Showing Compound Piperidine (FDB012644)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:17 UTC

Update date

2020-09-17 15:30:15 UTC

Primary ID

FDB012644

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Piperidine

Description

Piperidine, named after the genus Piper, which is Latin for pepper, has the molecular formula (CH2)5NH. It is a heterocyclic amine which consists of a six-membered ring containing five methylene units and one nitrogen atom. Piperidine is a strong basic compound. It is a colorless fuming liquid with an ammoniacal and pepper-like odor. It is found in black pepper fruit, oil and seed (Piper nigrum), barley seeds, celery plant, bell pepper and tobacco ( http://www.thegoodscentscompany.com/data/rw1009201.html#tooccur). Piperidine was obtained from the plants Psilocaulon absimile (Aizoaceae) and in Petrosimonia monandra ( https://en.wikipedia.org/wiki/Piperidine#cite_note-17). Piperidine is metabolized by microbes and is potentially used as an anti-bacterial agent controlling bacterial populations within rhizomes (http//doi.org/10.1101/499731). Piperidine is a widely used building block and chemical reagent in the synthesis of organic compounds, including pharmaceuticals such as vasodilators and antipsychotic medications (PMID: 25255204). Piperidine is a widely used secondary amine and used to convert ketones to enamines. Enamines derived from piperidine can be used in the Stork enamine alkylation reaction. Piperidine is used as a solvent and as a base. The same is true for certain derivatives: N-formylpiperidine is a polar aprotic solvent with better hydrocarbon solubility than other amide solvents, and 2,2,6,6-tetramethylpiperidine is highly sterically hindered base, useful because of its low nucleophilicity and high solubility in organic solvents.

CAS Number

110-89-4

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Azacyclohexane	ChEBI
Azinane	ChEBI
Cyclopentimine	ChEBI
Cypentil	ChEBI
Hexahydropyridine	ChEBI
Hexazane	ChEBI
Pentamethyleneamine	ChEBI
Pentamethyleneimine	ChEBI
Pentamethylenimine	ChEBI
Perhydropyridine	ChEBI
pip	ChEBI
Piperidin	ChEBI
FEMA 2908	HMDB
hexahydro-Pyridine	HMDB
Piperidine ON rasta resin	HMDB
PIP	biospider
Piperidine [UN2401] [Corrosive]	biospider
Piperidine on rasta resin	biospider
Pyridine, hexahydro-	biospider

Predicted Properties

Property	Value	Source
Water Solubility	124 g/L	ALOGPS
logP	0.97	ALOGPS
logP	0.66	ChemAxon
logS	0.16	ALOGPS
pKa (Strongest Basic)	10.4	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	26.84 m³·mol⁻¹	ChemAxon
Polarizability	10.43 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

C5H11N

IUPAC name

piperidine

InChI Identifier

InChI=1S/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2

InChI Key

NQRYJNQNLNOLGT-UHFFFAOYSA-N

Isomeric SMILES

C1CCNCC1

Average Molecular Weight

85.1475

Monoisotopic Molecular Weight

85.089149357

Classification

Description

Belongs to the class of organic compounds known as piperidines. Piperidines are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Not Available

Direct Parent

Piperidines

Alternative Parents

Substituents

Piperidine
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

piperidines (CHEBI:18049 )
secondary amine (CHEBI:18049 )
azacycloalkane (CHEBI:18049 )
saturated organic heteromonocyclic parent (CHEBI:18049 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Microbe

Plant:

Biological location:

Biofluid and excreta:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition:

Flavoring agent

Laboratory chemical

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 70.53%; H 13.02%; N 16.45%	DFC
Melting Point	Mp -9°	DFC
Boiling Point	Bp20 17.7°	DFC
Experimental Water Solubility	1000 mg/mL at 20 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	0.84	HANSCH,C ET AL. (1995)
Experimental pKa	pKa 11.12 (25°)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d204 0.86	DFC
Refractive Index	n20D 1.4534	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-053u-9000000000-9b296a6ad56d186eee6f	2015-03-01	View Spectrum
GC-MS	Piperidine, non-derivatized, GC-MS Spectrum	splash10-0543-9000000000-6b1887859e5474352d6e	Spectrum
GC-MS	Piperidine, non-derivatized, GC-MS Spectrum	splash10-053u-9000000000-507e3f9eabf271f642f3	Spectrum
GC-MS	Piperidine, non-derivatized, GC-MS Spectrum	splash10-0563-9000000000-c08d3d67e81c397678d2	Spectrum
GC-MS	Piperidine, non-derivatized, GC-MS Spectrum	splash10-0543-9000000000-6b1887859e5474352d6e	Spectrum
GC-MS	Piperidine, non-derivatized, GC-MS Spectrum	splash10-053u-9000000000-507e3f9eabf271f642f3	Spectrum
GC-MS	Piperidine, non-derivatized, GC-MS Spectrum	splash10-0563-9000000000-c08d3d67e81c397678d2	Spectrum
Predicted GC-MS	Piperidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052u-9000000000-95f068cd42017a2e7446	Spectrum
Predicted GC-MS	Piperidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Piperidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-9000000000-a76c8bf8d69f5f3e831a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-9000000000-fe1ffe6a62bbbfa35a46	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-9000000000-c57e3de57c466c728f49	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000f-9000000000-7936721ae1a323f2cd83	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000f-9000000000-6bcb90141de97851b0ce	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-9000000000-155786c0621c522e75a7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-014i-9000000000-646cb2a227fa351da3dc	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-014i-9000000000-32222dc7a0d132edf443	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-014i-9000000000-646cb2a227fa351da3dc	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-014i-9000000000-071a5573608ae27993d5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-014i-9000000000-80fe3a58dda39ff48e6f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-000i-9000000000-544d5b027d322e9b7a06	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-000i-9000000000-544d5b027d322e9b7a06	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-000i-9000000000-544d5b027d322e9b7a06	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-000i-9000000000-1a5edb15988820bf46f7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-000i-9000000000-79404da79119ad6ba660	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-000i-9000000000-f83e1ccbb9745637eb97	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-000i-9000000000-348e151611d5b46f3a33	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-000i-9000000000-8c4547384f2bc29d797b	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-bd6d487d25b0e623403e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9000000000-d9b236846b0611684014	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ku-9000000000-508b10b77d98c3915247	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9000000000-b616957223f2d18551fd	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-a2e05ca3b5d63ce6a366	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-015c-9000000000-49c805d2b27473cc8f88	2016-08-03	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

18049

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB34301

CRC / DFC (Dictionary of Food Compounds) ID

HJM94-U:HJM94-U

EAFUS ID

3053

Dr. Duke ID

PIPERIDINE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

PIP

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1009201

SuperScent ID

8082

Wikipedia ID

Piperidine

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

Descriptor	ID	Definition	Reference
Anti enzymatic		An agent that inhibits or counteracts enzyme activity, playing a crucial biological role in regulating metabolic pathways. Therapeutically, it has applications in managing enzyme-related disorders. Key medical uses include treating conditions like cancer, inflammatory diseases, and genetic disorders by blocking specific enzyme actions.	DUKE
Central nervous system depressant	35470	An agent that slows brain activity, reducing anxiety, stress, and excitability. Therapeutically, it's used to manage insomnia, seizures, and anxiety disorders, promoting relaxation and sedation. Key medical uses include treating insomnia, epilepsy, and panic disorders, as well as inducing anesthesia.	DUKE
Diaphoretic		An agent that induces perspiration, playing a biological role in thermoregulation. Therapeutically, it's used to treat fever, detoxify, and relieve congestion. Key medical uses include managing hyperthermia, aiding in toxin removal, and alleviating symptoms of colds and flu.	DUKE
Name	48318	flavor	DUKE
Hepatotropic		An agent with a special affinity for the liver, influencing its function and regeneration. It plays a biological role in liver repair and detoxification. Therapeutically, hepatotropics are used to treat liver diseases, such as hepatitis and cirrhosis, and have applications in managing liver cancer and promoting liver health.	DUKE
Insectifuge	24852	A substance that repels insects, playing a biological role in plant defense. Therapeutically, it has applications in preventing insect-borne diseases. Key medical uses include topical repellents for malaria, dengue fever, and other vector-borne illnesses, reducing the risk of transmission.	DUKE
Perfumery	48318	The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Spinoconvulsant		An agent that induces convulsions and/or epileptic seizures by affecting spinal cord nerves, with no established therapeutic applications due to its harmful effects, but used in research to study seizure mechanisms and spinal cord function.	DUKE
Urate-solvent		An agent that dissolves uric acid, aiding in its removal. It plays a biological role in reducing uric acid levels, with therapeutic applications in managing gout and kidney stones, and key medical uses in treating hyperuricemia and preventing uric acid buildup.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
animal	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
heavy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter	Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755