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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:41:48 UTC
Update Date2022-03-07 02:52:53 UTC
HMDB IDHMDB0031242
Secondary Accession Numbers
  • HMDB31242
Metabolite Identification
Common NameDihydro-3(2H)-thiophenone
DescriptionDihydro-3(2H)-thiophenone belongs to the class of organic compounds known as thiolanes. These are organic compounds containing thiolane, a five-member saturated ring containing four carbon atoms and a sulfur atom. Dihydro-3(2H)-thiophenone is a buttery, clam, and garlic tasting compound. Dihydro-3(2H)-thiophenone has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, nuts, and robusta coffees (Coffea canephora). This could make dihydro-3(2H)-thiophenone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dihydro-3(2H)-thiophenone.
Structure
Data?1563862099
Synonyms
ValueSource
3-oxo-2,3,4, 5-TetrahydrothiopheneHMDB
3-oxo-2,3,4,5-TetrahydrothiopheneHMDB
3-OxotetrahydrothiopheneHMDB
3-TetrahydrothiophenoneHMDB
3-ThiacyclopentanoneHMDB
3-ThiolanoneHMDB
3-ThiophanoneHMDB
4,5-dihydro-3(2H)ThiophenoneHMDB
dihydro-3-(2H)-ThiophenoneHMDB
dihydro-3-(2H)-Thiophenone (tetrahydrothiophen-3-one)HMDB
Dihydrothiophen-3(2H)-oneHMDB
FEMA 3266HMDB
tetrahydro-Thiophen-3-oneHMDB
Tetrahydrothiophen-3-oneHMDB
Tetrahydrothiophene-3-oneHMDB
Thiolan-3-oneHMDB
Chemical FormulaC4H6OS
Average Molecular Weight102.155
Monoisotopic Molecular Weight102.013935504
IUPAC Namethiolan-3-one
Traditional Namethiolan-3-one
CAS Registry Number1003-04-9
SMILES
O=C1CCSC1
InChI Identifier
InChI=1S/C4H6OS/c5-4-1-2-6-3-4/h1-3H2
InChI KeyDSXFPRKPFJRPIB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thiolanes. These are organic compounds containing thiolane, a five-member saturated ring containing four carbon atoms and a sulfur atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassThiolanes
Sub ClassNot Available
Direct ParentThiolanes
Alternative Parents
Substituents
  • Thiolane
  • Cyclic ketone
  • Ketone
  • Dialkylthioether
  • Thioether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point175.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility192400 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.222 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility38.4 g/LALOGPS
logP-0.1ALOGPS
logP0.55ChemAxon
logS-0.43ALOGPS
pKa (Strongest Acidic)18.41ChemAxon
pKa (Strongest Basic)-7.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.86 m³·mol⁻¹ChemAxon
Polarizability10.17 ųChemAxon
Number of Rings1ChemAxon
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]+118.25531661259
DarkChem[M-H]-112.16431661259
DeepCCS[M+H]+126.7830932474
DeepCCS[M-H]-124.72230932474
DeepCCS[M-2H]-160.20430932474
DeepCCS[M+Na]+134.58730932474
AllCCS[M+H]+118.532859911
AllCCS[M+H-H2O]+113.532859911
AllCCS[M+NH4]+123.232859911
AllCCS[M+Na]+124.532859911
AllCCS[M-H]-125.832859911
AllCCS[M+Na-2H]-129.532859911
AllCCS[M+HCOO]-133.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dihydro-3(2H)-thiophenoneO=C1CCSC11523.7Standard polar33892256
Dihydro-3(2H)-thiophenoneO=C1CCSC1931.1Standard non polar33892256
Dihydro-3(2H)-thiophenoneO=C1CCSC1956.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihydro-3(2H)-thiophenone,1TMS,isomer #1C[Si](C)(C)OC1=CSCC11222.1Semi standard non polar33892256
Dihydro-3(2H)-thiophenone,1TMS,isomer #1C[Si](C)(C)OC1=CSCC11209.3Standard non polar33892256
Dihydro-3(2H)-thiophenone,1TMS,isomer #2C[Si](C)(C)OC1=CCSC11216.7Semi standard non polar33892256
Dihydro-3(2H)-thiophenone,1TMS,isomer #2C[Si](C)(C)OC1=CCSC11211.6Standard non polar33892256
Dihydro-3(2H)-thiophenone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CSCC11434.8Semi standard non polar33892256
Dihydro-3(2H)-thiophenone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CSCC11432.5Standard non polar33892256
Dihydro-3(2H)-thiophenone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CCSC11436.0Semi standard non polar33892256
Dihydro-3(2H)-thiophenone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CCSC11417.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dihydro-3(2H)-thiophenone GC-MS (Non-derivatized) - 70eV, Positivesplash10-06vl-9000000000-8920a03b7f602925528c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydro-3(2H)-thiophenone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydro-3(2H)-thiophenone 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 - Dihydro-3(2H)-thiophenone 10V, Positive-QTOFsplash10-0udr-7900000000-d57d2cdd3d0696b386d42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-3(2H)-thiophenone 20V, Positive-QTOFsplash10-0udi-5900000000-a741a9b25e6b72552b402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-3(2H)-thiophenone 40V, Positive-QTOFsplash10-000i-9000000000-67d262f4d56bb8ebe8112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-3(2H)-thiophenone 10V, Negative-QTOFsplash10-0uk9-9700000000-a789186f119cc8dc97a52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-3(2H)-thiophenone 20V, Negative-QTOFsplash10-0zmi-9300000000-4852f51e992b471ea1d42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-3(2H)-thiophenone 40V, Negative-QTOFsplash10-0abc-9000000000-aa29fcae8cafcad89af62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-3(2H)-thiophenone 10V, Positive-QTOFsplash10-0udi-2900000000-de6a9b91fefe92c191862021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-3(2H)-thiophenone 20V, Positive-QTOFsplash10-0006-9100000000-e3567016322e7e5ca27d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-3(2H)-thiophenone 40V, Positive-QTOFsplash10-0006-9000000000-78ed59499ffbdf7655ba2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-3(2H)-thiophenone 10V, Negative-QTOFsplash10-0uyi-9400000000-ac091bff34a35585516b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-3(2H)-thiophenone 20V, Negative-QTOFsplash10-001i-9000000000-d508959c4a3b196a9a8e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydro-3(2H)-thiophenone 40V, Negative-QTOFsplash10-001i-9000000000-716139e2de81bc94af5f2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
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 IDFDB003269
KNApSAcK IDNot Available
Chemspider ID55193
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound61252
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1005811
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.. .