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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:49:18 UTC
Update Date2023-02-21 17:21:57 UTC
HMDB IDHMDB0032346
Secondary Accession Numbers
  • HMDB32346
Metabolite Identification
Common Name(+/-)-Isobutyl 3-methylthiobutyrate
Description(+/-)-Isobutyl 3-methylthiobutyrate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Based on a literature review a small amount of articles have been published on (+/-)-Isobutyl 3-methylthiobutyrate.
Structure
Data?1677000117
Synonyms
ValueSource
(+/-)-isobutyl 3-methylthiobutyric acidGenerator
Chemical FormulaC9H18O2S
Average Molecular Weight190.303
Monoisotopic Molecular Weight190.10275051
IUPAC Name2-methylpropyl 3-(methylsulfanyl)butanoate
Traditional Name2-methylpropyl 3-(methylsulfanyl)butanoate
CAS Registry Number127931-21-9
SMILES
CSC(C)CC(=O)OCC(C)C
InChI Identifier
InChI=1S/C9H18O2S/c1-7(2)6-11-9(10)5-8(3)12-4/h7-8H,5-6H2,1-4H3
InChI KeyRRGSLXQIRFOAEM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Carboxylic acid ester
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP2.9ALOGPS
logP2.54ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity52.71 m³·mol⁻¹ChemAxon
Polarizability21.54 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+146.51731661259
DarkChem[M-H]-142.31331661259
DeepCCS[M+H]+150.40330932474
DeepCCS[M-H]-146.68930932474
DeepCCS[M-2H]-184.05330932474
DeepCCS[M+Na]+159.71630932474
AllCCS[M+H]+143.432859911
AllCCS[M+H-H2O]+139.932859911
AllCCS[M+NH4]+146.632859911
AllCCS[M+Na]+147.632859911
AllCCS[M-H]-146.632859911
AllCCS[M+Na-2H]-148.532859911
AllCCS[M+HCOO]-150.732859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.6.34 minutes32390414
Predicted by Siyang on May 30, 202215.5549 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20220.87 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid26.5 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid2319.6 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid515.6 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid182.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid309.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid119.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid652.3 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid793.6 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)111.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1199.7 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid506.4 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1426.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid434.8 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid361.1 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate496.0 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA502.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water23.0 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(+/-)-Isobutyl 3-methylthiobutyrateCSC(C)CC(=O)OCC(C)C1714.9Standard polar33892256
(+/-)-Isobutyl 3-methylthiobutyrateCSC(C)CC(=O)OCC(C)C1309.8Standard non polar33892256
(+/-)-Isobutyl 3-methylthiobutyrateCSC(C)CC(=O)OCC(C)C1292.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (+/-)-Isobutyl 3-methylthiobutyrate GC-MS (Non-derivatized) - 70eV, Positivesplash10-05mo-9100000000-ced7a35496ae31632a092017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+/-)-Isobutyl 3-methylthiobutyrate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+/-)-Isobutyl 3-methylthiobutyrate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+/-)-Isobutyl 3-methylthiobutyrate 10V, Positive-QTOFsplash10-052f-7900000000-f30267590338bbcd52572016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+/-)-Isobutyl 3-methylthiobutyrate 20V, Positive-QTOFsplash10-0a4i-9200000000-05d3e0a7fdc8eb086d5c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+/-)-Isobutyl 3-methylthiobutyrate 40V, Positive-QTOFsplash10-0a4i-9000000000-24e1772cdc7f0681872f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+/-)-Isobutyl 3-methylthiobutyrate 10V, Negative-QTOFsplash10-00ks-6900000000-5b73c430c0015b7456c32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+/-)-Isobutyl 3-methylthiobutyrate 20V, Negative-QTOFsplash10-00kk-9400000000-d6e2194783f2261772892016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+/-)-Isobutyl 3-methylthiobutyrate 40V, Negative-QTOFsplash10-0002-9000000000-e0e4979704588fbffcb22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+/-)-Isobutyl 3-methylthiobutyrate 10V, Positive-QTOFsplash10-05p9-6900000000-41179848d2c3718c6e202021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+/-)-Isobutyl 3-methylthiobutyrate 20V, Positive-QTOFsplash10-0670-8900000000-54ebf1a8ff2c2a57d8112021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+/-)-Isobutyl 3-methylthiobutyrate 40V, Positive-QTOFsplash10-052e-9000000000-49c700413dfe9b4b8c492021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+/-)-Isobutyl 3-methylthiobutyrate 10V, Negative-QTOFsplash10-00di-9000000000-51362a6c9ddaac5c00e72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+/-)-Isobutyl 3-methylthiobutyrate 20V, Negative-QTOFsplash10-0002-9400000000-f26f4344c292271351352021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+/-)-Isobutyl 3-methylthiobutyrate 40V, Negative-QTOFsplash10-00di-9000000000-eedf58c025bfec0e2a102021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB009642
KNApSAcK IDNot Available
Chemspider ID21105925
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound54281757
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)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. (). EAFUS: Everything Added to Food in the United States.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.