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Identification
YMDB IDYMDB01338
NamePiperidine
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPiperidine (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
Thumb
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 number535-75-1
WeightAverage: 85.1475
Monoisotopic: 85.089149357
InChI KeyNQRYJNQNLNOLGT-UHFFFAOYSA-N
InChIInChI=1S/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2
IUPAC Namepiperidine
Traditional IUPAC Namepiperidine
Chemical FormulaC5H11N
SMILESC1CCNCC1
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassNot Available
Direct ParentPiperidines
Alternative Parents
Substituents
  • Piperidine
  • 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
Physical Properties
StateSolid
Charge0
Melting point264 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogP-2.31 [TSAI,RS ET AL. (1991)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility124 g/LALOGPS
logP0.97ALOGPS
logP0.66ChemAxon
logS0.16ALOGPS
pKa (Strongest Basic)10.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.84 m³·mol⁻¹ChemAxon
Polarizability10.43 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
Organoleptic Properties
Flavour/OdourSource
AnimalFDB012644
BitterFDB012644
FloralFDB012644
HeavyFDB012644
SweetFDB012644
SMPDB PathwaysNot Available
KEGG Pathways
Lysine degradationec00310 Map00310
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0543-9000000000-6b1887859e5474352d6eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-053u-9000000000-507e3f9eabf271f642f3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0563-9000000000-c08d3d67e81c397678d2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0543-9000000000-6b1887859e5474352d6eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-053u-9000000000-507e3f9eabf271f642f3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0563-9000000000-c08d3d67e81c397678d2JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052u-9000000000-95f068cd42017a2e7446JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-9000000000-a76c8bf8d69f5f3e831aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-9000000000-fe1ffe6a62bbbfa35a46JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-9000000000-c57e3de57c466c728f49JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000f-9000000000-7936721ae1a323f2cd83JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000f-9000000000-6bcb90141de97851b0ceJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-9000000000-155786c0621c522e75a7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-9000000000-646cb2a227fa351da3dcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-9000000000-32222dc7a0d132edf443JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-9000000000-646cb2a227fa351da3dcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-9000000000-071a5573608ae27993d5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-9000000000-80fe3a58dda39ff48e6fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-544d5b027d322e9b7a06JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-544d5b027d322e9b7a06JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-544d5b027d322e9b7a06JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-1a5edb15988820bf46f7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-79404da79119ad6ba660JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-f83e1ccbb9745637eb97JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-348e151611d5b46f3a33JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-8c4547384f2bc29d797bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-bd6d487d25b0e623403eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9000000000-d9b236846b0611684014JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ku-9000000000-508b10b77d98c3915247JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-b616957223f2d18551fdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-a2e05ca3b5d63ce6a366JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-015c-9000000000-49c805d2b27473cc8f88JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-053u-9000000000-9b296a6ad56d186eee6fJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
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:
ResourceLink
CHEBI ID17964
HMDB IDHMDB00070
Pubchem Compound ID8082
Kegg IDC00408
ChemSpider ID7791
FOODB IDFDB012644
WikipediaPiperidine
BioCyc ID5-HYDROXY-PIPECOLATE