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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:06:28 UTC

Update Date

2022-09-22 17:44:26 UTC

HMDB ID

HMDB0256585

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Piracetam

Description

Piracetam, also known as myocalm, 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 Piracetam. This compound has been identified in human blood as reported by (PMID: 31557052 ). Piracetam is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Piracetam 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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Myocalm	Kegg
AbZ brand OF piracetam	MeSH
Almirall brand OF piracetam	MeSH
Alpharma brand OF piracetam	MeSH
Cerepar N	MeSH
Cuxabrain	MeSH
Hormona brand OF piracetam	MeSH
Nootropil	MeSH
Normabraïn	MeSH
Pfizer brand OF piracetam	MeSH
Piracebral	MeSH
Piracetam abz	MeSH
Piracetrop	MeSH
Pirazetam	MeSH
2-Pyrrolidone-N-acetamide	MeSH
Gabacet	MeSH
memo-Puren	MeSH
Merckle brand OF piracetam	MeSH
Nootropyl	MeSH
Piracetam RPH	MeSH
Pyramem	MeSH
Riemser brand OF piracetam	MeSH
Avigilen	MeSH
Azupharma brand OF piracetam	MeSH
Cerebroforte	MeSH
Hexal brand OF piracetam	MeSH
Holsten brand OF piracetam	MeSH
Sanofi synthelabo brand OF piracetam	MeSH
TAD brand OF piracetam	MeSH
UCB brand OF piracetam	MeSH
Vedim brand OF piracetam	MeSH
Axonyl	MeSH
Ciclofalina	MeSH
Dinagen	MeSH
Geram	MeSH
memo Puren	MeSH
Nootrop	MeSH
Piracetam-RPH	MeSH
Pyracetam	MeSH
Rodleben brand OF piracetam	MeSH
Sinapsan	MeSH
2-(2-Oxopyrrolidin-1-yl)ethanimidate	Generator

Chemical Formula

C₆H₁₀N₂O₂

Average Molecular Weight

142.1558

Monoisotopic Molecular Weight

142.074227574

IUPAC Name

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

Traditional Name

piracetam

CAS Registry Number

Not Available

SMILES

OC(=N)CN1CCCC1=O

InChI Identifier

InChI=1S/C6H10N2O2/c7-5(9)4-8-3-1-2-6(8)10/h1-4H2,(H2,7,9)

InChI Key

GMZVRMREEHBGGF-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
N-alkylpyrrolidine
2-pyrrolidone
Pyrrolidone
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Primary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
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: HMDB0256585)

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	-1.4	ALOGPS
logP	-2	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	5.24	ChemAxon
pKa (Strongest Basic)	7.69	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	2	ChemAxon
Refractivity	46 m³·mol⁻¹	ChemAxon
Polarizability	13.95 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]+	130.251	30932474
DeepCCS	[M-H]-	127.022	30932474
DeepCCS	[M-2H]-	163.853	30932474
DeepCCS	[M+Na]+	138.954	30932474
AllCCS	[M+H]+	130.2	32859911
AllCCS	[M+H-H2O]+	125.8	32859911
AllCCS	[M+NH4]+	134.4	32859911
AllCCS	[M+Na]+	135.6	32859911
AllCCS	[M-H]-	127.2	32859911
AllCCS	[M+Na-2H]-	129.0	32859911
AllCCS	[M+HCOO]-	131.0	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.	2.1 minutes	32390414
Predicted by Siyang on May 30, 2022	8.4974 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.56 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	816.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	284.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	80.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	173.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	64.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	234.7 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	262.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	450.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	572.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	74.0 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	719.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	180.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	178.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	516.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	310.7 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	176.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Piracetam	OC(=N)CN1CCCC1=O	2361.3	Standard polar	33892256
Piracetam	OC(=N)CN1CCCC1=O	1642.2	Standard non polar	33892256
Piracetam	OC(=N)CN1CCCC1=O	1635.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Piracetam,2TMS,isomer #1	C[Si](C)(C)N=C(CN1CCCC1=O)O[Si](C)(C)C	1719.6	Semi standard non polar	33892256
Piracetam,2TMS,isomer #1	C[Si](C)(C)N=C(CN1CCCC1=O)O[Si](C)(C)C	1654.1	Standard non polar	33892256
Piracetam,2TMS,isomer #1	C[Si](C)(C)N=C(CN1CCCC1=O)O[Si](C)(C)C	2233.8	Standard polar	33892256
Piracetam,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(CN1CCCC1=O)O[Si](C)(C)C(C)(C)C	2123.4	Semi standard non polar	33892256
Piracetam,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(CN1CCCC1=O)O[Si](C)(C)C(C)(C)C	2084.0	Standard non polar	33892256
Piracetam,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C(CN1CCCC1=O)O[Si](C)(C)C(C)(C)C	2322.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Piracetam GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9100000000-91608c882f3d933f448d	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piracetam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piracetam GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piracetam GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piracetam GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piracetam GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piracetam LC-ESI-QFT , positive-QTOF	splash10-002b-9400000000-651dc28016b653b55d23	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piracetam LC-ESI-QFT , positive-QTOF	splash10-002b-9400000000-9c47f9c6616fbfad2c93	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piracetam LC-ESI-QFT , positive-QTOF	splash10-0002-9100000000-079c7eb43e2dcfe07d5f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piracetam LC-ESI-QFT , positive-QTOF	splash10-0002-9000000000-94d697783ea2c537498f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piracetam LC-ESI-QFT , positive-QTOF	splash10-0002-9000000000-5dd797bddeacd8764c16	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piracetam LC-ESI-QFT , positive-QTOF	splash10-006t-9000000000-e270872ffd02b3d53ab2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piracetam 90V, Positive-QTOF	splash10-006t-9000000000-0e9ffa0c462ebcb24c98	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piracetam 75V, Positive-QTOF	splash10-0002-9000000000-d11cc02b12a44a1b0d59	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piracetam 45V, Positive-QTOF	splash10-0002-9100000000-f4ffa04f1852ef6412cc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piracetam 60V, Positive-QTOF	splash10-0002-9000000000-2059b9ff4235f06ea33e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piracetam 30V, Positive-QTOF	splash10-002b-9400000000-8f8228043062c25afc06	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piracetam 10V, Positive-QTOF	splash10-0005-8900000000-155fdc4c7c8d2caf2b26	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piracetam 20V, Positive-QTOF	splash10-0002-9100000000-37719f73983f0ee54ead	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piracetam 40V, Positive-QTOF	splash10-0002-9000000000-fef9a3341f7dc53b526c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piracetam 10V, Negative-QTOF	splash10-0006-1900000000-94ddc126d9251413a02c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piracetam 20V, Negative-QTOF	splash10-0006-6900000000-e744f388669024ef6d66	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piracetam 40V, Negative-QTOF	splash10-0006-9000000000-7c593ee3fff4a54ba40d	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

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

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB09210

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4677

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Piracetam

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

rw1771551

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 Piracetam (HMDB0256585)

MOL for HMDB0256585 (Piracetam)

3D MOL for HMDB0256585 (Piracetam)

3D SDF for HMDB0256585 (Piracetam)

3D-SDF for HMDB0256585 (Piracetam)

PDB for HMDB0256585 (Piracetam)

3D PDB for HMDB0256585 (Piracetam)

SMILES for HMDB0256585 (Piracetam)

INCHI for HMDB0256585 (Piracetam)

Structure for HMDB0256585 (Piracetam)

3D Structure for HMDB0256585 (Piracetam)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra