       4.044  -2.739   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.364  -1.233   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.829  -0.757   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.973  -1.788   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.653  -3.294   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.189  -3.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.364  -1.166   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.870  -1.486   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.888   0.299   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.919   1.444   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.425   1.123   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11   18                                             
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    6                                                       
CONECT   12    7   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    6   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0256183
HETATM    1  C1  UNL     1      -3.027   3.313  -0.233  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.553   3.258  -0.060  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.900   2.076  -0.292  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.112   0.922   0.516  1.00  0.00           C  
HETATM    5  O2  UNL     1      -1.940   1.061   1.443  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.415  -0.296   0.287  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.272  -1.393  -0.337  1.00  0.00           C  
HETATM    8  O3  UNL     1      -1.235  -1.606  -1.577  1.00  0.00           O  
HETATM    9  O4  UNL     1      -2.076  -2.197   0.413  1.00  0.00           O  
HETATM   10  C6  UNL     1      -2.890  -3.250   0.053  1.00  0.00           C  
HETATM   11  C7  UNL     1      -2.116  -4.257  -0.789  1.00  0.00           C  
HETATM   12  N1  UNL     1       0.201  -0.979   1.414  1.00  0.00           N  
HETATM   13  C8  UNL     1       1.206  -1.826   0.931  1.00  0.00           C  
HETATM   14  O5  UNL     1       1.910  -2.624   1.616  1.00  0.00           O  
HETATM   15  C9  UNL     1       1.334  -1.655  -0.546  1.00  0.00           C  
HETATM   16  C10 UNL     1       0.747  -0.216  -0.686  1.00  0.00           C  
HETATM   17  C11 UNL     1       1.861   0.645  -0.337  1.00  0.00           C  
HETATM   18  C12 UNL     1       2.789   0.889  -1.329  1.00  0.00           C  
HETATM   19  C13 UNL     1       3.921   1.649  -1.135  1.00  0.00           C  
HETATM   20  C14 UNL     1       4.153   2.204   0.101  1.00  0.00           C  
HETATM   21  C15 UNL     1       3.247   1.979   1.119  1.00  0.00           C  
HETATM   22  C16 UNL     1       2.097   1.196   0.895  1.00  0.00           C  
HETATM   23  H1  UNL     1      -3.334   4.407  -0.167  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.374   3.026  -1.253  1.00  0.00           H  
HETATM   25  H3  UNL     1      -3.625   2.809   0.515  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.103   4.059  -0.730  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.338   3.643   0.986  1.00  0.00           H  
HETATM   28  H6  UNL     1      -3.107  -3.800   1.059  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.878  -3.053  -0.335  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.827  -4.875  -1.393  1.00  0.00           H  
HETATM   31  H9  UNL     1      -1.374  -3.762  -1.406  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.609  -4.977  -0.112  1.00  0.00           H  
HETATM   33  H11 UNL     1      -0.030  -0.892   2.421  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.706  -2.335  -1.075  1.00  0.00           H  
HETATM   35  H13 UNL     1       2.406  -1.616  -0.852  1.00  0.00           H  
HETATM   36  H14 UNL     1       0.451  -0.066  -1.730  1.00  0.00           H  
HETATM   37  H15 UNL     1       2.640   0.465  -2.320  1.00  0.00           H  
HETATM   38  H16 UNL     1       4.659   1.844  -1.919  1.00  0.00           H  
HETATM   39  H17 UNL     1       5.005   2.817   0.335  1.00  0.00           H  
HETATM   40  H18 UNL     1       3.432   2.400   2.091  1.00  0.00           H  
HETATM   41  H19 UNL     1       1.369   1.014   1.684  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   12   16
CONECT    7    8    8    9
CONECT    9   10
CONECT   10   11   28   29
CONECT   11   30   31   32
CONECT   12   13   33
CONECT   13   14   14   15
CONECT   15   16   34   35
CONECT   16   17   36
CONECT   17   18   18   22
CONECT   18   19   37
CONECT   19   20   20   38
CONECT   20   21   39
CONECT   21   22   22   40
CONECT   22   41
END

HMDB0256183
     RDKit          3D
Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate
 41 42  0  0  0  0  0  0  0  0999 V2000
   -3.0273    3.3128   -0.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5530    3.2583   -0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8998    2.0758   -0.2924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1117    0.9223    0.5160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405    1.0605    1.4434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4155   -0.2957    0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2719   -1.3935   -0.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2355   -1.6058   -1.5769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0764   -2.1965    0.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8896   -3.2498    0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1163   -4.2574   -0.7887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2007   -0.9790    1.4139 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2058   -1.8263    0.9315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9097   -2.6239    1.6163 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3344   -1.6548   -0.5463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7472   -0.2163   -0.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8614    0.6446   -0.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7894    0.8887   -1.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9205    1.6495   -1.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1534    2.2036    0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2466    1.9792    1.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0973    1.1961    0.8951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3335    4.4071   -0.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3742    3.0260   -1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6248    2.8093    0.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1027    4.0589   -0.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3378    3.6433    0.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1072   -3.7997    1.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8783   -3.0531   -0.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8274   -4.8746   -1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3737   -3.7617   -1.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6087   -4.9773   -0.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0295   -0.8923    2.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7064   -2.3352   -1.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4057   -1.6165   -0.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4510   -0.0658   -1.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6395    0.4651   -2.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6595    1.8435   -1.9191 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0046    2.8170    0.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4323    2.3998    2.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3694    1.0139    1.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  6 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 16  6  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylic acid	Generator
2,2-Diethyl 5-hydroxy-3-phenyl-3,4-dihydro-2H-pyrrole-2,2-dicarboxylic acid	HMDB
4-Phenyl-5,5-dicarbethoxy-2-pyrrolidinone	HMDB
PDCP	HMDB

Chemical Formula

C₁₆H₁₉NO₅

Average Molecular Weight

305.33

Monoisotopic Molecular Weight

305.126322716

IUPAC Name

2,2-diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate

Traditional Name

2,2-diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate

CAS Registry Number

Not Available

SMILES

CCOC(=O)C1(NC(=O)CC1C1=CC=CC=C1)C(=O)OCC

InChI Identifier

InChI=1S/C16H19NO5/c1-3-21-14(19)16(15(20)22-4-2)12(10-13(18)17-16)11-8-6-5-7-9-11/h5-9,12H,3-4,10H2,1-2H3,(H,17,18)

InChI Key

RQXLSXSKRKTNTK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid esters

Alternative Parents

Substituents

Alpha-amino acid ester
3-phenylpyrrolidine
Oxoproline
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Pyrrolidone
2-pyrrolidone
Benzenoid
Pyrrolidine
Pyrrole
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid ester
Lactam
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	1.72	ALOGPS
logP	1.47	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	10.25	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	81.7 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	77.89 m³·mol⁻¹	ChemAxon
Polarizability	31.05 Å³	ChemAxon
Number of Rings	2	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]+	166.875	30932474
DeepCCS	[M-H]-	164.517	30932474
DeepCCS	[M-2H]-	198.223	30932474
DeepCCS	[M+Na]+	173.45	30932474
AllCCS	[M+H]+	169.9	32859911
AllCCS	[M+H-H2O]+	166.6	32859911
AllCCS	[M+NH4]+	173.0	32859911
AllCCS	[M+Na]+	173.9	32859911
AllCCS	[M-H]-	172.9	32859911
AllCCS	[M+Na-2H]-	172.9	32859911
AllCCS	[M+HCOO]-	173.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate	CCOC(=O)C1(NC(=O)CC1C1=CC=CC=C1)C(=O)OCC	3286.9	Standard polar	33892256
Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate	CCOC(=O)C1(NC(=O)CC1C1=CC=CC=C1)C(=O)OCC	2079.7	Standard non polar	33892256
Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate	CCOC(=O)C1(NC(=O)CC1C1=CC=CC=C1)C(=O)OCC	2255.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate,1TMS,isomer #1	CCOC(=O)C1(C(=O)OCC)C(C2=CC=CC=C2)CC(=O)N1[Si](C)(C)C	2241.2	Semi standard non polar	33892256
Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate,1TMS,isomer #1	CCOC(=O)C1(C(=O)OCC)C(C2=CC=CC=C2)CC(=O)N1[Si](C)(C)C	2196.9	Standard non polar	33892256
Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate,1TMS,isomer #1	CCOC(=O)C1(C(=O)OCC)C(C2=CC=CC=C2)CC(=O)N1[Si](C)(C)C	2997.1	Standard polar	33892256
Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate,1TBDMS,isomer #1	CCOC(=O)C1(C(=O)OCC)C(C2=CC=CC=C2)CC(=O)N1[Si](C)(C)C(C)(C)C	2478.1	Semi standard non polar	33892256
Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate,1TBDMS,isomer #1	CCOC(=O)C1(C(=O)OCC)C(C2=CC=CC=C2)CC(=O)N1[Si](C)(C)C(C)(C)C	2398.7	Standard non polar	33892256
Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate,1TBDMS,isomer #1	CCOC(=O)C1(C(=O)OCC)C(C2=CC=CC=C2)CC(=O)N1[Si](C)(C)C(C)(C)C	3037.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-7390000000-33165a93ee7f6265846e	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate 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

89070

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

98627

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 Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate (HMDB0256183)

MOL for HMDB0256183 (Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate)

3D MOL for HMDB0256183 (Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate)

3D SDF for HMDB0256183 (Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate)

3D-SDF for HMDB0256183 (Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate)

PDB for HMDB0256183 (Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate)

3D PDB for HMDB0256183 (Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate)

SMILES for HMDB0256183 (Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate)

INCHI for HMDB0256183 (Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate)

Structure for HMDB0256183 (Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate)

3D Structure for HMDB0256183 (Diethyl 5-oxo-3-phenylpyrrolidine-2,2-dicarboxylate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra