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Record Information
Version4.0
Creation Date2012-09-11 19:06:26 UTC
Update Date2017-09-27 08:30:20 UTC
HMDB IDHMDB0034301
Secondary Accession Numbers
  • HMDB34301
Metabolite Identification
Common NamePiperidine
DescriptionPiperidine is found in barley. Piperidine is present in black pepper (Piper nigrum). Piperidine is a flavouring agent 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. Piperidine is a widely used secondary amine. It is widely 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
Structure
Thumb
Synonyms
ValueSource
AzacyclohexaneChEBI
AzinaneChEBI
CyclopentimineChEBI
HexahydropyridineChEBI
PentamethyleneamineChEBI
PentamethyleneimineChEBI
PentamethylenimineChEBI
pipChEBI
CypentilHMDB
FEMA 2908HMDB
hexahydro-PyridineHMDB
HexazaneHMDB
PerhydropyridineHMDB
PiperidinHMDB
Piperidine ON rasta resinHMDB
Chemical FormulaC5H11N
Average Molecular Weight85.1475
Monoisotopic Molecular Weight85.089149357
IUPAC Namepiperidine
Traditional Namepiperidine
CAS Registry Number110-89-4
SMILES
C1CCNCC1
InChI Identifier
InChI=1S/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2
InChI KeyNQRYJNQNLNOLGT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as piperidines. These are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassPiperidines
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
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Role

Biological role:

Industrial application:

  Food and nutrition:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-9 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 20 °CNot Available
LogP0.84Not Available
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-Bsplash10-0543-9000000000-6b1887859e5474352d6eView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-053u-9000000000-507e3f9eabf271f642f3View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0563-9000000000-c08d3d67e81c397678d2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-9000000000-a76c8bf8d69f5f3e831aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-9000000000-fe1ffe6a62bbbfa35a46View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-9000000000-c57e3de57c466c728f49View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000f-9000000000-7936721ae1a323f2cd83View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000f-9000000000-6bcb90141de97851b0ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-9000000000-155786c0621c522e75a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-9000000000-646cb2a227fa351da3dcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-9000000000-32222dc7a0d132edf443View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-9000000000-646cb2a227fa351da3dcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-9000000000-071a5573608ae27993d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-9000000000-80fe3a58dda39ff48e6fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-544d5b027d322e9b7a06View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-544d5b027d322e9b7a06View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-544d5b027d322e9b7a06View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-1a5edb15988820bf46f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-79404da79119ad6ba660View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-f83e1ccbb9745637eb97View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-348e151611d5b46f3a33View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-000i-9000000000-8c4547384f2bc29d797bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-bd6d487d25b0e623403eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9000000000-d9b236846b0611684014View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ku-9000000000-508b10b77d98c3915247View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableView in JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-053u-9000000000-9b296a6ad56d186eee6fView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)BothNormal details
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
SalivaDetected but not Quantified Adult (>18 years old)BothOral cancer details
SalivaDetected but not Quantified Adult (>18 years old)FemaleBreast cancer details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedPancreatic cancer details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedPeriodontal diseases details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012644
KNApSAcK IDNot Available
Chemspider ID7791
KEGG Compound IDC01746
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPiperidine
METLIN IDNot Available
PubChem Compound8082
PDB IDPIP
ChEBI ID18049
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. De Marco A, De Candia M, Carotti A, Cellamare S, De Candia E, Altomare C: Lipophilicity-related inhibition of blood platelet aggregation by nipecotic acid anilides. Eur J Pharm Sci. 2004 Jun;22(2-3):153-64. [PubMed:15158900 ]
  2. Dembitsky VM: Astonishing diversity of natural surfactants: 6. Biologically active marine and terrestrial alkaloid glycosides. Lipids. 2005 Nov;40(11):1081-105. [PubMed:16459921 ]
  3. Aisaka K, Hattori Y, Ishihara T, Morita M, Kase Y, Miyata T: The effects of piperidine and its related substances on blood vessels. Jpn J Pharmacol. 1985 Apr;37(4):345-53. [PubMed:4010086 ]
  4. Patel K, Chen Y, Dennehy K, Blau J, Connors S, Mendonca M, Tarpey M, Krishna M, Mitchell JB, Welch WJ, Wilcox CS: Acute antihypertensive action of nitroxides in the spontaneously hypertensive rat. Am J Physiol Regul Integr Comp Physiol. 2006 Jan;290(1):R37-43. Epub 2005 Sep 22. [PubMed:16179488 ]
  5. Nishi K, Iwasaki K, Kase Y: Actions of piperidine and dimethylphenylpiperazinium (DMPP) on afferent discharges of the cat's carotid body. Eur J Pharmacol. 1979 Feb 15;54(1-2):141-52. [PubMed:421736 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .