Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:32:00 UTC

Update Date

2023-02-21 17:25:47 UTC

HMDB ID

HMDB0037293

Secondary Accession Numbers

HMDB37293

Metabolite Identification

Common Name

2-Acetylpyrrolidine

Description

2-Acetylpyrrolidine belongs to the class of organic compounds known as pyrrolidines. Pyrrolidines are compounds containing a pyrrolidine ring, which is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. 2-Acetylpyrrolidine has been detected, but not quantified in, breakfast cereal and cereals and cereal products. This could make 2-acetylpyrrolidine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Acetylpyrrolidine.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-(2-Pyrrolidinyl)ethanone	HMDB
1-(2-Pyrrolidinyl)ethanone, 9ci	HMDB

Chemical Formula

C₆H₁₁NO

Average Molecular Weight

113.1576

Monoisotopic Molecular Weight

113.084063979

IUPAC Name

1-(pyrrolidin-2-yl)ethan-1-one

Traditional Name

1-(pyrrolidin-2-yl)ethanone

CAS Registry Number

60026-20-2

SMILES

CC(=O)C1CCCN1

InChI Identifier

InChI=1S/C6H11NO/c1-5(8)6-3-2-4-7-6/h6-7H,2-4H2,1H3

InChI Key

FYCFJMPASVKULQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolidines. Pyrrolidines are compounds containing a pyrrolidine ring, which 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

Not Available

Direct Parent

Pyrrolidines

Alternative Parents

Substituents

Alpha-aminoketone
Pyrrolidine
Ketone
Secondary aliphatic amine
Secondary amine
Azacycle
Organic nitrogen compound
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Amine
Hydrocarbon derivative
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037293)
Cytoplasm (HMDB: HMDB0037293)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037293)

Source

Exogenous

Exogenous (HMDB: HMDB0037293)

Food

Food (HMDB: HMDB0037293)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Endogenous

Plant

Poaceae (HMDB: HMDB0037293)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037293)

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	228 g/L	ALOGPS
logP	-0.16	ALOGPS
logP	0.23	ChemAxon
logS	0.3	ALOGPS
pKa (Strongest Acidic)	17.84	ChemAxon
pKa (Strongest Basic)	9.57	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.1 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	31.62 m³·mol⁻¹	ChemAxon
Polarizability	12.6 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	123.22	31661259
DarkChem	[M-H]-	117.238	31661259
DeepCCS	[M+H]+	121.363	30932474
DeepCCS	[M-H]-	118.409	30932474
DeepCCS	[M-2H]-	155.049	30932474
DeepCCS	[M+Na]+	129.932	30932474
AllCCS	[M+H]+	123.1	32859911
AllCCS	[M+H-H2O]+	118.3	32859911
AllCCS	[M+NH4]+	127.7	32859911
AllCCS	[M+Na]+	129.0	32859911
AllCCS	[M-H]-	123.2	32859911
AllCCS	[M+Na-2H]-	125.8	32859911
AllCCS	[M+HCOO]-	128.7	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.	1.72 minutes	32390414
Predicted by Siyang on May 30, 2022	8.2916 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.02 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	230.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	629.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	293.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	85.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	182.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	51.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	255.5 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	246.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	605.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	576.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	92.3 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	632.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	182.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	202.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	703.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	417.1 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	214.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Acetylpyrrolidine	CC(=O)C1CCCN1	1515.6	Standard polar	33892256
2-Acetylpyrrolidine	CC(=O)C1CCCN1	928.6	Standard non polar	33892256
2-Acetylpyrrolidine	CC(=O)C1CCCN1	1069.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Acetylpyrrolidine,1TMS,isomer #1	CC(O[Si](C)(C)C)=C1CCCN1	1346.0	Semi standard non polar	33892256
2-Acetylpyrrolidine,1TMS,isomer #1	CC(O[Si](C)(C)C)=C1CCCN1	1286.4	Standard non polar	33892256
2-Acetylpyrrolidine,1TMS,isomer #2	C=C(O[Si](C)(C)C)C1CCCN1	1131.4	Semi standard non polar	33892256
2-Acetylpyrrolidine,1TMS,isomer #2	C=C(O[Si](C)(C)C)C1CCCN1	1244.7	Standard non polar	33892256
2-Acetylpyrrolidine,1TMS,isomer #3	CC(=O)C1CCCN1[Si](C)(C)C	1154.8	Semi standard non polar	33892256
2-Acetylpyrrolidine,1TMS,isomer #3	CC(=O)C1CCCN1[Si](C)(C)C	1213.6	Standard non polar	33892256
2-Acetylpyrrolidine,2TMS,isomer #1	CC(O[Si](C)(C)C)=C1CCCN1[Si](C)(C)C	1429.7	Semi standard non polar	33892256
2-Acetylpyrrolidine,2TMS,isomer #1	CC(O[Si](C)(C)C)=C1CCCN1[Si](C)(C)C	1393.2	Standard non polar	33892256
2-Acetylpyrrolidine,2TMS,isomer #2	C=C(O[Si](C)(C)C)C1CCCN1[Si](C)(C)C	1280.1	Semi standard non polar	33892256
2-Acetylpyrrolidine,2TMS,isomer #2	C=C(O[Si](C)(C)C)C1CCCN1[Si](C)(C)C	1352.8	Standard non polar	33892256
2-Acetylpyrrolidine,1TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CCCN1	1536.1	Semi standard non polar	33892256
2-Acetylpyrrolidine,1TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CCCN1	1484.2	Standard non polar	33892256
2-Acetylpyrrolidine,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C1CCCN1	1365.2	Semi standard non polar	33892256
2-Acetylpyrrolidine,1TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C1CCCN1	1404.4	Standard non polar	33892256
2-Acetylpyrrolidine,1TBDMS,isomer #3	CC(=O)C1CCCN1[Si](C)(C)C(C)(C)C	1402.3	Semi standard non polar	33892256
2-Acetylpyrrolidine,1TBDMS,isomer #3	CC(=O)C1CCCN1[Si](C)(C)C(C)(C)C	1470.3	Standard non polar	33892256
2-Acetylpyrrolidine,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CCCN1[Si](C)(C)C(C)(C)C	1881.3	Semi standard non polar	33892256
2-Acetylpyrrolidine,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CCCN1[Si](C)(C)C(C)(C)C	1807.2	Standard non polar	33892256
2-Acetylpyrrolidine,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C1CCCN1[Si](C)(C)C(C)(C)C	1733.4	Semi standard non polar	33892256
2-Acetylpyrrolidine,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)C1CCCN1[Si](C)(C)C(C)(C)C	1737.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Acetylpyrrolidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9000000000-f27ccdf0b440cb128373	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Acetylpyrrolidine 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 - 2-Acetylpyrrolidine 10V, Positive-QTOF	splash10-03di-5900000000-ad558e7396d088fc1a2c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetylpyrrolidine 20V, Positive-QTOF	splash10-03dj-9500000000-0dc2bf1f0cda784cfd99	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetylpyrrolidine 40V, Positive-QTOF	splash10-006x-9000000000-2c2abaf996477b5a5baa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetylpyrrolidine 10V, Negative-QTOF	splash10-03di-1900000000-4b95b7161e9408e3c1b8	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetylpyrrolidine 20V, Negative-QTOF	splash10-03di-3900000000-2f7b3ace0ed0d75d16cc	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetylpyrrolidine 40V, Negative-QTOF	splash10-0006-9000000000-e804646fc07f7e32d20b	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetylpyrrolidine 10V, Negative-QTOF	splash10-03di-0900000000-7ca3d0aa73039ede6ec3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetylpyrrolidine 20V, Negative-QTOF	splash10-01ox-9600000000-248675faf1b3ecfae204	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetylpyrrolidine 40V, Negative-QTOF	splash10-0006-9000000000-4f52db10ebceaa95cc6c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetylpyrrolidine 10V, Positive-QTOF	splash10-03di-7900000000-e241cc067f2bfa80eff6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetylpyrrolidine 20V, Positive-QTOF	splash10-00di-9000000000-4394e1a7d3139d076819	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetylpyrrolidine 40V, Positive-QTOF	splash10-002f-9000000000-39c6c40c92fe17b902bb	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB016312

KNApSAcK ID

Not Available

Chemspider ID

479117

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

550747

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2-Acetylpyrrolidine (HMDB0037293)

MOL for HMDB0037293 (2-Acetylpyrrolidine)

3D MOL for HMDB0037293 (2-Acetylpyrrolidine)

3D SDF for HMDB0037293 (2-Acetylpyrrolidine)

3D-SDF for HMDB0037293 (2-Acetylpyrrolidine)

PDB for HMDB0037293 (2-Acetylpyrrolidine)

3D PDB for HMDB0037293 (2-Acetylpyrrolidine)

SMILES for HMDB0037293 (2-Acetylpyrrolidine)

INCHI for HMDB0037293 (2-Acetylpyrrolidine)

Structure for HMDB0037293 (2-Acetylpyrrolidine)

3D Structure for HMDB0037293 (2-Acetylpyrrolidine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra