MiMeDB: Showing metabocard for Pyrrolidine (MMDBc0048008)

Microbial

Plant

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-04-19 21:49:35 UTC

Update Date

2025-09-17 19:36:31 UTC

Metabolite ID

MMDBc0048008

Metabolite Identification

Common Name

Pyrrolidine

Description

Pyrrolidine is found in alcoholic beverages. Pyrrolidine is widely distributed in foodstuffs in trace amts., presumably as bacterial decarboxylation produced of proline. Pyrrolidine is present in bread, milk, cheese, carrots, celery stalks, beer, spirits, coffee, caviar and fatty fish. Pyrrolidine is a flavouring agent.Pyrrolidine is a clear liquid with an unpleasant odor that is ammoniacal, fishy, shellfish-like and seaweed-like. Pyrrolidine is found naturally in the leaves of tobacco and carrot. The pyrrolidine ring structure is present in numerous natural alkaloids such as nicotine and hygrine. It is found in many pharmaceutical drugs such as procyclidine and bepridil. It also forms the basis for the racetam compounds (e.g. piracetam, aniracetam). Pyrrolidine is a pyrrolidine ring is the central structure of the amino acids proline and hydroxyproline. (Wikipedia ) Pyrrolidine has been found to be a metabolite in Xenorhabdus (PMID: 19598185 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Azacyclopentane	ChEBI
Azacyclopentane	ChEBI
Azolidine	ChEBI
Butylenimine	ChEBI
Perhydropyrrole	ChEBI
Prolamine	ChEBI
Tetrahydropyrrole	ChEBI
Tetramethylenimine	ChEBI
FEMA 3523	HMDB
Pyrrolidine hydrochloride	HMDB

Molecular Formula

C₄H₉N

Average Mass

71.121

Monoisotopic Mass

71.073499293

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C4H9N/c1-2-4-5-3-1/h5H,1-4H2

InChI Key

RWRDLPDLKQPQOW-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

Pyrrolidine
Azacycle
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

pyrrolidines (CHEBI:33135 )
azacycloalkane (CHEBI:33135 )
saturated organic heteromonocyclic parent (CHEBI:33135 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Food Additive	U.S. Food and Drug Administration	FDA

Host Biospecimen and Location

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

External Links

HMDB ID

HMDB0031641

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB007401

KNApSAcK ID

C00002037

Chemspider ID

29008

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pyrrolidine

METLIN ID

Not Available

PubChem Compound

31268

PDB ID

Not Available

ChEBI ID

33135

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Fleming J, Ghose A, Harrison PR: Molecular mechanisms of cancer prevention by selenium compounds. Nutr Cancer. 2001;40(1):42-9. doi: 10.1207/S15327914NC401_9. [PubMed:11799922 ]
Li X, Li Y, Xu W: Design, synthesis, and evaluation of novel galloyl pyrrolidine derivatives as potential anti-tumor agents. Bioorg Med Chem. 2006 Mar 1;14(5):1287-93. doi: 10.1016/j.bmc.2005.09.031. Epub 2005 Oct 4. [PubMed:16213145 ]
Natarajan M, Gibbons CF, Mohan S, Moore S, Kadhim MA: Oxidative stress signalling: a potential mediator of tumour necrosis factor alpha-induced genomic instability in primary vascular endothelial cells. Br J Radiol. 2007 Sep;80 Spec No 1:S13-22. doi: 10.1259/bjr/15316848. [PubMed:17704321 ]
Lee CH, Kim SH, Lee SM: Effect of pyrrolidine dithiocarbamate on hepatic vascular stress gene expression during ischemia and reperfusion. Eur J Pharmacol. 2008 Oct 24;595(1-3):100-7. doi: 10.1016/j.ejphar.2008.07.064. Epub 2008 Aug 9. [PubMed:18722366 ]
Hong TM, Teng LJ, Shun CT, Peng MC, Tsai JC: Induced interleukin-8 expression in gliomas by tumor-associated macrophages. J Neurooncol. 2009 Jul;93(3):289-301. doi: 10.1007/s11060-008-9786-z. Epub 2009 Jan 21. [PubMed:19156359 ]
Reimer D, Luxenburger E, Brachmann AO, Bode HB: A new type of pyrrolidine biosynthesis is involved in the late steps of xenocoumacin production in Xenorhabdus nematophila. Chembiochem. 2009 Aug 17;10(12):1997-2001. doi: 10.1002/cbic.200900187. [PubMed:19598185 ]
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 Pyrrolidine (MMDBc0048008)

MOL for #<Metabolite:0x00007f9abfb719c8>

3D MOL for #<Metabolite:0x00007f9abfb719c8>

3D SDF for #<Metabolite:0x00007f9abfb719c8>

3D-SDF for #<Metabolite:0x00007f9abfb719c8>

PDB for #<Metabolite:0x00007f9abfb719c8>

3D PDB for #<Metabolite:0x00007f9abfb719c8>

SMILES for #<Metabolite:0x00007f9abfb719c8>

INCHI for #<Metabolite:0x00007f9abfb719c8>

Structure for #<Metabolite:0x00007f9abfb719c8>

3D Structure for #<Metabolite:0x00007f9abfb719c8>