MiMeDB: Showing metabocard for 2-acetyl-1-pyrroline (MMDBc0033478)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:50:19 UTC

Update Date

2024-09-29 11:57:05 UTC

Metabolite ID

MMDBc0033478

Metabolite Identification

Common Name

2-acetyl-1-pyrroline

Description

2-Acetyl-1-pyrroline, abbreviated 2AP is an aroma compound and flavor that gives white bread, jasmine rice and basmati rice, the spice pandan (Pandanus amaryllifolius), and bread flowers (Vallaris glabra) their typical smell. 2-Acetyl-1-pyrroline and its structural homolog, 6-acetyl-2,3,4,5-tetrahydropyridine of similar smell, can be formed by Maillard reactions during heating of food such as in baked bread. Both compounds have odor thresholds below 0.06 ng/l.[Wikipedia ]

Structure

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

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

Molecular Formula

C₆H₉NO

Average Mass

111.1418

Monoisotopic Mass

111.068413915

IUPAC Name

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

Traditional Name

2-acetyl-1-pyrroline

CAS Registry Number

99583-29-6

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014l-9000000000-b2ec2a5a737593af1876	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-5900000000-ba7d8b3068bce1b47b39	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ox-9300000000-d40b8a0858de158c3dd1	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-93e30e06cf0f3fac2e9e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1900000000-c99599e8eef94b8c0068	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-3900000000-24d2c60642b551195027	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9000000000-a6046c2688bcfbb4c313	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1900000000-24735682b0a5560e64ae	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02t9-9500000000-2e635455b88717ca2f97	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9000000000-a0c8a0fe2acbc430c438	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-3900000000-7cddab0b1712fe3943e6	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014l-9100000000-a2ea5be954e40e1ce67b	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-efc17d3cfd9d54e8a0c4	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-30	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Activity	Data Source	Reference
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0031308

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

References

Synthesis Reference

Not Available

General References

Mahadevan K, Farmer L: Key odor impact compounds in three yeast extract pastes. J Agric Food Chem. 2006 Sep 20;54(19):7242-50. doi: 10.1021/jf061102x. [PubMed:16968089 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for 2-acetyl-1-pyrroline (MMDBc0033478)

MOL for #<Metabolite:0x00007fdb723fd1a8>

3D MOL for #<Metabolite:0x00007fdb723fd1a8>

3D SDF for #<Metabolite:0x00007fdb723fd1a8>

3D-SDF for #<Metabolite:0x00007fdb723fd1a8>

PDB for #<Metabolite:0x00007fdb723fd1a8>

3D PDB for #<Metabolite:0x00007fdb723fd1a8>

SMILES for #<Metabolite:0x00007fdb723fd1a8>

INCHI for #<Metabolite:0x00007fdb723fd1a8>

Structure for #<Metabolite:0x00007fdb723fd1a8>

3D Structure for #<Metabolite:0x00007fdb723fd1a8>