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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:43:48 UTC
Update Date2019-07-23 06:08:56 UTC
HMDB IDHMDB0031519
Secondary Accession Numbers
  • HMDB31519
Metabolite Identification
Common Name4-Mercapto-4-methyl-2-pentanone
Description4-Mercapto-4-methyl-2-pentanone, also known as 4-sulfanyl-4-methylpentan-2-one or 4-methyl-4-sulfanyl-2-pentanone, 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, 4-mercapto-4-methyl-2-pentanone is considered to be an oxygenated hydrocarbon lipid molecule. An alkylthiol that is 4-methylpentan-2-one substituted at position 4 by a mercapto group. 4-Mercapto-4-methyl-2-pentanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Mercapto-4-methyl-2-pentanone is a blackcurrant, box tree, and cat-urine tasting compound. Outside of the human body, 4-Mercapto-4-methyl-2-pentanone has been detected, but not quantified in, alcoholic beverages. This could make 4-mercapto-4-methyl-2-pentanone a potential biomarker for the consumption of these foods.
Structure
Data?1563862136
Synonyms
ValueSource
4-Methyl-4-mercapto-2-pentanoneChEBI
4-Methyl-4-mercaptopentan-2-oneChEBI
4-Methyl-4-sulfanyl-2-pentanoneChEBI
4-Methyl-4-thiolpentan-2-oneChEBI
4-Sulfanyl-4-methylpentan-2-oneChEBI
4-Sulphanyl-4-methylpentan-2-oneChEBI
4-Methyl-4-sulphanyl-2-pentanoneGenerator
4-Mercapto-4-methyl-pentan-2-oneHMDB
4-Mercapto-4-methylpentan-2-oneHMDB
4-Methyl-4-mercapto-pentan-2-oneHMDB
4-Mercapto-4-methyl-2-pentanoneChEBI
Chemical FormulaC6H12OS
Average Molecular Weight132.224
Monoisotopic Molecular Weight132.060885696
IUPAC Name4-methyl-4-sulfanylpentan-2-one
Traditional Name4-methyl-4-sulfanylpentan-2-one
CAS Registry Number19872-52-7
SMILES
CC(=O)CC(C)(C)S
InChI Identifier
InChI=1S/C6H12OS/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H3
InChI KeyQRNZMFDCKKEPSX-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
  • Alkylthiol
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.22 g/LALOGPS
logP2.01ALOGPS
logP1.27ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)9.92ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.78 m³·mol⁻¹ChemAxon
Polarizability14.61 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9100000000-8e9ff8d3dd57a941e176Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-3900000000-f7c166c594ab2f5bd9e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-7900000000-415b660e2464f89dc70eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9100000000-cf87bb56a906d8284051Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001j-7900000000-67facb7cefc788001bd4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-9600000000-5a2f4ae474d4a47b0bebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9100000000-7653612fbae5886b1570Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008119
KNApSAcK IDNot Available
Chemspider ID79650
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Mercapto-4-methyl-2-pentanone
METLIN IDNot Available
PubChem Compound88290
PDB IDNot Available
ChEBI ID77856
Food Biomarker OntologyNot Available
VMH IDNot Available
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.. .