Human Metabolome Database: Showing metabocard for 2-Heptanone (HMDB0003671)

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Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2006-08-13 02:57:08 UTC

Update Date

2020-02-26 21:24:45 UTC

HMDB ID

HMDB0003671

Secondary Accession Numbers

HMDB03671

Metabolite Identification

Common Name

2-Heptanone

Description

2-Heptanone, also known as butylacetone or heptan-2-one, 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-heptanone is considered to be an oxygenated hydrocarbon lipid molecule. 2-Heptanone is a ketone with the molecular formula C7H14O. 2-Heptanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Heptanone exists in all living species, ranging from bacteria to humans. 2-Heptanone is a sweet, cinnamon, and coconut tasting compound. Outside of the human body, 2-Heptanone is found, on average, in the highest concentration within a few different foods, such as corns, milk (cow), and peppermints. 2-Heptanone has also been detected, but not quantified in, several different foods, such as tarragons, blackberries, tortilla chips, ceylon cinnamons, and evergreen blackberries. This could make 2-heptanone a potential biomarker for the consumption of these foods. 2-Heptanone is one of the metabolites of n-heptane found in the urine of employees exposed to heptane in shoe and tire factories. 2-Heptanone, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, nonalcoholic fatty liver disease, crohn's disease, and hepatic encephalopathy; 2-heptanone has also been linked to the inborn metabolic disorder celiac disease. It is a colorless to white liquid with a banana-like, fruity odor.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Butylacetone	ChEBI
Methyl N-amyl ketone	ChEBI
Methyl pentyl ketone	ChEBI
N-Amyl methyl ketone	ChEBI
N-Pentyl methyl ketone	ChEBI
Heptan-2-one	Kegg
1-Methylhexanal	HMDB
2-Oxoheptane	HMDB
Amyl methyl ketone	HMDB
Methyl amyl ketone	HMDB
Methyl N-pentyl ketone	HMDB
Pentyl methyl ketone	HMDB
Methyl-N-amyl ketone	HMDB
2-Heptanone	ChEBI

Chemical Formula

C₇H₁₄O

Average Molecular Weight

114.1855

Monoisotopic Molecular Weight

114.10446507

IUPAC Name

heptan-2-one

Traditional Name

2-heptanone

CAS Registry Number

110-43-0

SMILES

CCCCCC(C)=O

InChI Identifier

InChI=1S/C7H14O/c1-3-4-5-6-7(2)8/h3-6H2,1-2H3

InChI Key

CATSNJVOTSVZJV-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

methyl ketone (CHEBI:5672 )
dialkyl ketone (CHEBI:5672 )
Oxygenated hydrocarbons (C08380 )
Oxygenated hydrocarbons (LMFA12000004 )

Ontology

Physiological effect

Health effect:

Health condition:

Hepatobiliary disorders:

Hepatic encephalopathy

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Subcellular:

Biofluid and excreta:

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-35 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4.3 mg/mL at 25 °C	Not Available
LogP	1.98	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
Water Solubility	2.26 g/L	ALOGPS
logP	1.92	ALOGPS
logP	2.14	ChemAxon
logS	-1.7	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	4	ChemAxon
Refractivity	34.62 m³·mol⁻¹	ChemAxon
Polarizability	14.31 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-9000000000-91b562632b96c4162a98	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-67e38b971af9b3c9eab2	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9000000000-91a94dcd78168a9329dd	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-91b562632b96c4162a98	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-052f-9000000000-67e38b971af9b3c9eab2	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-9000000000-91a94dcd78168a9329dd	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-bce74b4c35b3b9e36244	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-9000000000-340ccee799fd50ab5a33	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-0fd345f1dea8cedcab42	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-f99f3bb1427948d03185	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-052f-9000000000-97b7fddf959ef5d3b440	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-052f-9000000000-67e38b971af9b3c9eab2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-0a4i-9000000000-91a94dcd78168a9329dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-9800000000-6a3dc0c3384cd6612eff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-9200000000-5a05142154c02577b232	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-2d6778d58ba8e8ea00a8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1900000000-ed3177cddff3fa618b12	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-6900000000-25ce7fee81ab8707f58b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4m-9000000000-5ada47c45a2fe1735d19	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-e42425c6c304ff44687b	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

Membrane (predicted from logP)

Biospecimen Locations

Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0 - 0.18 uM	Adult (>18 years old)	Both	Normal	7320160	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	14684577	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	17314143	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	26806034	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	20055983	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	23454028	details
Feces	Detected but not Quantified		Adult (>18 years old)	Not Specified	Normal	21494609	details
Feces	Detected but not Quantified		Newborn (0-30 days old)	Both	Normal	21386183	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	21386183	details
Feces	Detected and Quantified	2072.651-22215.313 nmol/g wet feces	Children (1-13 years old)	Not Specified	Normal	21970810	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Not Specified	Normal	24421258	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Normal	22284503	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.7 uM	Adult (>18 years old)	Both	Hepatic encephalopathy	7320160	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Campylobacter jejuni infection	17314143	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Clostridium difficile infection	17314143	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Ulcerative Colitis	17314143	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Crohns disease	26806034	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Ulcerative colitis	26806034	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	23454028	details
Feces	Detected and Quantified	0-479132.639 nmol/g wet feces	Children (1-13 years old)	Not Specified	Treated celiac disease	21970810	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Breast cancer	22284503	details

Associated Disorders and Diseases

Disease References

Hepatic encephalopathy
Goldberg EM, Blendis LM, Sandler S: A gas chromatographic--mass spectrometric study of profiles of volatile metabolites in hepatic encephalopathy. J Chromatogr. 1981 Dec 11;226(2):291-9. [PubMed:7320160 ]
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 ] 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
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 ]
Perillyl alcohol administration for cancer treatment
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 ]