Piperidine (YMDB01338)

Identification

YMDB ID

YMDB01338

Name

Piperidine

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Piperidine (Azinane after the Hantzsch–Widman nomenclature) is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene units and one nitrogen atom. It is a colorless fuming liquid with an odor described as ammoniacal, pepper-like; the name comes from the genus name Piper, which is the Latin word for pepper. Piperidine is a widely used building block and chemical reagent in the synthesis of organic compounds, including pharmaceuticals. [Wikipedia]

Structure

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

Synonyms

.alpha.-Pipecolinic acid
(.+/-.)-2-Piperidinecarboxylic acid
()-Piperidine-2-carboxylic acid
(+/-)-2-Piperidinecarboxylate
(+/-)-2-Piperidinecarboxylic acid
(+/-)-Pipecolate
(+/-)-Pipecolic acid
(+/-)-Pipecolinate
(+/-)-Pipecolinic acid
(RS)-2-Piperidinecarboxylate
(RS)-2-Piperidinecarboxylic acid
2-Carboxypiperidine
2-Pipecolinic acid
2-Piperidinecarboxylate
2-piperidinecarboxylic acid
2-Piperidinylcarboxylic acid
a-Pipecolinate
a-Pipecolinic acid
acide pipecolique
acide piperidine-carboxylique-2
alpha-Pipecolinate
alpha-Pipecolinic acid
Azacyclohexane
Cyclopentimine
Cypentil
Dihydrobaikiane
DL-2-Piperidinecarboxylate
DL-2-Piperidinecarboxylic acid
DL-Homoproline
DL-Pipecolate
DL-Pipecolic acid
DL-Pipecolinate
DL-Pipecolinic acid
Hexahydro-2-picolinate
Hexahydro-2-picolinic acid
Hexahydropicolinate
Hexahydropicolinic acid
Hexahydropyridine
Hexazane
Homoproline
L-Pipecolate
Pentamethyleneamine
Pentamethyleneimine
Pentamethylenimine
Perhydropyridine
pipecolate
pipecolic acid
Pipecolic acid free base
Pipecolinate
pipecolinic acid
Piperidin
piperidine-2-carboxylic acid
Piperolinate
Piperolinic acid
Pyridine, hexahydro-
Azinane
pip
FEMA 2908
hexahydro-Pyridine
Piperidine ON rasta resin

CAS number

535-75-1

Weight

Average: 85.1475
Monoisotopic: 85.089149357

InChI Key

NQRYJNQNLNOLGT-UHFFFAOYSA-N

InChI

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

IUPAC Name

piperidine

Traditional IUPAC Name

piperidine

Chemical Formula

C₅H₁₁N

SMILES

C1CCNCC1

Chemical Taxonomy

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 )

Physical Properties

State

Solid

Charge

Melting point

264 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	-2.31 [TSAI,RS ET AL. (1991)]	PhysProp

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

extracellular

Organoleptic Properties

Flavour/Odour	Source
Animal	FDB012644
Bitter	FDB012644
Floral	FDB012644
Heavy	FDB012644
Sweet	FDB012644

SMPDB Pathways

Not Available

KEGG Pathways

Lysine degradation

ec00310

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0543-9000000000-6b1887859e5474352d6e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-053u-9000000000-507e3f9eabf271f642f3	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0563-9000000000-c08d3d67e81c397678d2	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0543-9000000000-6b1887859e5474352d6e	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-053u-9000000000-507e3f9eabf271f642f3	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0563-9000000000-c08d3d67e81c397678d2	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052u-9000000000-95f068cd42017a2e7446	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-9000000000-a76c8bf8d69f5f3e831a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-9000000000-fe1ffe6a62bbbfa35a46	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-9000000000-c57e3de57c466c728f49	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000f-9000000000-7936721ae1a323f2cd83	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000f-9000000000-6bcb90141de97851b0ce	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-9000000000-155786c0621c522e75a7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-014i-9000000000-646cb2a227fa351da3dc	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-014i-9000000000-32222dc7a0d132edf443	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-014i-9000000000-646cb2a227fa351da3dc	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-014i-9000000000-071a5573608ae27993d5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-014i-9000000000-80fe3a58dda39ff48e6f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-000i-9000000000-544d5b027d322e9b7a06	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-000i-9000000000-544d5b027d322e9b7a06	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-000i-9000000000-544d5b027d322e9b7a06	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-000i-9000000000-1a5edb15988820bf46f7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-000i-9000000000-79404da79119ad6ba660	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-000i-9000000000-f83e1ccbb9745637eb97	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-000i-9000000000-348e151611d5b46f3a33	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-000i-9000000000-8c4547384f2bc29d797b	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-bd6d487d25b0e623403e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9000000000-d9b236846b0611684014	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ku-9000000000-508b10b77d98c3915247	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9000000000-b616957223f2d18551fd	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-a2e05ca3b5d63ce6a366	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-015c-9000000000-49c805d2b27473cc8f88	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-053u-9000000000-9b296a6ad56d186eee6f	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Tsakiris, A., Koutinas, A. A., Psarianos, C., Kourkoutas, Y., Bekatorou, A. (2010). "A new process for wine production by penetration of yeast in uncrushed frozen grapes." Appl Biochem Biotechnol 162:1109-1121.20151225

Synthesis Reference:

Asher, Vikram; Becu, Christian; Anteunis, Marc J. O.; Callens, Roland. New synthesis of pipecolic acid and analogs. Tetrahedron Letters (1981), 22(2), 141-4.

External Links:

Resource	Link
CHEBI ID	17964
HMDB ID	HMDB00070
Pubchem Compound ID	8082
Kegg ID	C00408
ChemSpider ID	7791
FOODB ID	FDB012644
Wikipedia	Piperidine
BioCyc ID	5-HYDROXY-PIPECOLATE

Structure for #<Compound:0xa8589758>