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Showing metabocard for 2-Oxohexane (HMDB0005842)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-04-12 15:37:12 UTC
Update Date2020-02-26 21:26:07 UTC
HMDB IDHMDB0005842
Secondary Accession Numbers
  • HMDB05842
Metabolite Identification
Common Name2-Oxohexane
Description2-Oxohexane, also known as hexan-2-one or MNBK, 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-oxohexane is considered to be an oxygenated hydrocarbon lipid molecule. 2-Oxohexane is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Oxohexane is an ethereal tasting compound. Outside of the human body, 2-Oxohexane is found, on average, in the highest concentration within hyssops and milk (cow). 2-Oxohexane has also been detected, but not quantified in, several different foods, such as red bell peppers, nuts, corns, yellow bell peppers, and pepper (c. annuum). This could make 2-oxohexane a potential biomarker for the consumption of these foods. 2-Oxohexane is absorbed via ingestion, inhalation, and dermal routes, then distributed widely throughout the body, with the highest levels in the liver and blood. 2-Oxohexane is a potentially toxic compound. 2-Oxohexane, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, crohn's disease, and nonalcoholic fatty liver disease; 2-oxohexane has also been linked to the inborn metabolic disorder celiac disease. 2-Oxohexane is occasionally found as a volatile component of normal human biofluids. 2-Oxohexane is a volatile organic compound. 2-Oxohexane and 2,5-hexanedione may also inhibit sulfhydryl-dependent enzymes such as fructose-6-phosphate kinase and glyceraldehyde-3-phosphate dehydrogenase, as well as certain creatine kinases and adenylate kinases, impairing energy metabolism and subsequently resulting in axon deterioration. Breathing 2-Oxohexane affects the nervous and reproductive systems. The main neurological disorders associated with chronic volatile substance are peripheral neuropathy, cerebellar disease, chronic encephalopathy and dementia. Apart from peripheral neuropathy, the clinical features are non-specific, evidence for solvent-related toxicity is in most cases circumstantial and there is no clear dose/response relationship.
Structure
Data?1582752367
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Hexan-2-oneHMDB
2-HexanoneHMDB
2-Hexanone methyl N-butyl ketoneHMDB
Butyl methyl ketoneHMDB
Methyl butyl ketoneHMDB
Methyl N-butyl ketoneHMDB
MNBKHMDB
N-Butyl methyl ketoneHMDB
N-C4H9COCH3HMDB
PropylacetoneHMDB
Butylmethyl ketoneHMDB
Ketone, butylmethylHMDB
2 HexanoneHMDB
Hexan 2 oneHMDB
Ketone, methyl N-butylHMDB
Methyl N butyl ketoneHMDB
N-Butyl ketone, methylHMDB
Chemical FormulaC6H12O
Average Molecular Weight100.1589
Monoisotopic Molecular Weight100.088815006
IUPAC Namehexan-2-one
Traditional Namehexanone
CAS Registry Number591-78-6
SMILES
CCCCC(C)=O
InChI Identifier
InChI=1S/C6H12O/c1-3-4-5-6(2)7/h3-5H2,1-2H3
InChI KeyQQZOPKMRPOGIEB-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

Route of exposure:

Biological location:

Source:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-55.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility17.5 mg/mL at 20 °CNot Available
LogP1.38HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility8.14 g/LALOGPS
logP1.45ALOGPS
logP1.7ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)19.64ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity30.02 m³·mol⁻¹ChemAxon
Polarizability12.26 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)splash10-052f-9000000000-b9a2ab16adfdd94ece2aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-c9c9e98957d1fde0dce7Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-a8db7120c386c93d25ffSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-858b1e62ef5dfd041bafSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-e2acd59c62ae4caefc56Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-b9a2ab16adfdd94ece2aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-c9c9e98957d1fde0dce7Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-a8db7120c386c93d25ffSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-858b1e62ef5dfd041bafSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-e2acd59c62ae4caefc56Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-0884cf76c54fac458024Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-052f-9000000000-b9a2ab16adfdd94ece2aSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-052f-9000000000-c9c9e98957d1fde0dce7Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-052f-9000000000-214c4efe96ae363515d5Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HP 5970) , Positivesplash10-0006-9000000000-858b1e62ef5dfd041bafSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-052f-9000000000-e2acd59c62ae4caefc56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-8900000000-7f95c62c199ac18bb617Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f8c-9300000000-86d93f8a23031d700516Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-52c2a4eb34b81253f5b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-e69f92c1ea30b1c8b758Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-b2aac1a98aa5c3d5501eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5c-9000000000-a65bc7e7cdfb70bec9dbSpectrum
MSMass Spectrum (Electron Ionization)splash10-052f-9000000000-f15df0bf9af914ce3f16Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Urine
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
FecesDetected but not Quantified Adult (>18 years old)Both
Normal		 details
FecesDetected but not Quantified Adult (>18 years old)Not Specified
Normal		 details
FecesDetected and Quantified0-70720.958 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal		 details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal		 details
UrineDetected but not Quantified Adult (>18 years old)BothNormal 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)BothCrohns disease details
FecesDetected but not Quantified Adult (>18 years old)BothUlcerative colitis details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative colitis		 details
FecesDetected but not Quantified Adult (>18 years old)Both
Crohn's disease 		details
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)		 details
FecesDetected and Quantified0-1158026.562 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease		 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. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
  3. 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 ]
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 ]
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 ]
Crohn's disease
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
  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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008079
KNApSAcK IDNot Available
Chemspider ID11095
KEGG Compound IDNot Available
BioCyc ID2K-ADIPATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11583
PDB IDNot Available
ChEBI ID421633
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [PubMed:5556886 ]
  2. Griffin JW: Hexacarbon neurotoxicity. Neurobehav Toxicol Teratol. 1981 Winter;3(4):437-44. [PubMed:6278344 ]
  3. Lolin Y: Chronic neurological toxicity associated with exposure to volatile substances. Hum Toxicol. 1989 Jul;8(4):293-300. [PubMed:2550357 ]