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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:37:40 UTC
Update Date2019-07-23 06:23:41 UTC
HMDB IDHMDB0037383
Secondary Accession Numbers
  • HMDB37383
Metabolite Identification
Common NameWithangulatin A
Description(S)-Menthone 8-thioacetate, also known as 8-acetylthio-p-menthanone-3 or fema 3809, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes (S)-Menthone 8-thioacetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563863021
Synonyms
ValueSource
(S)-Menthone 8-thioacetic acidGenerator
8-Acetylthio-p-menthanone-3HMDB
FEMA 3809HMDB
Menthone 8-thioacetateHMDB
15-[1-(4,5-Dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetic acidGenerator
Chemical FormulaC30H38O8
Average Molecular Weight526.6179
Monoisotopic Molecular Weight526.256668192
IUPAC Name15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate
Traditional Name15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate
CAS Registry Number120824-03-5
SMILES
CC(C1CC(C)=C(C)C(=O)O1)C1=CC(OC(C)=O)C2(O)C3CC4OC44C(O)C=CC(=O)C4(C)C3CCC12C
InChI Identifier
InChI=1S/C30H38O8/c1-14-11-21(37-26(34)15(14)2)16(3)19-12-24(36-17(4)31)29(35)20-13-25-30(38-25)23(33)8-7-22(32)28(30,6)18(20)9-10-27(19,29)5/h7-8,12,16,18,20-21,23-25,33,35H,9-11,13H2,1-6H3
InChI KeyPLPXOWZTDPJPHC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • Monocyclic monoterpenoid
  • P-menthane monoterpenoid
  • Ketone
  • Thiocarboxylic acid ester
  • Cyclic ketone
  • Carbothioic s-ester
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carbonyl group
  • Organosulfur compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Route of exposure:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point152 - 153 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.032 g/LALOGPS
logP2.33ALOGPS
logP2.9ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)12.96ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area122.66 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity138.08 m³·mol⁻¹ChemAxon
Polarizability56.63 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-4242910000-9595aac528eefe6fdc68Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a4l-5030179000-2883be337aa9cd352eb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0000960000-fc7e633a9800625e15ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0rk9-3101920000-303249a9c7ffd40fcbf6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0i00-8205920000-712e6bcf5183fb5365fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-2000960000-a6049f959c19cb2507d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0560-3100930000-d9b5414512e0ea3577e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200200000-acd18709e7aeca24d16dSpectrum
Biological Properties
Cellular Locations
  • 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 IDFDB016428
KNApSAcK IDNot Available
Chemspider ID83635
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92649
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.