Showing Compound Prolamine (FDB007401)

Record Information

Version

1.0

Creation date

2010-04-08 22:07:35 UTC

Update date

2020-09-17 15:30:26 UTC

Primary ID

FDB007401

Secondary Accession Numbers

FDB008290

Chemical Information

FooDB Name

Prolamine

Description

Pyrrolidine, 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 ( http://www.thegoodscentscompany.com/data/rw1009391.html). Pyrrolidine is found naturally in the leaves of tobacco and carrot. 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).

CAS Number

123-75-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

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

Predicted Properties

Property	Value	Source
Water Solubility	291 g/L	ALOGPS
logP	0.16	ALOGPS
logP	0.21	ChemAxon
logS	0.61	ALOGPS
pKa (Strongest Basic)	11.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	12.03 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	22.23 m³·mol⁻¹	ChemAxon
Polarizability	8.58 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

Chemical Formula

C4H9N

IUPAC name

pyrrolidine

InChI Identifier

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

InChI Key

RWRDLPDLKQPQOW-UHFFFAOYSA-N

Isomeric SMILES

C1CCNC1

Average Molecular Weight

71.121

Monoisotopic Molecular Weight

71.073499293

Classification

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Microbe:

Xenorhabdus:

Xenorhabdus nematophila

Plant:

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition:

Flavoring agent

Pharmaceutical industry:

Antineoplastic agent:

Antitumor

Biological role:

Free radical scavenger

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Prolamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00fu-9000000000-0159c6ac6a2707c890fb	Spectrum
Predicted GC-MS	Prolamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-00di-9000000000-b47872c22f260420fe4f	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-00di-9000000000-6703dc4e588e5b605dd2	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-00di-9000000000-1200244cbd952b0ff0e4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-00di-9000000000-3e962c9c87606d1d4fb4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-00di-9000000000-7aa207733141b620c612	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-00di-9000000000-cc43ed19d9780ad47907	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-00di-9000000000-6d604c6cb07d4b319fa7	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-00di-9000000000-201fcadb62ee720ec9e3	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 33V, positive	splash10-00dl-9000000000-2efe28538fd9387c1105	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 35V, positive	splash10-006x-9000000000-fe10abd985612deaee7b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-0006-9000000000-cc3a8f0b0eb43d64f2a4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 45V, positive	splash10-0006-9000000000-e5549871379e536221f3	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-50250fbde117c345f155	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-9a9bb68d33a6b556f753	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ab9-9000000000-4840aa812595ffd33b17	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-dc4555408f7b7029c1ec	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-d7dcf188af1b7f8ac9b4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udl-9000000000-0e5b8e3fe42b29779d06	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-ae345dd26f637d1e1b0e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-98df592a95307772b96d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-f474b8622abebc036222	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-0c177e77917598533923	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kf-9000000000-12476e11ce4285738590	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-554f1bc121aa553aac43	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

PROLAMINE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Prolamin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
alkaline	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).