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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:44:35 UTC
Update Date2018-03-12 21:54:29 UTC
HMDB IDHMDB0031641
Secondary Accession Numbers
  • HMDB31641
Metabolite Identification
Common NamePyrrolidine
DescriptionPyrrolidine 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
Structure
Thumb
Synonyms
ValueSource
AzolidineChEBI
TetrahydropyrroleChEBI
TetramethylenimineChEBI
1-AzacyclopentaneHMDB
AzacyclopentaneHMDB
FEMA 3523HMDB
Chemical FormulaC4H9N
Average Molecular Weight71.121
Monoisotopic Molecular Weight71.073499293
IUPAC Namepyrrolidine
Traditional Namepyrrolidine
CAS Registry Number123-75-1
SMILES
C1CCNC1
InChI Identifier
InChI=1S/C4H9N/c1-2-4-5-3-1/h5H,1-4H2
InChI KeyRWRDLPDLKQPQOW-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyrrolidines. These are compounds containing a pyrrolidine ring, which is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassNot Available
Direct ParentPyrrolidines
Alternative Parents
Substituents
  • Pyrrolidine
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-63 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility291 g/LALOGPS
logP0.16ALOGPS
logP0.21ChemAxon
logS0.61ALOGPS
pKa (Strongest Basic)11.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity22.23 m³·mol⁻¹ChemAxon
Polarizability8.58 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fu-9000000000-0159c6ac6a2707c890fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-50250fbde117c345f155View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-9a9bb68d33a6b556f753View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9000000000-4840aa812595ffd33b17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-dc4555408f7b7029c1ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-d7dcf188af1b7f8ac9b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udl-9000000000-0e5b8e3fe42b29779d06View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008290
KNApSAcK IDNot Available
Chemspider ID29008
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPyrrolidine
METLIN IDNot Available
PubChem Compound31268
PDB IDVES
ChEBI ID33135
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Fleming J, Ghose A, Harrison PR: Molecular mechanisms of cancer prevention by selenium compounds. Nutr Cancer. 2001;40(1):42-9. [PubMed:11799922 ]
  2. 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 ]
  3. 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. Epub 2005 Oct 4. [PubMed:16213145 ]
  4. 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 ]
  5. 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. [PubMed:17704321 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .