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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:42:14 UTC

Update Date

2023-02-21 17:20:19 UTC

HMDB ID

HMDB0031308

Secondary Accession Numbers

HMDB31308

Metabolite Identification

Common Name

5-Acetyl-3,4-dihydro-2H-pyrrole

Description

5-Acetyl-3,4-dihydro-2H-pyrrole, also known as 2AP or APR, belongs to the class of organic compounds known as pyrrolines. Pyrrolines are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms. 5-Acetyl-3,4-dihydro-2H-pyrrole is a sweet, ham, and nut tasting compound. 5-Acetyl-3,4-dihydro-2H-pyrrole has been detected, but not quantified in, several different foods, such as breakfast cereal, cereals and cereal products, corns (Zea mays), taco, and tortilla chip. This could make 5-acetyl-3,4-dihydro-2H-pyrrole a potential biomarker for the consumption of these foods. 5-Acetyl-3,4-dihydro-2H-pyrrole is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 5-Acetyl-3,4-dihydro-2H-pyrrole.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Acetyl-4,5-dihydro-3H-pyrrole	ChEBI
2AP	ChEBI
APR	ChEBI
1-(3,4-dihydro-2H-Pyrrol-5-yl)ethanone	HMDB
1-(3,4-dihydro-2H-Pyrrol-5-yl)ethanone, 9ci	HMDB
1-Pyrroline, 2-acetyl	HMDB
2-Acetyl-1-pyrolline	HMDB
2-Acetyl-1-pyrroline	HMDB, MeSH
2-Acetylpyrroline	MeSH, HMDB

Chemical Formula

C₆H₉NO

Average Molecular Weight

111.1418

Monoisotopic Molecular Weight

111.068413915

IUPAC Name

1-(3,4-dihydro-2H-pyrrol-5-yl)ethan-1-one

Traditional Name

2-acetyl-1-pyrroline

CAS Registry Number

85213-22-5

SMILES

CC(=O)C1=NCCC1

InChI Identifier

InChI=1S/C6H9NO/c1-5(8)6-3-2-4-7-6/h2-4H2,1H3

InChI Key

DQBQWWSFRPLIAX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolines. Pyrrolines are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolines

Sub Class

Not Available

Direct Parent

Pyrrolines

Alternative Parents

Substituents

Pyrroline
Ketimine
Ketone
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Carbonyl group
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Imine
Hydrocarbon derivative
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

methyl ketone (CHEBI:67125 )
pyrroline (CHEBI:67125 )
acylimine (CHEBI:67125 )

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031308)
Cytoplasm (HMDB: HMDB0031308)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031308)

Source

Endogenous

Endogenous (HMDB: HMDB0031308)

Plant

Poaceae (HMDB: HMDB0031308)

Exogenous

Food

Food (HMDB: HMDB0031308)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereal

Corn (FooDB: FOOD00205)

Cereals and cereal products (FooDB: FOOD00858)

Snack

Tortilla chip (FooDB: FOOD00721)

Dish

Tex-mex cuisine

Taco (FooDB: FOOD00708)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	19.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	182.00 to 183.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	4103 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.019 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.09 g/L	ALOGPS
logP	0.19	ALOGPS
logP	0.86	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	18.44	ChemAxon
pKa (Strongest Basic)	3.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.43 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	31.39 m³·mol⁻¹	ChemAxon
Polarizability	12.01 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]+	123.502	31661259
DarkChem	[M-H]-	116.652	31661259
DeepCCS	[M+H]+	128.573	30932474
DeepCCS	[M-H]-	126.214	30932474
DeepCCS	[M-2H]-	161.995	30932474
DeepCCS	[M+Na]+	136.922	30932474
AllCCS	[M+H]+	121.6	32859911
AllCCS	[M+H-H2O]+	116.7	32859911
AllCCS	[M+NH4]+	126.2	32859911
AllCCS	[M+Na]+	127.5	32859911
AllCCS	[M-H]-	122.5	32859911
AllCCS	[M+Na-2H]-	125.1	32859911
AllCCS	[M+HCOO]-	127.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Acetyl-3,4-dihydro-2H-pyrrole	CC(=O)C1=NCCC1	1366.4	Standard polar	33892256
5-Acetyl-3,4-dihydro-2H-pyrrole	CC(=O)C1=NCCC1	876.7	Standard non polar	33892256
5-Acetyl-3,4-dihydro-2H-pyrrole	CC(=O)C1=NCCC1	945.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Acetyl-3,4-dihydro-2H-pyrrole,1TMS,isomer #1	C=C(O[Si](C)(C)C)C1=NCCC1	1235.9	Semi standard non polar	33892256
5-Acetyl-3,4-dihydro-2H-pyrrole,1TMS,isomer #1	C=C(O[Si](C)(C)C)C1=NCCC1	1214.2	Standard non polar	33892256
5-Acetyl-3,4-dihydro-2H-pyrrole,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C1=NCCC1	1435.7	Semi standard non polar	33892256
5-Acetyl-3,4-dihydro-2H-pyrrole,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C1=NCCC1	1414.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole GC-MS (Non-derivatized) - 70eV, Positive	splash10-014l-9000000000-b2ec2a5a737593af1876	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 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 - 5-Acetyl-3,4-dihydro-2H-pyrrole 10V, Positive-QTOF	splash10-03di-5900000000-ba7d8b3068bce1b47b39	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 20V, Positive-QTOF	splash10-01ox-9300000000-d40b8a0858de158c3dd1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 40V, Positive-QTOF	splash10-00kf-9000000000-93e30e06cf0f3fac2e9e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 10V, Negative-QTOF	splash10-03di-1900000000-c99599e8eef94b8c0068	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 20V, Negative-QTOF	splash10-03di-3900000000-24d2c60642b551195027	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 40V, Negative-QTOF	splash10-014l-9000000000-a6046c2688bcfbb4c313	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 10V, Negative-QTOF	splash10-03di-1900000000-24735682b0a5560e64ae	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 20V, Negative-QTOF	splash10-02t9-9500000000-2e635455b88717ca2f97	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 40V, Negative-QTOF	splash10-014l-9000000000-a0c8a0fe2acbc430c438	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 10V, Positive-QTOF	splash10-03di-3900000000-7cddab0b1712fe3943e6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 20V, Positive-QTOF	splash10-014l-9100000000-a2ea5be954e40e1ce67b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 40V, Positive-QTOF	splash10-0006-9000000000-efc17d3cfd9d54e8a0c4	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)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	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

FDB003364

KNApSAcK ID

Not Available

Chemspider ID

456071

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2-Acetyl-1-pyrroline

METLIN ID

Not Available

PubChem Compound

522834

PDB ID

Not Available

ChEBI ID

67125

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1583501

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 5-Acetyl-3,4-dihydro-2H-pyrrole (HMDB0031308)

MOL for HMDB0031308 (5-Acetyl-3,4-dihydro-2H-pyrrole)

3D MOL for HMDB0031308 (5-Acetyl-3,4-dihydro-2H-pyrrole)

3D SDF for HMDB0031308 (5-Acetyl-3,4-dihydro-2H-pyrrole)

3D-SDF for HMDB0031308 (5-Acetyl-3,4-dihydro-2H-pyrrole)

PDB for HMDB0031308 (5-Acetyl-3,4-dihydro-2H-pyrrole)

3D PDB for HMDB0031308 (5-Acetyl-3,4-dihydro-2H-pyrrole)

SMILES for HMDB0031308 (5-Acetyl-3,4-dihydro-2H-pyrrole)

INCHI for HMDB0031308 (5-Acetyl-3,4-dihydro-2H-pyrrole)

Structure for HMDB0031308 (5-Acetyl-3,4-dihydro-2H-pyrrole)

3D Structure for HMDB0031308 (5-Acetyl-3,4-dihydro-2H-pyrrole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra