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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 09:47:09 UTC

Update Date

2021-09-26 23:04:30 UTC

HMDB ID

HMDB0252105

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Etiracetam

Description

Etiracetam belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Based on a literature review very few articles have been published on Etiracetam. This compound has been identified in human blood as reported by (PMID: 31557052 ). Etiracetam is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Etiracetam 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

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0      -3.436   3.633   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.971   3.157   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.795   0.620   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -2.475  -0.886   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -4.260   1.096   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    6                                                       
CONECT    3    4    5                                                       
CONECT    4    3    7                                                       
CONECT    5    3   10                                                       
CONECT    6    2    8   10                                                  
CONECT    7    4   10   11                                                  
CONECT    8    6    9   12                                                  
CONECT    9    8                                                            
CONECT   10    5    6    7                                                  
CONECT   11    7                                                            
CONECT   12    8                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
alpha-Ethyl-2-oxo-1-pyrrolidineacetamide	MeSH
Levetiracetam	MeSH
Ucb L060	MeSH
Ucb-L060	MeSH
Ucb-L059	MeSH
Etiracetam, S-isomer	MeSH
UCB brand OF levetiracetam	MeSH
Ucb L059	MeSH
Keppra	MeSH
Etiracetam, R-isomer	MeSH
Etiracetam, R isomer	MeSH
alpha Ethyl 2 oxo 1 pyrrolidineacetamide	MeSH
Etiracetam, S isomer	MeSH
UcbL060	MeSH
R-Isomer etiracetam	MeSH
S-Isomer etiracetam	MeSH

Chemical Formula

C₈H₁₄N₂O₂

Average Molecular Weight

170.212

Monoisotopic Molecular Weight

170.105527699

IUPAC Name

2-(2-oxopyrrolidin-1-yl)butanimidic acid

Traditional Name

etiracetam

CAS Registry Number

Not Available

SMILES

CCC(N1CCCC1=O)C(O)=N

InChI Identifier

InChI=1S/C8H14N2O2/c1-2-6(8(9)12)10-5-3-4-7(10)11/h6H,2-5H2,1H3,(H2,9,12)

InChI Key

HPHUVLMMVZITSG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

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 acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Fatty amide
Pyrrolidone
2-pyrrolidone
Fatty acyl
N-alkylpyrrolidine
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Primary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Organic oxide
Organopnictogen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
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 (HMDB: HMDB0252105)

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	-0.46	ALOGPS
logP	-2.4	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	-2.2	ChemAxon
pKa (Strongest Basic)	13.02	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	64.39 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	55.02 m³·mol⁻¹	ChemAxon
Polarizability	17.7 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]+	143.859	30932474
DeepCCS	[M-H]-	140.289	30932474
DeepCCS	[M-2H]-	177.668	30932474
DeepCCS	[M+Na]+	153.048	30932474
AllCCS	[M+H]+	138.5	32859911
AllCCS	[M+H-H2O]+	134.3	32859911
AllCCS	[M+NH4]+	142.3	32859911
AllCCS	[M+Na]+	143.4	32859911
AllCCS	[M-H]-	135.8	32859911
AllCCS	[M+Na-2H]-	137.1	32859911
AllCCS	[M+HCOO]-	138.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Etiracetam	CCC(N1CCCC1=O)C(O)=N	2365.8	Standard polar	33892256
Etiracetam	CCC(N1CCCC1=O)C(O)=N	1752.7	Standard non polar	33892256
Etiracetam	CCC(N1CCCC1=O)C(O)=N	1672.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Etiracetam,2TMS,isomer #1	CCC(C(=N[Si](C)(C)C)O[Si](C)(C)C)N1CCCC1=O	1710.4	Semi standard non polar	33892256
Etiracetam,2TMS,isomer #1	CCC(C(=N[Si](C)(C)C)O[Si](C)(C)C)N1CCCC1=O	1666.0	Standard non polar	33892256
Etiracetam,2TMS,isomer #1	CCC(C(=N[Si](C)(C)C)O[Si](C)(C)C)N1CCCC1=O	2179.7	Standard polar	33892256
Etiracetam,2TBDMS,isomer #1	CCC(C(=N[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N1CCCC1=O	2147.7	Semi standard non polar	33892256
Etiracetam,2TBDMS,isomer #1	CCC(C(=N[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N1CCCC1=O	2089.9	Standard non polar	33892256
Etiracetam,2TBDMS,isomer #1	CCC(C(=N[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)N1CCCC1=O	2324.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Etiracetam GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9300000000-8cf8dd3f899624fbbba1	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etiracetam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etiracetam GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etiracetam GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etiracetam GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etiracetam GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	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 - Etiracetam 10V, Positive-QTOF	splash10-00di-0900000000-ec0076a60bef1bfe06dd	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiracetam 20V, Positive-QTOF	splash10-0fb9-2900000000-22b720450ebfea704554	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiracetam 40V, Positive-QTOF	splash10-0006-9100000000-17a515534beb406070e0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiracetam 10V, Negative-QTOF	splash10-014i-0900000000-7470975ba67c5de6162e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiracetam 20V, Negative-QTOF	splash10-00pl-5900000000-50443438445390c4345a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiracetam 40V, Negative-QTOF	splash10-0006-9000000000-517ee6018ae48754d1b7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiracetam 10V, Positive-QTOF	splash10-004i-1900000000-0301aecbbccd662f4c13	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiracetam 20V, Positive-QTOF	splash10-004i-5900000000-cca3ef7ca1e0bddab64d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiracetam 40V, Positive-QTOF	splash10-00yu-9000000000-a0a085321d186b60c41c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiracetam 10V, Negative-QTOF	splash10-014i-1900000000-edd5c590dab655fc4e66	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiracetam 20V, Negative-QTOF	splash10-0159-9100000000-b68f9c33cfdcf7208176	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etiracetam 40V, Negative-QTOF	splash10-0006-9200000000-6aae8618202e2be86cf8	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB11868

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

53863

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Etiracetam

METLIN ID

Not Available

PubChem Compound

Not Available

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 Etiracetam (HMDB0252105)

MOL for HMDB0252105 (Etiracetam)

3D MOL for HMDB0252105 (Etiracetam)

3D SDF for HMDB0252105 (Etiracetam)

3D-SDF for HMDB0252105 (Etiracetam)

PDB for HMDB0252105 (Etiracetam)

3D PDB for HMDB0252105 (Etiracetam)

SMILES for HMDB0252105 (Etiracetam)

INCHI for HMDB0252105 (Etiracetam)

Structure for HMDB0252105 (Etiracetam)

3D Structure for HMDB0252105 (Etiracetam)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra