Human Metabolome Database: Showing metabocard for 2-Oxohexane (HMDB0005842)

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Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2007-04-12 15:37:12 UTC

Update Date

2020-04-08 20:50:00 UTC

HMDB ID

HMDB0005842

Secondary Accession Numbers

HMDB05842

Metabolite Identification

Common Name

2-Oxohexane

Description

2-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 a few different foods, such as hyssops, milk (cow), and corns. 2-Oxohexane has also been detected, but not quantified in, several different foods, such as green bell peppers, orange bell peppers, red bell peppers, nuts, and peppers. This could make 2-oxohexane a potential biomarker for the consumption of these foods. 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 absorbed via ingestion, inhalation, and dermal routes, then distributed widely throughout the body, with the highest levels in the liver and blood. The main neurological disorders associated with chronic volatile substance are peripheral neuropathy, cerebellar disease, chronic encephalopathy and dementia. This may include pathologies such as peripheral neuropathy and developmental defects. 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. 2-Oxohexane is occasionally found as a volatile component of normal human biofluids. In addition, 2,5-hexanedione can covalently cross-links neurofilaments, causing large axonal swellings. 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.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Hexan-2-one	HMDB
2-Hexanone	HMDB
2-Hexanone methyl N-butyl ketone	HMDB
Butyl methyl ketone	HMDB
Methyl butyl ketone	HMDB
Methyl N-butyl ketone	HMDB
MNBK	HMDB
N-Butyl methyl ketone	HMDB
N-C4H9COCH3	HMDB
Propylacetone	HMDB
Butylmethyl ketone	HMDB
Ketone, butylmethyl	HMDB
2 Hexanone	HMDB
Hexan 2 one	HMDB
Ketone, methyl N-butyl	HMDB
Methyl N butyl ketone	HMDB
N-Butyl ketone, methyl	HMDB
2-Oxohexane	HMDB
MBK	HMDB

Chemical Formula

C₆H₁₂O

Average Molecular Weight

100.1589

Monoisotopic Molecular Weight

100.088815006

IUPAC Name

hexan-2-one

Traditional Name

hexanone

CAS Registry Number

591-78-6

SMILES

CCCCC(C)=O

InChI Identifier

InChI=1S/C6H12O/c1-3-4-5-6(2)7/h3-5H2,1-2H3

InChI Key

QQZOPKMRPOGIEB-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Ketones

Alternative Parents

Substituents

Ketone
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Oxygenated hydrocarbons (LMFA12000048 )

Ontology

Physiological effect

Health effect:

Health condition:

Peripheral neuropathy

Observation:

Neuropathy

Ingestion

Biological location:

Biofluid and excreta:

Source:

Biological:

Plant:

Poaceae

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-55.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	17.5 mg/mL at 20 °C	Not Available
LogP	1.38	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
Water Solubility	8.14 g/L	ALOGPS
logP	1.45	ALOGPS
logP	1.7	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	19.64	ChemAxon
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	30.02 m³·mol⁻¹	ChemAxon
Polarizability	12.26 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-b9a2ab16adfdd94ece2a	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-c9c9e98957d1fde0dce7	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-a8db7120c386c93d25ff	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-858b1e62ef5dfd041baf	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-e2acd59c62ae4caefc56	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-b9a2ab16adfdd94ece2a	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-c9c9e98957d1fde0dce7	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-a8db7120c386c93d25ff	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-858b1e62ef5dfd041baf	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-e2acd59c62ae4caefc56	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-0884cf76c54fac458024	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-052f-9000000000-b9a2ab16adfdd94ece2a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-052f-9000000000-c9c9e98957d1fde0dce7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-052f-9000000000-214c4efe96ae363515d5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HP 5970) , Positive	splash10-0006-9000000000-858b1e62ef5dfd041baf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-052f-9000000000-e2acd59c62ae4caefc56	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ue9-8900000000-7f95c62c199ac18bb617	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f8c-9300000000-86d93f8a23031d700516	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-52c2a4eb34b81253f5b0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-e69f92c1ea30b1c8b758	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9000000000-b2aac1a98aa5c3d5501e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a5c-9000000000-a65bc7e7cdfb70bec9db	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-052f-9000000000-f15df0bf9af914ce3f16	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	26806034	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24811995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23454028	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	21494609	details
Feces	Detected and Quantified	0-70720.958 nmol/g wet feces	Children (1-13 years old)	Not Specified	Normal	21970810	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19167006	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Campylobacter jejuni infection	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Clostridium difficile infection	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative Colitis	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohns disease	26806034	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	26806034	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	24811995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohn's disease	24811995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	23454028	details
Feces	Detected and Quantified	0-1158026.562 nmol/g wet feces	Children (1-13 years old)	Not Specified	Treated celiac disease	21970810	details

Associated Disorders and Diseases

Disease References

Ulcerative colitis
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 ] 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 ] 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
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
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
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 ] 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

212750 (Celiac disease)
266600 (Crohn's disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008079

KNApSAcK ID

Not Available

Chemspider ID

11095

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11583

PDB ID

Not Available

ChEBI ID

89206

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [PubMed:5556886 ]
Griffin JW: Hexacarbon neurotoxicity. Neurobehav Toxicol Teratol. 1981 Winter;3(4):437-44. [PubMed:6278344 ]
Lolin Y: Chronic neurological toxicity associated with exposure to volatile substances. Hum Toxicol. 1989 Jul;8(4):293-300. [PubMed:2550357 ]

Showing metabocard for 2-Oxohexane (HMDB0005842)

Structure for HMDB0005842 (2-Oxohexane)