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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 19:06:26 UTC
Update Date2019-07-23 06:15:42 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. Piperidine has been found to be a microbial metabolite.
Structure
Data?1563862542
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 organic compounds 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.
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

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
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 | MoNA
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 | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9000000000-d9b236846b0611684014JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ku-9000000000-508b10b77d98c3915247JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-b616957223f2d18551fdJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-a2e05ca3b5d63ce6a366JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-015c-9000000000-49c805d2b27473cc8f88JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-053u-9000000000-9b296a6ad56d186eee6fJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)BothNormal details
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Metastatic melanoma
details
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 References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Metastatic melanoma
  1. Frankel AE, Coughlin LA, Kim J, Froehlich TW, Xie Y, Frenkel EP, Koh AY: Metagenomic Shotgun Sequencing and Unbiased Metabolomic Profiling Identify Specific Human Gut Microbiota and Metabolites Associated with Immune Checkpoint Therapy Efficacy in Melanoma Patients. Neoplasia. 2017 Oct;19(10):848-855. doi: 10.1016/j.neo.2017.08.004. Epub 2017 Sep 15. [PubMed:28923537 ]
Perillyl alcohol administration for cancer treatment
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Pancreatic cancer
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Periodontal disease
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012644
KNApSAcK IDNot Available
Chemspider ID7791
KEGG Compound IDC01746
BioCyc IDPIPERIDINE
BiGG IDNot Available
Wikipedia LinkPiperidine
METLIN IDNot Available
PubChem Compound8082
PDB IDPIP
ChEBI ID18049
Food Biomarker OntologyNot Available
VMH IDNot Available
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.. .