| Record Information | 
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| Version | 5.0 | 
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| Status | Detected but not Quantified | 
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| Creation Date | 2012-09-11 19:06:26 UTC | 
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| Update Date | 2023-02-21 17:24:09 UTC | 
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| HMDB ID | HMDB0034301 | 
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| Secondary Accession Numbers |  | 
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| Metabolite Identification | 
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| Common Name | Piperidine | 
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| Description | Piperidine 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. Piperdine is a member of the class of compounds known as azacycloalkane. An azacyloalkane is cyclohexane in which one of the carbons is replaced by a nitrogen. Piperdine is a naturally occurring metabolite in the human body. In particular, it is a metabolite of cadaverine, a polyamine found in the human intestine and other mammalian intestines (PMID: 6406679  ). Piperidine is considered to be a microbial metabolite. Piperdine can be isolated from a variety of natural sources or synthesized in the lab and exists as a colorless fuming liquid with an odor described as ammoniacal or pepper-like. The name piperdine comes from the genus name Piper, which is the Latin word for pepper. Piperidine is found in a number of plants including black pepper (Piper nigrum), celery plants, bell peppers and tobacco. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. In food, piperidine is a flavouring agent and it is also widely used as a building block and chemical reagent in the synthesis of organic compounds, including pharmaceuticals. As a liquid, piperidine is used as a solvent and as a base. | 
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| Structure | InChI=1S/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2 | 
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| Synonyms | | Value | Source | 
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 | 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 | 
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| Chemical Formula | C5H11N | 
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| Average Molecular Weight | 85.1475 | 
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| Monoisotopic Molecular Weight | 85.089149357 | 
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| IUPAC Name | piperidine | 
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| Traditional Name | piperidine | 
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| CAS Registry Number | 110-89-4 | 
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| SMILES | C1CCNCC1 | 
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| InChI Identifier | InChI=1S/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2 | 
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| InChI Key | NQRYJNQNLNOLGT-UHFFFAOYSA-N | 
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| Chemical Taxonomy | 
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| 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. | 
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| Kingdom | Organic compounds | 
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| Super Class | Organoheterocyclic compounds | 
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| Class | Piperidines | 
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| Sub Class | Not Available | 
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| Direct Parent | Piperidines | 
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| Alternative Parents |  | 
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| Substituents | PiperidineAzacycleSecondary amineSecondary aliphatic amineOrganic nitrogen compoundOrganopnictogen compoundHydrocarbon derivativeOrganonitrogen compoundAmineAliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds | 
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| External Descriptors |  | 
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| Ontology | 
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| Not Available | Not Available | 
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| Physical Properties | 
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| State | Liquid | 
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| Experimental Molecular Properties | | Property | Value | Reference | 
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 | Melting Point | -9 °C | Not Available |  | Boiling Point | 106.00 to  107.00 °C. @  760.00 mm Hg | The Good Scents Company Information System |  | Water Solubility | 1000 mg/mL at 20 °C | Not Available |  | LogP | 0.84 | Not Available | 
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| Experimental Chromatographic Properties | Not Available | 
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| Predicted Molecular Properties |  | 
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| Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Retention Times Underivatized| Chromatographic Method | Retention Time | Reference | 
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 | Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022. | 1.91 minutes | 32390414 |  | Predicted by Siyang on May 30, 2022 | 8.1691 minutes | 33406817 |  | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 6.0 minutes | 32390414 |  | AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid | 275.0 seconds | 40023050 |  | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 531.7 seconds | 40023050 |  | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 302.3 seconds | 40023050 |  | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 87.0 seconds | 40023050 |  | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 196.1 seconds | 40023050 |  | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 72.0 seconds | 40023050 |  | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 254.1 seconds | 40023050 |  | BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid | 253.3 seconds | 40023050 |  | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 679.4 seconds | 40023050 |  | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 584.7 seconds | 40023050 |  | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 60.3 seconds | 40023050 |  | UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid | 659.5 seconds | 40023050 |  | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 184.9 seconds | 40023050 |  | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 220.9 seconds | 40023050 |  | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 871.3 seconds | 40023050 |  | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 436.0 seconds | 40023050 |  | Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water | 238.1 seconds | 40023050 | 
 Predicted Kovats Retention IndicesUnderivatizedDerivatized | 
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| Spectra | 
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| Biological Properties | 
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| Cellular Locations |  | 
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| Biospecimen Locations |  | 
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| Tissue Locations | Not Available | 
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| Pathways |  | 
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| Normal Concentrations | 
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 | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal |  | details |  | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal |  | details |  | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal |  | details | 
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| Abnormal Concentrations | 
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 | Blood | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Cancer patients undergoing total body irradiation |  | details |  | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer |  | details |  | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Metastatic melanoma |  | details |  | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Oral cancer |  | details |  | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Female | Breast cancer |  | details |  | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Not Specified | Pancreatic cancer |  | details |  | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Not Specified | Periodontal diseases |  | details | 
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| Associated Disorders and Diseases | 
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| Disease References | | Colorectal cancer | 
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 | 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 | 
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 | 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 | 
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 | 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 | 
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 | 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 | 
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 | 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  ] 
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| Associated OMIM IDs |  | 
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| External Links | 
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| DrugBank ID | Not Available | 
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| Phenol Explorer Compound ID | Not Available | 
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| FooDB ID | FDB012644 | 
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| KNApSAcK ID | C00051876 | 
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| Chemspider ID | 7791 | 
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| KEGG Compound ID | C01746 | 
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| BioCyc ID | PIPERIDINE | 
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| BiGG ID | Not Available | 
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| Wikipedia Link | Piperidine | 
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| METLIN ID | Not Available | 
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| PubChem Compound | 8082 | 
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| PDB ID | PIP | 
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| ChEBI ID | 18049 | 
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| Food Biomarker Ontology | Not Available | 
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| VMH ID | Not Available | 
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| MarkerDB ID | Not Available | 
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| Good Scents ID | rw1009201 | 
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| References | 
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| Synthesis Reference | Not Available | 
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| Material Safety Data Sheet (MSDS) | Not Available | 
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| General References | 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  ] Dembitsky VM: Astonishing diversity of natural surfactants: 6. Biologically active marine and terrestrial alkaloid glycosides. Lipids. 2005 Nov;40(11):1081-105. [PubMed:16459921  ] 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  ] 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  ] 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  ] Nomura Y, Schmidt-Glenewinkel T, Giacobini E, Ortiz J: Metabolism of cadaverine and pipecolic acid in brain and other organs of the mouse. J Neurosci Res. 1983;9(3):279-89. doi: 10.1002/jnr.490090305. [PubMed:6406679  ]  (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. . 
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