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Record Information
Version3.6
Creation Date2006-08-24 12:19:01 UTC
Update Date2016-02-11 01:06:51 UTC
HMDB IDHMDB04814
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Heptanone
DescriptionIs a volatile organic ketone found in almost all urine samples of normal individuals. (PMID 15996539 ). It has been hypothesized that arises from in vivo beta-oxidation of 2-ethylhexanoic acid (EHA) from plasticizers, similar to formation of 3-heptanone from valproic acid. (PMID 11282094 ).
Structure
Thumb
Synonyms
ValueSource
4-OxoheptaneHMDB
ButyroneHMDB
Di-N-propyl ketoneHMDB
Dipropyl ketoneHMDB
Propyl ketoneHMDB
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 KeyInChIKey=HCFAJYNVAYBARA-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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 ClassOrganooxygen compounds
ClassCarbonyl compounds
Sub ClassKetones
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
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 mg/mLALOGPS
logP2.06ALOGPS
logP2.4ChemAxon
logS-1.4ALOGPS
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.65 m3·mol-1ChemAxon
Polarizability14.21 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-9000000000-a9c1716125865fd1e6f4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-663608c3582f62ba8da0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004l-9000000000-4cc0010d9a1f24b75279View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0006-9000000000-87f6dc51de91b8902d69View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-006x-9000000000-781083206e97b4ff2795View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.030 (0.01-0.050) uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableNewborn (0-30 days old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>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 QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.070 (0.040-0.090) uMAdult (>18 years old)Both
Kidney disease
details
FecesDetected but not QuantifiedNot ApplicableChildren (1-13 years old)Not Specified
Treated celiac disease
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Clostridium difficile infection
details
UrineDetected but not QuantifiedNot ApplicableAdult (>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
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. [10431355 ]
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. [914932 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008059
KNApSAcK IDC00035501
Chemspider ID28986
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04814
Metagene LinkHMDB04814
METLIN ID7078
PubChem Compound31246
PDB IDNot Available
ChEBI 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. [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. [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. [11282094 ]