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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-24 12:19:01 UTC
Update Date2020-02-26 21:25:14 UTC
HMDB IDHMDB0004814
Secondary Accession Numbers
  • HMDB04814
Metabolite Identification
Common Name4-Heptanone
Description4-Heptanone, also known as dipropyl ketone or 4-oxoheptane, 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, 4-heptanone is considered to be an oxygenated hydrocarbon lipid molecule. 4-Heptanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Heptanone is a sweet, cheese, and cognac tasting compound. Outside of the human body,. 4-Heptanone, with regard to humans, has been found to be associated with several diseases such as kidney disease, perillyl alcohol administration for cancer treatment, pervasive developmental disorder not otherwise specified, and autism; 4-heptanone has also been linked to the inborn metabolic disorder celiac disease.
Structure
Data?1582752314
Synonyms
ValueSource
4-OxoheptaneChEBI
ButyroneChEBI
Di-N-propyl ketoneChEBI
Dipropyl ketoneChEBI
Heptan-4-oneChEBI
Propyl ketoneChEBI
4-HeptanoneMeSH
Chemical FormulaC7H14O
Average Molecular Weight114.1855
Monoisotopic Molecular Weight114.10446507
IUPAC Nameheptan-4-one
Traditional Namepropyl ketone
CAS Registry Number123-19-3
SMILES
CCCC(=O)CCC
InChI Identifier
InChI=1S/C7H14O/c1-3-5-7(8)6-4-2/h3-6H2,1-2H3
InChI KeyHCFAJYNVAYBARA-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
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-34 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.2 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.51 g/LALOGPS
logP2.06ALOGPS
logP2.4ChemAxon
logS-1.4ALOGPS
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.65 m³·mol⁻¹ChemAxon
Polarizability14.21 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)splash10-0006-9000000000-87f6dc51de91b8902d69Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9000000000-781083206e97b4ff2795Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-87f6dc51de91b8902d69Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-9000000000-781083206e97b4ff2795Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9000000000-352c1f3ffaaebea0bd8cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-9000000000-a9c1716125865fd1e6f4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-663608c3582f62ba8da0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004l-9000000000-4cc0010d9a1f24b75279Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-87f6dc51de91b8902d69Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-006x-9000000000-781083206e97b4ff2795Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-2900000000-41dd6684626dc1d7f93fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9700000000-9c9968ea76751b36c995Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-fbb146d20144a5fd3d72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-afc1c7d8a43500575816Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-3900000000-a84055bdd9536934452aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-26a02f7aee4cb6cfadecSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.030 (0.01-0.050) uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Children (1-13 years old)BothNormal details
FecesDetected but not Quantified Children (1-13 years old)Not Specified
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 Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.1 (0.015-0.6) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.070 (0.040-0.090) uMAdult (>18 years old)Both
Kidney disease
details
FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
FecesDetected but not Quantified Children (1-13 years old)Bothautism details
FecesDetected but not Quantified Children (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
FecesDetected but not Quantified Children (1-13 years old)Not Specified
Treated celiac disease
details
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
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
UrineDetected but not Quantified Adult (>18 years old)BothBreast cancer details
UrineDetected and Quantified0.1 (0.0097-0.56) umol/mmol creatinineAdult (>18 years old)BothDiabetes details
Associated Disorders and Diseases
Disease References
Kidney disease
  1. Liebich HM, Woll J: Volatile substances in blood serum: profile analysis and quantitative determination. J Chromatogr. 1977 Nov 11;142:505-16. [PubMed:914932 ]
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 ]
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Diabetes mellitus type 2
  1. Wahl HG, Hoffmann A, Luft D, Liebich HM: Analysis of volatile organic compounds in human urine by headspace gas chromatography-mass spectrometry with a multipurpose sampler. J Chromatogr A. 1999 Jun 25;847(1-2):117-25. [PubMed:10431355 ]
Perillyl alcohol administration for cancer treatment
  1. Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008059
KNApSAcK IDC00035501
Chemspider ID28986
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Heptanone
METLIN ID7078
PubChem Compound31246
PDB IDNot Available
ChEBI ID89484
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceWedekind, Edgar. Eienfilhrung in das Studium der organischen Chemie f.ovrddot.ur Studierende der Chemie, Medizin, Pharmazie, Naturwissenschaft, Forstwissenschaft u. s. w. 235 pp. CAN 20:19120 AN 1926:19120
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Wahl HG, Hoffmann A, Luft D, Liebich HM: Analysis of volatile organic compounds in human urine by headspace gas chromatography-mass spectrometry with a multipurpose sampler. J Chromatogr A. 1999 Jun 25;847(1-2):117-25. [PubMed:10431355 ]
  2. Statheropoulos M, Sianos E, Agapiou A, Georgiadou A, Pappa A, Tzamtzis N, Giotaki H, Papageorgiou C, Kolostoumbis D: Preliminary investigation of using volatile organic compounds from human expired air, blood and urine for locating entrapped people in earthquakes. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 5;822(1-2):112-7. [PubMed:15996539 ]
  3. Walker V, Mills GA: Urine 4-heptanone: a beta-oxidation product of 2-ethylhexanoic acid from plasticisers. Clin Chim Acta. 2001 Apr;306(1-2):51-61. [PubMed:11282094 ]