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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2009-03-05 10:31:10 UTC
Update Date2018-05-20 18:56:40 UTC
HMDB IDHMDB0011749
Secondary Accession Numbers
  • HMDB11749
Metabolite Identification
Common Name2-Piperidinone
Description2-Piperidinone is a derivative of piperidine which is an organic compound. Piperidine 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.The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper the hot taste. This gave the compound its name.(Wikipedia).
Structure
Thumb
Synonyms
ValueSource
2-oxo-PiperidineChEBI
2-OxopiperidineChEBI
5-PentanolactamChEBI
alpha-PiperidoneChEBI
delta-ValerolactamChEBI
PiperidinoneChEBI
PiperidonChEBI
PiperidoneChEBI
Piperidone-2ChEBI
a-PiperidoneGenerator
α-piperidoneGenerator
δ-valerolactamGenerator
2-PiperidoneHMDB
5-amino-Lactam-pentanoateHMDB
5-amino-Lactam-pentanoic acidHMDB
ValerolactimHMDB
Piperidin-2-oneMeSH
Chemical FormulaC5H9NO
Average Molecular Weight99.1311
Monoisotopic Molecular Weight99.068413915
IUPAC Namepiperidin-2-one
Traditional Namedelta-valerolactam
CAS Registry Number675-20-7
SMILES
O=C1CCCCN1
InChI Identifier
InChI=1S/C5H9NO/c7-5-3-1-2-4-6-5/h1-4H2,(H,6,7)
InChI KeyXUWHAWMETYGRKB-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as piperidinones. These are compounds containing a piperidine ring which bears a ketone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassPiperidinones
Direct ParentPiperidinones
Alternative Parents
Substituents
  • Delta-lactam
  • Piperidinone
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point39.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility291 mg/mL at 25 °CNot Available
LogP-0.46HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility329 g/LALOGPS
logP-0.4ALOGPS
logP-0.14ChemAxon
logS0.52ALOGPS
pKa (Strongest Acidic)14.89ChemAxon
pKa (Strongest Basic)-0.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.86 m³·mol⁻¹ChemAxon
Polarizability10.66 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-B (Non-derivatized)splash10-0005-9000000000-1cbce19144683ef641e7View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udi-0900000000-685a07025543d28ecbacView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-a80b6b7cda436e704e7bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001l-9000000000-f37b3b1c1afb5c38f34eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ab9-1900000000-b82aaf6a400c4aeb324aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0005-9000000000-1cbce19144683ef641e7View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udi-0900000000-685a07025543d28ecbacView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-a80b6b7cda436e704e7bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001l-9000000000-f37b3b1c1afb5c38f34eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ab9-1900000000-b82aaf6a400c4aeb324aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05i4-9000000000-310ae81b8eba14881030View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-3900000000-fdf8e8b56fffa826f806View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-9700000000-532e46fb5d76aac2caa4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-7a15c8213ddfea3ef0b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-35fa6fd629b4d92ba945View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-75c5e190e25cb34f3e41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-3b18b4737fff701413e6View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Female
Ovarian cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)BothCrohns disease details
FecesDetected but not Quantified Adult (>18 years old)BothUlcerative colitis details
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Crohn's disease
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 ]
Crohn's disease
  1. Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]
  2. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Ovarian cancer
  1. Zhang T, Wu X, Yin M, Fan L, Zhang H, Zhao F, Zhang W, Ke C, Zhang G, Hou Y, Zhou X, Lou G, Li K: Discrimination between malignant and benign ovarian tumors by plasma metabolomic profiling using ultra performance liquid chromatography/mass spectrometry. Clin Chim Acta. 2012 May 18;413(9-10):861-8. doi: 10.1016/j.cca.2012.01.026. Epub 2012 Jan 30. [PubMed:22309680 ]
Ulcerative colitis
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028421
KNApSAcK IDNot Available
Chemspider ID12144
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Piperidinone
METLIN IDNot Available
PubChem Compound12665
PDB IDNot Available
ChEBI ID77761
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available