Showing Compound Card for Pyrrolidine (CDB000090)

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Record Information
Version1.0
Created at2020-03-18 23:24:24 UTC
Updated at2020-12-07 19:07:05 UTC
CannabisDB IDCDB000090
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePyrrolidine
DescriptionPyrrolidine, also known as azolidine, belongs to the class of organic compounds known as pyrrolidines which contain a pyrrolidine ring, a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. The pyrrolidine ring is the central structure of the amino acids, proline and hydroxyproline. The pyrrolidine ring structure is present in numerous natural alkaloids such as nicotine and hygrine and 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 strong basic compound and is soluble in most organic solvents. Pyrrolidine is a clear liquid with an unpleasant ammoniacal, fishy, shellfish-like taste and seaweed-like odor ( Ref:DOI ). Pyrrolidine is found naturally in the leaves of tobacco and carrot and in cannabis plants (PMID:6991645 ). Pyrrolidine is present in bread, milk, cheese, carrots, celery stalks, beer, spirits, coffee, caviar, and fatty fish. Pyrrolidine is a flavouring agent added in trace amounts to chewing gum, soft candy, and non-alcoholic beverages (RoutledgeHandbooks-9781439847503-chapter3.pdf). Pyrrolidine is widely distributed in foodstuffs in trace amounts, presumably as a bacterial decarboxylation product of proline Pyrrolidine is a metabolite of the gram-negative bacterium, Xenorhabdus (PMID: 19598185 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-AzacyclopentaneChEBI
AzacyclopentaneChEBI
AzolidineChEBI
ButylenimineChEBI
PerhydropyrroleChEBI
ProlamineChEBI
TetrahydropyrroleChEBI
TetramethylenimineChEBI
FEMA 3523HMDB
Pyrrolidine hydrochlorideHMDB
Chemical FormulaC4H9N
Average Molecular Weight71.12
Monoisotopic Molecular Weight71.0735
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
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassNot Available
Direct ParentPyrrolidines
Alternative Parents
Substituents
  • Pyrrolidine
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

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Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-63 °CNot Available
Boiling Point87 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPyrrolidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fu-9000000000-0159c6ac6a2707c890fbSpectrum
Predicted GC-MSPyrrolidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-00di-9000000000-b47872c22f260420fe4f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-00di-9000000000-6703dc4e588e5b605dd22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-00di-9000000000-1200244cbd952b0ff0e42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-00di-9000000000-3e962c9c87606d1d4fb42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-00di-9000000000-7aa207733141b620c6122020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-00di-9000000000-cc43ed19d9780ad479072020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-00di-9000000000-6d604c6cb07d4b319fa72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-00di-9000000000-201fcadb62ee720ec9e32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-00dl-9000000000-2efe28538fd9387c11052020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-006x-9000000000-fe10abd985612deaee7b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-0006-9000000000-cc3a8f0b0eb43d64f2a42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 45V, positivesplash10-0006-9000000000-e5549871379e536221f32020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-50250fbde117c345f1552016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-9a9bb68d33a6b556f7532016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9000000000-4840aa812595ffd33b172016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-dc4555408f7b7029c1ec2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-d7dcf188af1b7f8ac9b42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udl-9000000000-0e5b8e3fe42b29779d062016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-ae345dd26f637d1e1b0e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-98df592a95307772b96d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-f474b8622abebc0362222021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-0c177e779175985339232021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kf-9000000000-12476e11ce42857385902021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-554f1bc121aa553aac432021-09-23View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0031641
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB007401
KNApSAcK IDC00002037
Chemspider ID29008
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPyrrolidine
METLIN IDNot Available
PubChem Compound31268
PDB IDNot Available
ChEBI ID33135
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. 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 ]