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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:44:00 UTC
Update Date2022-03-07 02:53:01 UTC
HMDB IDHMDB0031549
Secondary Accession Numbers
  • HMDB31549
Metabolite Identification
Common Name5-Methyl-2-hexanone
Description5-Methyl-2-hexanone, also known as methyl isoamyl ketone or MIAK, 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. 5-Methyl-2-hexanone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, 5-methyl-2-hexanone is considered to be an oxygenated hydrocarbon lipid molecule. 5-Methyl-2-hexanone has been detected, but not quantified, in a few different foods, such as eggs, fruits, and tea. This could make 5-methyl-2-hexanone a potential biomarker for the consumption of these foods.
Structure
Data?1563862139
Synonyms
ValueSource
(CH3)2chch2ch2coch3HMDB
2-Hexanone-5-methylHMDB
2-Methyl-5-hexanoneHMDB
5-Methylhexan-2-oneHMDB
Isoamyl methyl ketoneHMDB
IsobutylacetoneHMDB
Isopentyl methyl ketoneHMDB
Ketone, methyl isoamylHMDB
Methyl isoamyl ketoneHMDB
Methyl isopentyl ketoneHMDB
MIAKHMDB
Chemical FormulaC7H14O
Average Molecular Weight114.1855
Monoisotopic Molecular Weight114.10446507
IUPAC Name5-methylhexan-2-one
Traditional Name5-methyl-2-hexanone
CAS Registry Number110-12-3
SMILES
CC(C)CCC(C)=O
InChI Identifier
InChI=1S/C7H14O/c1-6(2)4-5-7(3)8/h6H,4-5H2,1-3H3
InChI KeyFFWSICBKRCICMR-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
Disposition
Process
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-74 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.4 mg/mL at 25 °CNot Available
LogP1.88Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.1 g/LALOGPS
logP1.88ALOGPS
logP1.98ChemAxon
logS-1.6ALOGPS
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
Refractivity34.57 m³·mol⁻¹ChemAxon
Polarizability14.12 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]+126.64131661259
DarkChem[M-H]-120.85631661259
DeepCCS[M+H]+132.2530932474
DeepCCS[M-H]-130.29430932474
DeepCCS[M-2H]-166.20430932474
DeepCCS[M+Na]+140.82430932474
AllCCS[M+H]+126.932859911
AllCCS[M+H-H2O]+122.632859911
AllCCS[M+NH4]+130.932859911
AllCCS[M+Na]+132.032859911
AllCCS[M-H]-131.232859911
AllCCS[M+Na-2H]-134.532859911
AllCCS[M+HCOO]-138.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Methyl-2-hexanoneCC(C)CCC(C)=O1142.3Standard polar33892256
5-Methyl-2-hexanoneCC(C)CCC(C)=O825.8Standard non polar33892256
5-Methyl-2-hexanoneCC(C)CCC(C)=O847.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Methyl-2-hexanone,1TMS,isomer #1CC(=CCC(C)C)O[Si](C)(C)C1056.5Semi standard non polar33892256
5-Methyl-2-hexanone,1TMS,isomer #1CC(=CCC(C)C)O[Si](C)(C)C1011.2Standard non polar33892256
5-Methyl-2-hexanone,1TMS,isomer #2C=C(CCC(C)C)O[Si](C)(C)C1027.9Semi standard non polar33892256
5-Methyl-2-hexanone,1TMS,isomer #2C=C(CCC(C)C)O[Si](C)(C)C1029.8Standard non polar33892256
5-Methyl-2-hexanone,1TBDMS,isomer #1CC(=CCC(C)C)O[Si](C)(C)C(C)(C)C1272.1Semi standard non polar33892256
5-Methyl-2-hexanone,1TBDMS,isomer #1CC(=CCC(C)C)O[Si](C)(C)C(C)(C)C1231.8Standard non polar33892256
5-Methyl-2-hexanone,1TBDMS,isomer #2C=C(CCC(C)C)O[Si](C)(C)C(C)(C)C1233.2Semi standard non polar33892256
5-Methyl-2-hexanone,1TBDMS,isomer #2C=C(CCC(C)C)O[Si](C)(C)C(C)(C)C1232.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 5-Methyl-2-hexanone EI-B (Non-derivatized)splash10-0006-9000000000-154c06a6e349e40781722017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Methyl-2-hexanone EI-B (Non-derivatized)splash10-052f-9000000000-dbf6e4e2149ba1271e572017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Methyl-2-hexanone EI-B (Non-derivatized)splash10-0006-9000000000-40a76a6003700e8075472017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Methyl-2-hexanone EI-B (Non-derivatized)splash10-0a4l-9000000000-b38c5127376d7279ee3b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Methyl-2-hexanone EI-B (Non-derivatized)splash10-0006-9000000000-154c06a6e349e40781722018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Methyl-2-hexanone EI-B (Non-derivatized)splash10-052f-9000000000-dbf6e4e2149ba1271e572018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Methyl-2-hexanone EI-B (Non-derivatized)splash10-0006-9000000000-40a76a6003700e8075472018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Methyl-2-hexanone EI-B (Non-derivatized)splash10-0a4l-9000000000-b38c5127376d7279ee3b2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyl-2-hexanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-e94e92815bffdc7c187c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyl-2-hexanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methyl-2-hexanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-fee4d6523daaedc7f2a22014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2-hexanone 10V, Positive-QTOFsplash10-014j-9700000000-ae3a9550acdb4943f0ab2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2-hexanone 20V, Positive-QTOFsplash10-05mk-9300000000-f712ed1d2d0c0cf3ffd02016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2-hexanone 40V, Positive-QTOFsplash10-0a4l-9000000000-8da071fb3a30f6d522142016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2-hexanone 10V, Negative-QTOFsplash10-03di-2900000000-d2779a9178572f90a7582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2-hexanone 20V, Negative-QTOFsplash10-03di-7900000000-e4b6b80c9d0671fa1ac92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2-hexanone 40V, Negative-QTOFsplash10-0a4i-9000000000-64282375abfc9fcea8d12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2-hexanone 10V, Negative-QTOFsplash10-03di-0900000000-87ba7764343ecec4c93f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2-hexanone 20V, Negative-QTOFsplash10-03dm-9600000000-d759f296eef93bd32b962021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2-hexanone 40V, Negative-QTOFsplash10-0a4i-9000000000-f3e8f5b90952021f423e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2-hexanone 10V, Positive-QTOFsplash10-0ac1-9000000000-4cce207a5ae79e383a1c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2-hexanone 20V, Positive-QTOFsplash10-0a4i-9000000000-84ea496df8600240ed482021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methyl-2-hexanone 40V, Positive-QTOFsplash10-0536-9000000000-925f87503ced06036d962021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
  • Saliva
  • Urine
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 but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
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 ]
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 IDFDB008160
KNApSAcK IDC00052167
Chemspider ID7743
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8034
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .