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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2013-12-16 17:03:32 UTC

Update Date

2023-02-21 17:30:23 UTC

HMDB ID

HMDB0061384

Secondary Accession Numbers

HMDB61384

Metabolite Identification

Common Name

N-(3-acetamidopropyl)pyrrolidin-2-one

Description

N-(3-acetamidopropyl)pyrrolidin-2-one is a catabolic product of spermidine and is formed from N1-acetylspermidine. It is classified as a member of the N-alkylpyrrolidines. N-alkylpyrrolidines are compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. N-(3-acetamidopropyl)pyrrolidin-2-one is considered to be soluble (in water) and relatively neutral. (Chemosummarizer) It is excreted in the urine. The urinary level of N-(3-acetamidopropyl)pyrrolidin-2-one is increased in patients with non-Hodgkin's lymphoma.

Structure

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

HMDB0061384
     RDKit          3D
N-(3-acetamidopropyl)pyrrolidin-2-one
 29 29  0  0  0  0  0  0  0  0999 V2000
    5.1778   -0.3788    0.7836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1612    0.7088    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5943    1.8710    0.7102 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9661    0.3180   -0.1409 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8302   -0.0534   -0.6762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5218    0.2939    0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5791   -0.2665   -0.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8922   -0.0741   -0.3218 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5932   -1.0103    0.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0258   -0.6264    0.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1795    0.5192   -0.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7902    1.0148   -0.5332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3771    2.1738   -0.8202 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2359   -0.3043    1.8839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7299   -1.3382    0.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1140   -0.1405    0.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5820    1.6301   -0.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7554   -1.2071   -0.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6245    0.2739   -1.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4518    1.3741    0.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167   -0.1906    1.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4056    0.1719   -1.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3283   -1.3582   -0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5002   -2.0501    0.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1074   -1.0016    1.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3474   -0.2678    1.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6983   -1.4736    0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8676    1.3027    0.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5701    0.0892   -1.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12  8  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END

HMDB0061384
     RDKit          3D
N-(3-acetamidopropyl)pyrrolidin-2-one
 29 29  0  0  0  0  0  0  0  0999 V2000
    5.1778   -0.3788    0.7836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1612    0.7088    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5943    1.8710    0.7102 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9661    0.3180   -0.1409 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8302   -0.0534   -0.6762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5218    0.2939    0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5791   -0.2665   -0.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8922   -0.0741   -0.3218 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5932   -1.0103    0.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0258   -0.6264    0.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1795    0.5192   -0.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7902    1.0148   -0.5332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3771    2.1738   -0.8202 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2359   -0.3043    1.8839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7299   -1.3382    0.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1140   -0.1405    0.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5820    1.6301   -0.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7554   -1.2071   -0.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6245    0.2739   -1.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4518    1.3741    0.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167   -0.1906    1.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4056    0.1719   -1.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3283   -1.3582   -0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5002   -2.0501    0.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1074   -1.0016    1.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3474   -0.2678    1.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6983   -1.4736    0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8676    1.3027    0.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5701    0.0892   -1.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12  8  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END

HEADER    PROTEIN                                 16-DEC-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-DEC-13         0                                  
HETATM    1  C   UNK     0       1.494   3.025   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.056   2.474   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       0.137   0.936   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.625   0.537   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.463   1.829   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.893   4.513   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.277   3.244   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.611   2.474   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.611   0.934   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -3.945   0.164   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -5.278   0.934   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.278   2.474   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -6.612   0.164   0.000  0.00  0.00           C+0
CONECT    1    2    5    6                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    1    4                                                       
CONECT    6    1                                                            
CONECT    7    2    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0061384
HETATM    1  C1  UNL     1       5.178  -0.379   0.784  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.161   0.709   0.422  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.594   1.871   0.710  1.00  0.00           O  
HETATM    4  N1  UNL     1       2.966   0.318  -0.141  1.00  0.00           N  
HETATM    5  C3  UNL     1       1.830  -0.053  -0.676  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.522   0.294   0.063  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.579  -0.267  -0.825  1.00  0.00           C  
HETATM    8  N2  UNL     1      -1.892  -0.074  -0.322  1.00  0.00           N  
HETATM    9  C6  UNL     1      -2.593  -1.010   0.539  1.00  0.00           C  
HETATM   10  C7  UNL     1      -4.026  -0.626   0.601  1.00  0.00           C  
HETATM   11  C8  UNL     1      -4.179   0.519  -0.356  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.790   1.015  -0.533  1.00  0.00           C  
HETATM   13  O2  UNL     1      -2.377   2.174  -0.820  1.00  0.00           O  
HETATM   14  H1  UNL     1       5.236  -0.304   1.884  1.00  0.00           H  
HETATM   15  H2  UNL     1       4.730  -1.338   0.502  1.00  0.00           H  
HETATM   16  H3  UNL     1       6.114  -0.141   0.271  1.00  0.00           H  
HETATM   17  H4  UNL     1       2.582   1.630  -0.199  1.00  0.00           H  
HETATM   18  H5  UNL     1       1.755  -1.207  -0.720  1.00  0.00           H  
HETATM   19  H6  UNL     1       1.624   0.274  -1.739  1.00  0.00           H  
HETATM   20  H7  UNL     1       0.452   1.374   0.220  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.517  -0.191   1.053  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.406   0.172  -1.836  1.00  0.00           H  
HETATM   23  H10 UNL     1      -0.328  -1.358  -0.965  1.00  0.00           H  
HETATM   24  H11 UNL     1      -2.500  -2.050   0.144  1.00  0.00           H  
HETATM   25  H12 UNL     1      -2.107  -1.002   1.550  1.00  0.00           H  
HETATM   26  H13 UNL     1      -4.347  -0.268   1.610  1.00  0.00           H  
HETATM   27  H14 UNL     1      -4.698  -1.474   0.303  1.00  0.00           H  
HETATM   28  H15 UNL     1      -4.868   1.303   0.035  1.00  0.00           H  
HETATM   29  H16 UNL     1      -4.570   0.089  -1.315  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    3    4
CONECT    4    5   17
CONECT    5    6   18   19
CONECT    6    7   20   21
CONECT    7    8   22   23
CONECT    8    9   12
CONECT    9   10   24   25
CONECT   10   11   26   27
CONECT   11   12   28   29
CONECT   12   13   13
END

HMDB0061384
     RDKit          3D
N-(3-acetamidopropyl)pyrrolidin-2-one
 29 29  0  0  0  0  0  0  0  0999 V2000
    5.1778   -0.3788    0.7836 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1612    0.7088    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5943    1.8710    0.7102 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9661    0.3180   -0.1409 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8302   -0.0534   -0.6762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5218    0.2939    0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5791   -0.2665   -0.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8922   -0.0741   -0.3218 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5932   -1.0103    0.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0258   -0.6264    0.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1795    0.5192   -0.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7902    1.0148   -0.5332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3771    2.1738   -0.8202 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2359   -0.3043    1.8839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7299   -1.3382    0.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1140   -0.1405    0.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5820    1.6301   -0.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7554   -1.2071   -0.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6245    0.2739   -1.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4518    1.3741    0.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167   -0.1906    1.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4056    0.1719   -1.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3283   -1.3582   -0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5002   -2.0501    0.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1074   -1.0016    1.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3474   -0.2678    1.6099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6983   -1.4736    0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8676    1.3027    0.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5701    0.0892   -1.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12  8  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Acisoga	ChEBI
N-(3-Acetylaminopropyl)pyrrolidin-2-one	ChEBI
N-Acetylisoputreanine-gamma-lactam	ChEBI
N-Acetylisoputreanine-g-lactam	Generator
N-Acetylisoputreanine-γ-lactam	Generator

Chemical Formula

C₉H₁₆N₂O₂

Average Molecular Weight

184.2355

Monoisotopic Molecular Weight

184.121177766

IUPAC Name

N-[3-(2-oxopyrrolidin-1-yl)propyl]acetamide

Traditional Name

N-[3-(2-oxopyrrolidin-1-yl)propyl]acetamide

CAS Registry Number

106692-36-8

SMILES

CC(=O)NCCCN1CCCC1=O

InChI Identifier

InChI=1S/C9H16N2O2/c1-8(12)10-5-3-7-11-6-2-4-9(11)13/h2-7H2,1H3,(H,10,12)

InChI Key

OAUYENAPBFTAQT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-alkylpyrrolidines. N-alkylpyrrolidines are compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolidines

Sub Class

N-alkylpyrrolidines

Direct Parent

N-alkylpyrrolidines

Alternative Parents

Substituents

Pyrrolidone
2-pyrrolidone
N-alkylpyrrolidine
Tertiary carboxylic acid amide
Acetamide
Carboxamide group
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 3558558)
Feces (PMID: 27543620)

Source

Exogenous

Exogenous (HMDB: HMDB0061384)

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
Water Solubility	25 g/L	ALOGPS
logP	-0.58	ALOGPS
logP	-1.3	ChemAxon
logS	-0.87	ALOGPS
pKa (Strongest Acidic)	15.97	ChemAxon
pKa (Strongest Basic)	-0.28	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.41 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	49.41 m³·mol⁻¹	ChemAxon
Polarizability	20.4 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
DarkChem	[M+H]+	143.073	31661259
DarkChem	[M-H]-	138.96	31661259
DeepCCS	[M+H]+	139.397	30932474
DeepCCS	[M-H]-	135.746	30932474
DeepCCS	[M-2H]-	172.84	30932474
DeepCCS	[M+Na]+	148.23	30932474
AllCCS	[M+H]+	140.3	32859911
AllCCS	[M+H-H2O]+	136.4	32859911
AllCCS	[M+NH4]+	144.0	32859911
AllCCS	[M+Na]+	145.0	32859911
AllCCS	[M-H]-	142.9	32859911
AllCCS	[M+Na-2H]-	144.0	32859911
AllCCS	[M+HCOO]-	145.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.69 minutes	32390414
Predicted by Siyang on May 30, 2022	8.9894 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.93 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	964.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	235.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	103.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	160.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	63.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	206.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	283.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	493.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	622.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	153.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	928.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	195.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	188.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	476.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	302.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	111.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-(3-acetamidopropyl)pyrrolidin-2-one	CC(=O)NCCCN1CCCC1=O	2674.0	Standard polar	33892256
N-(3-acetamidopropyl)pyrrolidin-2-one	CC(=O)NCCCN1CCCC1=O	1869.1	Standard non polar	33892256
N-(3-acetamidopropyl)pyrrolidin-2-one	CC(=O)NCCCN1CCCC1=O	1884.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-(3-acetamidopropyl)pyrrolidin-2-one,1TMS,isomer #1	CC(=O)N(CCCN1CCCC1=O)[Si](C)(C)C	1864.6	Semi standard non polar	33892256
N-(3-acetamidopropyl)pyrrolidin-2-one,1TMS,isomer #1	CC(=O)N(CCCN1CCCC1=O)[Si](C)(C)C	1811.5	Standard non polar	33892256
N-(3-acetamidopropyl)pyrrolidin-2-one,1TMS,isomer #1	CC(=O)N(CCCN1CCCC1=O)[Si](C)(C)C	2497.9	Standard polar	33892256
N-(3-acetamidopropyl)pyrrolidin-2-one,1TBDMS,isomer #1	CC(=O)N(CCCN1CCCC1=O)[Si](C)(C)C(C)(C)C	2047.0	Semi standard non polar	33892256
N-(3-acetamidopropyl)pyrrolidin-2-one,1TBDMS,isomer #1	CC(=O)N(CCCN1CCCC1=O)[Si](C)(C)C(C)(C)C	2069.5	Standard non polar	33892256
N-(3-acetamidopropyl)pyrrolidin-2-one,1TBDMS,isomer #1	CC(=O)N(CCCN1CCCC1=O)[Si](C)(C)C(C)(C)C	2582.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-(3-acetamidopropyl)pyrrolidin-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-9200000000-385c37bd7fab5d058e2c	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(3-acetamidopropyl)pyrrolidin-2-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(3-acetamidopropyl)pyrrolidin-2-one 10V, Positive-QTOF	splash10-000f-0900000000-6d4904ca1c158e341fb2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(3-acetamidopropyl)pyrrolidin-2-one 20V, Positive-QTOF	splash10-0006-3900000000-5eb662408698661d8fae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(3-acetamidopropyl)pyrrolidin-2-one 40V, Positive-QTOF	splash10-0a4l-9100000000-ddb1976feb52f4d8ecc9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(3-acetamidopropyl)pyrrolidin-2-one 10V, Negative-QTOF	splash10-001i-2900000000-17c5043f9ba3f529ae83	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(3-acetamidopropyl)pyrrolidin-2-one 20V, Negative-QTOF	splash10-001l-5900000000-baf3a9b62dfd996bee8b	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(3-acetamidopropyl)pyrrolidin-2-one 40V, Negative-QTOF	splash10-0536-9000000000-ca5c68f6b2e7b7c13c6e	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(3-acetamidopropyl)pyrrolidin-2-one 10V, Positive-QTOF	splash10-002r-1900000000-1846cc5287d7976eb80b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(3-acetamidopropyl)pyrrolidin-2-one 20V, Positive-QTOF	splash10-004j-7900000000-093dbd3325b791cde4b8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(3-acetamidopropyl)pyrrolidin-2-one 40V, Positive-QTOF	splash10-0a4m-9100000000-132eac1d218d7fdf0d72	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(3-acetamidopropyl)pyrrolidin-2-one 10V, Negative-QTOF	splash10-001i-2900000000-ab4220ff6d09a2686730	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(3-acetamidopropyl)pyrrolidin-2-one 20V, Negative-QTOF	splash10-0a59-9800000000-9c3f5e5a99bf10f22782	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-(3-acetamidopropyl)pyrrolidin-2-one 40V, Negative-QTOF	splash10-0006-9000000000-3bd52f6fd30b15ca614c	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	0.65 (0.41-1.57) umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	3558558	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Non-Hodgkin's lymphoma	2061374	details

Associated Disorders and Diseases

Disease References

Non-Hodgkin's lymphoma
Hessels J, Kingma AW, Sturkenboom MC, Elzinga H, van den Berg GA, Muskiet FA: Gas chromatographic determination of N-acetylisoputreanine-gamma-lactam, a unique catabolite of N1-acetylspermidine. J Chromatogr. 1991 Jan 18;563(1):1-9. [PubMed:2061374 ]

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129397

PDB ID

Not Available

ChEBI ID

133185

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

van den Berg GA, Kingma AW, Elzinga H, Muskiet FA: Determination of N-(3-acetamidopropyl)pyrrolidin-2-one, a metabolite of spermidine, in urine by isotope dilution mass fragmentography. J Chromatogr. 1986 Dec 19;383(2):251-8. [PubMed:3558558 ]
Seiler N, Knodgen B, Haegele K: N-(3-aminopropyl)pyrrolidin-2-one, a product of spermidine catabolism in vivo. Biochem J. 1982 Oct 15;208(1):189-97. [PubMed:7159392 ]

Showing metabocard for N-(3-acetamidopropyl)pyrrolidin-2-one (HMDB0061384)

MOL for HMDB0061384 (N-(3-acetamidopropyl)pyrrolidin-2-one)

3D MOL for HMDB0061384 (N-(3-acetamidopropyl)pyrrolidin-2-one)

3D SDF for HMDB0061384 (N-(3-acetamidopropyl)pyrrolidin-2-one)

3D-SDF for HMDB0061384 (N-(3-acetamidopropyl)pyrrolidin-2-one)

PDB for HMDB0061384 (N-(3-acetamidopropyl)pyrrolidin-2-one)

3D PDB for HMDB0061384 (N-(3-acetamidopropyl)pyrrolidin-2-one)

SMILES for HMDB0061384 (N-(3-acetamidopropyl)pyrrolidin-2-one)

INCHI for HMDB0061384 (N-(3-acetamidopropyl)pyrrolidin-2-one)

Structure for HMDB0061384 (N-(3-acetamidopropyl)pyrrolidin-2-one)

3D Structure for HMDB0061384 (N-(3-acetamidopropyl)pyrrolidin-2-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra