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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:17:09 UTC

Update Date

2023-02-21 17:23:23 UTC

HMDB ID

HMDB0033548

Secondary Accession Numbers

HMDB33548

Metabolite Identification

Common Name

4-Hydroxy-5-methyl-3(2H)-thiophenone

Description

4-Hydroxy-5-methyl-3(2H)-thiophenone belongs to the class of organic compounds known as vinylogous thioesters. These are organic compounds containing a thioester group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety. Based on a literature review very few articles have been published on 4-Hydroxy-5-methyl-3(2H)-thiophenone.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₅H₆O₂S

Average Molecular Weight

130.165

Monoisotopic Molecular Weight

130.008850126

IUPAC Name

4-hydroxy-5-methyl-2,3-dihydrothiophen-3-one

Traditional Name

4-hydroxy-5-methyl-2H-thiophen-3-one

CAS Registry Number

26494-09-7

SMILES

CC1=C(O)C(=O)CS1

InChI Identifier

InChI=1S/C5H6O2S/c1-3-5(7)4(6)2-8-3/h7H,2H2,1H3

InChI Key

GIVVLEIYPVKDNV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vinylogous thioesters. These are organic compounds containing a thioester group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Vinylogous thioesters

Sub Class

Not Available

Direct Parent

Vinylogous thioesters

Alternative Parents

Substituents

Vinylogous thioester
2,3-dihydrothiophene
Cyclic ketone
Thioenolether
Ketone
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0033548)
Extracellular (HMDB: HMDB0033548)

Source

Exogenous

Exogenous (HMDB: HMDB0033548)

Food

Food (HMDB: HMDB0033548)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033548)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	23320 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	31.9 g/L	ALOGPS
logP	-0.02	ALOGPS
logP	0.12	ChemAxon
logS	-0.61	ALOGPS
pKa (Strongest Acidic)	4.97	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	34.97 m³·mol⁻¹	ChemAxon
Polarizability	12.36 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	128.705	30932474
DeepCCS	[M-H]-	126.614	30932474
DeepCCS	[M-2H]-	162.458	30932474
DeepCCS	[M+Na]+	137.194	30932474
AllCCS	[M+H]+	124.6	32859911
AllCCS	[M+H-H2O]+	119.8	32859911
AllCCS	[M+NH4]+	129.0	32859911
AllCCS	[M+Na]+	130.2	32859911
AllCCS	[M-H]-	126.0	32859911
AllCCS	[M+Na-2H]-	128.6	32859911
AllCCS	[M+HCOO]-	131.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-5-methyl-3(2H)-thiophenone	CC1=C(O)C(=O)CS1	2062.7	Standard polar	33892256
4-Hydroxy-5-methyl-3(2H)-thiophenone	CC1=C(O)C(=O)CS1	1126.8	Standard non polar	33892256
4-Hydroxy-5-methyl-3(2H)-thiophenone	CC1=C(O)C(=O)CS1	1171.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-5-methyl-3(2H)-thiophenone,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(=O)CS1	1350.1	Semi standard non polar	33892256
4-Hydroxy-5-methyl-3(2H)-thiophenone,1TMS,isomer #2	CC1=C(O)C(O[Si](C)(C)C)=CS1	1318.0	Semi standard non polar	33892256
4-Hydroxy-5-methyl-3(2H)-thiophenone,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CS1	1365.5	Semi standard non polar	33892256
4-Hydroxy-5-methyl-3(2H)-thiophenone,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CS1	1479.6	Standard non polar	33892256
4-Hydroxy-5-methyl-3(2H)-thiophenone,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)CS1	1602.6	Semi standard non polar	33892256
4-Hydroxy-5-methyl-3(2H)-thiophenone,1TBDMS,isomer #2	CC1=C(O)C(O[Si](C)(C)C(C)(C)C)=CS1	1627.1	Semi standard non polar	33892256
4-Hydroxy-5-methyl-3(2H)-thiophenone,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CS1	1862.0	Semi standard non polar	33892256
4-Hydroxy-5-methyl-3(2H)-thiophenone,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CS1	1895.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-5-methyl-3(2H)-thiophenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9100000000-75159023aa0027152d54	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-5-methyl-3(2H)-thiophenone GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9500000000-203e2e6715cc081fe432	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-5-methyl-3(2H)-thiophenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-5-methyl-3(2H)-thiophenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-5-methyl-3(2H)-thiophenone 10V, Positive-QTOF	splash10-001i-0900000000-f8416206be03640f6904	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-5-methyl-3(2H)-thiophenone 20V, Positive-QTOF	splash10-001i-5900000000-55c167c104b184c3fa13	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-5-methyl-3(2H)-thiophenone 40V, Positive-QTOF	splash10-0c00-9200000000-d1aa3818c3e108fe5e85	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-5-methyl-3(2H)-thiophenone 10V, Negative-QTOF	splash10-004i-7900000000-6dc0c95cbfc888ab6c6f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-5-methyl-3(2H)-thiophenone 20V, Negative-QTOF	splash10-00ai-9200000000-760213afdddc179218f2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-5-methyl-3(2H)-thiophenone 40V, Negative-QTOF	splash10-0kfx-9000000000-97fdb54ebfae4deb81da	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-5-methyl-3(2H)-thiophenone 10V, Positive-QTOF	splash10-001i-0900000000-3abb6b90eca436cd40fa	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-5-methyl-3(2H)-thiophenone 20V, Positive-QTOF	splash10-0pbi-9300000000-d0ba6005462bd6c472a6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-5-methyl-3(2H)-thiophenone 40V, Positive-QTOF	splash10-0a4v-9000000000-1c96e5ff26fb4949efaf	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-5-methyl-3(2H)-thiophenone 10V, Negative-QTOF	splash10-0kmi-9200000000-79c7a2dbd54f2cfb372f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-5-methyl-3(2H)-thiophenone 20V, Negative-QTOF	splash10-001i-9000000000-9cbb1971fa57dadc3c46	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-5-methyl-3(2H)-thiophenone 40V, Negative-QTOF	splash10-053r-9000000000-8fa4783c6c7c8d1d8867	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011612

KNApSAcK ID

Not Available

Chemspider ID

15354200

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22752005

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1836611

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 4-Hydroxy-5-methyl-3(2H)-thiophenone (HMDB0033548)

MOL for HMDB0033548 (4-Hydroxy-5-methyl-3(2H)-thiophenone)

3D MOL for HMDB0033548 (4-Hydroxy-5-methyl-3(2H)-thiophenone)

3D SDF for HMDB0033548 (4-Hydroxy-5-methyl-3(2H)-thiophenone)

3D-SDF for HMDB0033548 (4-Hydroxy-5-methyl-3(2H)-thiophenone)

PDB for HMDB0033548 (4-Hydroxy-5-methyl-3(2H)-thiophenone)

3D PDB for HMDB0033548 (4-Hydroxy-5-methyl-3(2H)-thiophenone)

SMILES for HMDB0033548 (4-Hydroxy-5-methyl-3(2H)-thiophenone)

INCHI for HMDB0033548 (4-Hydroxy-5-methyl-3(2H)-thiophenone)

Structure for HMDB0033548 (4-Hydroxy-5-methyl-3(2H)-thiophenone)

3D Structure for HMDB0033548 (4-Hydroxy-5-methyl-3(2H)-thiophenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra