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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 19:02:21 UTC
Update Date2019-07-23 06:15:32 UTC
HMDB IDHMDB0034235
Secondary Accession Numbers
  • HMDB34235
Metabolite Identification
Common Name2-Pentanone
Description2-Pentanone, also known as ethyl acetone or fema 2842, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, 2-pentanone is considered to be an oxygenated hydrocarbon lipid molecule. 2-Pentanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Pentanone is a sweet, alcohol, and banana tasting compound. Outside of the human body, 2-Pentanone is found, on average, in the highest concentration within milk (cow). 2-Pentanone has also been detected, but not quantified in, several different foods, such as fats and oils, corns, apples, evergreen blackberries, and fruits. This could make 2-pentanone a potential biomarker for the consumption of these foods. 2-Pentanone, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, nonalcoholic fatty liver disease, and crohn's disease; 2-pentanone has also been linked to the inborn metabolic disorder celiac disease. A pentanone carrying an oxo substituent at position 2.
Structure
Data?1563862532
Synonyms
ValueSource
Methyl propyl ketoneChEBI
Ethyl acetoneHMDB
EthylacetoneHMDB
FEMA 2842HMDB
Methyl N-propyl ketoneHMDB
Methyl-N-propyl ketoneHMDB
Methyl-propyl-cetoneHMDB
Methylpropyl ketoneHMDB
MetylopropyloketonHMDB
MPKHMDB
N-C3H7COCH3HMDB
N-Propyl methyl ketoneHMDB
PENTAN-2-oneHMDB
PentanoneHMDB
Pentanone-2HMDB
Propyl methyl ketoneHMDB
2-PentanoneChEBI
Chemical FormulaC5H10O
Average Molecular Weight86.1323
Monoisotopic Molecular Weight86.073164942
IUPAC Namepentan-2-one
Traditional Name2-pentanone
CAS Registry Number107-87-9
SMILES
CCCC(C)=O
InChI Identifier
InChI=1S/C5H10O/c1-3-4-5(2)6/h3-4H2,1-2H3
InChI KeyXNLICIUVMPYHGG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-76.9 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility43 mg/mL at 25 °CNot Available
LogP0.91Not Available
Predicted Properties
PropertyValueSource
Water Solubility29.5 g/LALOGPS
logP0.87ALOGPS
logP1.25ChemAxon
logS-0.47ALOGPS
pKa (Strongest Acidic)19.65ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.42 m³·mol⁻¹ChemAxon
Polarizability10.26 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-cd084d7fb390ed239f79Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-a8e31a9aba1a3bc1fe5aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-9d6ab400df7dd4c12a37Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-b4ba5ddb582a624253c0Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-cd084d7fb390ed239f79Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-a8e31a9aba1a3bc1fe5aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-9d6ab400df7dd4c12a37Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-b4ba5ddb582a624253c0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-88e909b639cb48d4866dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-9000000000-1c38ed487f1bcb4aeee8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-9000000000-3f64843cdd14d5d31f06Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-c73f068d1777d33c5140Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-0c79c8c6b9ee4aa2a2cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-dbac0805a7ae1a0fc0e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-996ef95b676dd2597c22Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-801a958c8ff6cf1a07acSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified8750.105 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected and Quantified13243.193 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected and Quantified13359.293 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Not Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Newborn (0-30 days old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Children (1-13 years old)Not Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
Ulcerative Colitis
details
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not Quantified Children (1-13 years old)Not Specified
Treated celiac disease
details
FecesDetected but not Quantified Adult (>18 years old)BothCrohns disease details
FecesDetected but not Quantified Adult (>18 years old)BothUlcerative colitis details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  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 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Crohn's disease
  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
FooDB IDFDB012547
KNApSAcK IDNot Available
Chemspider ID7607
KEGG Compound IDC01949
BioCyc IDPENTAN-2-ONE
BiGG IDNot Available
Wikipedia LinkPentan-2-one
METLIN IDNot Available
PubChem Compound7895
PDB IDPNH
ChEBI ID16472
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .