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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:53:49 UTC

Update Date

2023-02-21 17:23:05 UTC

HMDB ID

HMDB0033116

Secondary Accession Numbers

HMDB33116

Metabolite Identification

Common Name

4-Methylthiazole

Description

4-Methylthiazole, also known as fema 3716, belongs to the class of organic compounds known as thiazoles. These are heterocyclic compounds containing a five-member aromatic ring made up of one sulfur atom, one nitrogen, and three carbon atoms. 4-Methylthiazole is a green, nutty, and roasted meat tasting compound. 4-methylthiazole has been detected, but not quantified, in several different foods, such as cereals and cereal products, coffee and coffee products, crustaceans, green vegetables, and nuts. This could make 4-methylthiazole a potential biomarker for the consumption of these foods. 4-Methylthiazole has been linked to the inborn metabolic disorders including celiac disease. A 1,3-thiazole substituted by a methyl group at position 4.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Methyl thiazole	HMDB
4-Methyl-1,3-thiazole	HMDB
4-Methyl-5H-1,3-thiazole	HMDB
FEMA 3716	HMDB

Chemical Formula

C₄H₅NS

Average Molecular Weight

99.154

Monoisotopic Molecular Weight

99.014269855

IUPAC Name

4-methyl-1,3-thiazole

Traditional Name

4-methylthiazole

CAS Registry Number

693-95-8

SMILES

CC1=CSC=N1

InChI Identifier

InChI=1S/C4H5NS/c1-4-2-6-3-5-4/h2-3H,1H3

InChI Key

QMHIMXFNBOYPND-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiazoles. These are heterocyclic compounds containing a five-member aromatic ring made up of one sulfur atom, one nitrogen, and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Thiazoles

Direct Parent

Thiazoles

Alternative Parents

Substituents

Heteroaromatic compound
Thiazole
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1,3-thiazole (CHEBI:35626 )

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0033116)
Cytoplasm (HMDB: HMDB0033116)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0033116)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033116)

Source

Exogenous

Food

Food (HMDB: HMDB0033116)

Vegetable

Shoot vegetable

Asparagus (FooDB: FOOD00021)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Nut

Nuts (FooDB: FOOD00869)

Aquatic origin

Crustacean

Crustaceans (FooDB: FOOD00862)

Endogenous

Plant

Animal

Animal (HMDB: HMDB0033116)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033116)

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0033116)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	133.00 to 134.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	17460 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.97	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.36 g/L	ALOGPS
logP	1.29	ALOGPS
logP	0.76	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Basic)	2.74	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.89 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	25.86 m³·mol⁻¹	ChemAxon
Polarizability	10.1 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
DarkChem	[M+H]+	115.021	31661259
DarkChem	[M-H]-	107.859	31661259
DeepCCS	[M+H]+	120.833	30932474
DeepCCS	[M-H]-	118.902	30932474
DeepCCS	[M-2H]-	154.589	30932474
DeepCCS	[M+Na]+	129.056	30932474
AllCCS	[M+H]+	117.9	32859911
AllCCS	[M+H-H2O]+	112.9	32859911
AllCCS	[M+NH4]+	122.7	32859911
AllCCS	[M+Na]+	124.1	32859911
AllCCS	[M-H]-	122.2	32859911
AllCCS	[M+Na-2H]-	126.0	32859911
AllCCS	[M+HCOO]-	130.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Methylthiazole	CC1=CSC=N1	1255.2	Standard polar	33892256
4-Methylthiazole	CC1=CSC=N1	793.3	Standard non polar	33892256
4-Methylthiazole	CC1=CSC=N1	820.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 4-Methylthiazole EI-B (Non-derivatized)	splash10-00dj-9000000000-6548e81d140752f9aa7b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Methylthiazole EI-B (Non-derivatized)	splash10-00dj-9000000000-6548e81d140752f9aa7b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methylthiazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9000000000-3365a1451133968fdf9d	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methylthiazole 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-Methylthiazole 10V, Positive-QTOF	splash10-0udi-0900000000-93c84d5d0cade8e31a92	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylthiazole 20V, Positive-QTOF	splash10-0udi-1900000000-1ae733c747da10da96ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylthiazole 40V, Positive-QTOF	splash10-0udi-9000000000-e138d70578ebadc8c232	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylthiazole 10V, Negative-QTOF	splash10-0002-9000000000-aff1faf4c9ac4bfa1b3c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylthiazole 20V, Negative-QTOF	splash10-006t-9000000000-58913fe61cdf30c9e090	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylthiazole 40V, Negative-QTOF	splash10-00di-9000000000-8ee31c0c6bade156e5e2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylthiazole 10V, Positive-QTOF	splash10-0udi-0900000000-c6b270500d467d426a6a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylthiazole 20V, Positive-QTOF	splash10-0udi-9400000000-92d8fd57f1e1e12b4be9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylthiazole 40V, Positive-QTOF	splash10-0udi-9000000000-3ba898bdcee1cd9d2a22	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylthiazole 10V, Negative-QTOF	splash10-0a4i-9000000000-0515ac1fa2be4b11f15e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylthiazole 20V, Negative-QTOF	splash10-00xr-9000000000-c404a0405f4a178c1462	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methylthiazole 40V, Negative-QTOF	splash10-006t-9000000000-0363b0e435fe1fb55265	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+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Not Specified	Normal	21970810	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Not Specified	Treated celiac disease	21970810	details

Associated Disorders and Diseases

Disease References

Celiac disease
Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]

Associated OMIM IDs

212750 (Celiac disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011116

KNApSAcK ID

C00016314

Chemspider ID

12224

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12748

PDB ID

Not Available

ChEBI ID

35626

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1037611

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-Methylthiazole (HMDB0033116)

MOL for HMDB0033116 (4-Methylthiazole)

3D MOL for HMDB0033116 (4-Methylthiazole)

3D SDF for HMDB0033116 (4-Methylthiazole)

3D-SDF for HMDB0033116 (4-Methylthiazole)

PDB for HMDB0033116 (4-Methylthiazole)

3D PDB for HMDB0033116 (4-Methylthiazole)

SMILES for HMDB0033116 (4-Methylthiazole)

INCHI for HMDB0033116 (4-Methylthiazole)

Structure for HMDB0033116 (4-Methylthiazole)

3D Structure for HMDB0033116 (4-Methylthiazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra