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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 19:06:26 UTC
Update Date2023-02-21 17:24:09 UTC
HMDB IDHMDB0034301
Secondary Accession Numbers
  • HMDB34301
Metabolite Identification
Common NamePiperidine
DescriptionPiperidine 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. 
Structure
Data?1677000249
Synonyms
ValueSource
AzacyclohexaneChEBI
AzinaneChEBI
CyclopentimineChEBI
CypentilChEBI
HexahydropyridineChEBI
HexazaneChEBI
PentamethyleneamineChEBI
PentamethyleneimineChEBI
PentamethylenimineChEBI
PerhydropyridineChEBI
pipChEBI
PiperidinChEBI
FEMA 2908HMDB
hexahydro-PyridineHMDB
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
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
Ontology
Not AvailableNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-9 °CNot Available
Boiling Point106.00 to 107.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000 mg/mL at 20 °CNot Available
LogP0.84Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+115.06531661259
DarkChem[M-H]-109.22731661259
DeepCCS[M+H]+123.9330932474
DeepCCS[M-H]-122.030932474
DeepCCS[M-2H]-157.36830932474
DeepCCS[M+Na]+131.8830932474
AllCCS[M+H]+115.832859911
AllCCS[M+H-H2O]+110.532859911
AllCCS[M+NH4]+120.732859911
AllCCS[M+Na]+122.132859911
AllCCS[M-H]-121.432859911
AllCCS[M+Na-2H]-125.132859911
AllCCS[M+HCOO]-129.332859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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 minutes32390414
Predicted by Siyang on May 30, 20228.1691 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20226.0 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid275.0 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid531.7 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid302.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid87.0 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid196.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid72.0 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid254.1 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid253.3 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)679.4 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid584.7 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid60.3 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid659.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid184.9 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid220.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate871.3 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA436.0 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water238.1 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PiperidineC1CCNCC11081.5Standard polar33892256
PiperidineC1CCNCC1766.3Standard non polar33892256
PiperidineC1CCNCC1739.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Piperidine,1TMS,isomer #1C[Si](C)(C)N1CCCCC1939.2Semi standard non polar33892256
Piperidine,1TMS,isomer #1C[Si](C)(C)N1CCCCC11006.9Standard non polar33892256
Piperidine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCCCC11177.6Semi standard non polar33892256
Piperidine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCCCC11218.8Standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Metastatic melanoma
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothOral cancer details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleBreast cancer details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedPancreatic cancer details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB IDFDB012644
KNApSAcK IDC00051876
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
MarkerDB IDNot Available
Good Scents IDrw1009201
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. 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 ]
  7. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .