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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:42:58 UTC
Update Date2021-10-13 06:15:36 UTC
HMDB IDHMDB0031409
Secondary Accession Numbers
  • HMDB31409
Metabolite Identification
Common Name2-Decanone
Description2-Decanone, also known as N-C8H17COCH3 or decan-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-decanone is considered to be an oxygenated hydrocarbon lipid molecule. A methyl ketone that is decane in which the methylene hydrogens at position 2 are replaced by an oxo group. 2-Decanone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2-Decanone is found, on average, in the highest concentration within kohlrabis. This could make 2-decanone a potential biomarker for the consumption of these foods. 2-Decanone, with regard to humans, has been found to be associated with several diseases such as nonalcoholic fatty liver disease, ulcerative colitis, and crohn's disease; 2-decanone has also been linked to the inborn metabolic disorder celiac disease.
Structure
Data?1563862122
Synonyms
ValueSource
Methyl N-octyl ketoneChEBI
Methyl octyl ketoneChEBI
N-C8H17COCH3ChEBI
Octyl methyl ketoneChEBI
Decan-2-oneHMDB
Decanedioic acid, monoethyl esterHMDB
2-DecanoneChEBI
Chemical FormulaC10H20O
Average Molecular Weight156.2652
Monoisotopic Molecular Weight156.151415262
IUPAC Namedecan-2-one
Traditional Name2-decanone
CAS Registry Number693-54-9
SMILES
CCCCCCCCC(C)=O
InChI Identifier
InChI=1S/C10H20O/c1-3-4-5-6-7-8-9-10(2)11/h3-9H2,1-2H3
InChI KeyZAJNGDIORYACQU-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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point14 °CNot Available
Boiling Point210.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.077 mg/mL at 25 °CNot Available
LogP3.73Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.038 g/LALOGPS
logP10(3.63) g/LALOGPS
logP10(3.47) g/LChemAxon
logS10(-3.6) g/LALOGPS
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 Count7ChemAxon
Refractivity48.43 m³·mol⁻¹ChemAxon
Polarizability20.55 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+139.21231661259
DarkChem[M-H]-136.65331661259
DeepCCS[M+H]+146.12230932474
DeepCCS[M-H]-143.22230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-DecanoneCCCCCCCCC(C)=O1488.4Standard polar33892256
2-DecanoneCCCCCCCCC(C)=O1169.0Standard non polar33892256
2-DecanoneCCCCCCCCC(C)=O1191.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Decanone,1TMS,isomer #1CCCCCCCC=C(C)O[Si](C)(C)C1377.4Semi standard non polar33892256
2-Decanone,1TMS,isomer #1CCCCCCCC=C(C)O[Si](C)(C)C1343.2Standard non polar33892256
2-Decanone,1TMS,isomer #2C=C(CCCCCCCC)O[Si](C)(C)C1343.9Semi standard non polar33892256
2-Decanone,1TMS,isomer #2C=C(CCCCCCCC)O[Si](C)(C)C1348.2Standard non polar33892256
2-Decanone,1TBDMS,isomer #1CCCCCCCC=C(C)O[Si](C)(C)C(C)(C)C1597.3Semi standard non polar33892256
2-Decanone,1TBDMS,isomer #1CCCCCCCC=C(C)O[Si](C)(C)C(C)(C)C1529.2Standard non polar33892256
2-Decanone,1TBDMS,isomer #2C=C(CCCCCCCC)O[Si](C)(C)C(C)(C)C1553.8Semi standard non polar33892256
2-Decanone,1TBDMS,isomer #2C=C(CCCCCCCC)O[Si](C)(C)C(C)(C)C1533.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Decanone EI-B (Non-derivatized)splash10-0a4l-9000000000-19def653e5bb9fe848062017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Decanone EI-B (Non-derivatized)splash10-0a4l-9000000000-19def653e5bb9fe848062018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Decanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-23bdc1d44eec062c68fb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Decanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4l-9000000000-3cfb3d0c237791cbce2a2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decanone 10V, Positive-QTOFsplash10-0a4r-0900000000-721680b316eacc1ff3fd2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decanone 20V, Positive-QTOFsplash10-052r-8900000000-6ae362282a577df917d32016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decanone 40V, Positive-QTOFsplash10-052f-9000000000-a4c76405ce0c4f60b4c82016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decanone 10V, Negative-QTOFsplash10-0a4i-0900000000-1f9fc80a0eebe31f13f52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decanone 20V, Negative-QTOFsplash10-0a4i-2900000000-7d96fd749bce166faa552016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decanone 40V, Negative-QTOFsplash10-0a4r-9200000000-8418a99e41666c4ac8ef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decanone 10V, Negative-QTOFsplash10-0a4i-0900000000-f6034c6a8245c68a37ac2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decanone 20V, Negative-QTOFsplash10-0a4i-0900000000-c0f21b08bc5ce30b8ec12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decanone 40V, Negative-QTOFsplash10-052f-9000000000-6dd39f7eb4d1468d62d72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decanone 10V, Positive-QTOFsplash10-0aor-9100000000-944f8ef456819ebc5d212021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decanone 20V, Positive-QTOFsplash10-0aou-9000000000-73704d49f59f25e7e1902021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Decanone 40V, Positive-QTOFsplash10-0006-9000000000-3863abf647177cdc1deb2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0-31186.300 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected and Quantified0-49211.213 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
Associated Disorders and Diseases
Disease References
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. 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 ]
Ulcerative colitis
  1. 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
FooDB IDFDB003484
KNApSAcK IDC00034760
Chemspider ID12218
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12741
PDB IDNot Available
ChEBI ID77929
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1047071
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .