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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:36:43 UTC

Update Date

2023-02-21 17:27:35 UTC

HMDB ID

HMDB0040069

Secondary Accession Numbers

HMDB40069

Metabolite Identification

Common Name

4-Ethyl-2,5-dimethylthiazole

Description

4-Ethyl-2,5-dimethylthiazole belongs to the class of organic compounds known as 2,4,5-trisubstituted thiazoles. 2,4,5-trisubstituted thiazoles are compounds containing a thiazole ring substituted at positions 2, 4 and 5 only. 4-Ethyl-2,5-dimethylthiazole has been detected, but not quantified in, several different foods, such as mushrooms, potatos (Solanum tuberosum), green tea, teas (Camellia sinensis), and red tea. This could make 4-ethyl-2,5-dimethylthiazole a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Ethyl-2,5-dimethylthiazole.

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,5-Dimethyl-4-ethylthiazole	HMDB
4-Ethyl-2,5-dimethyl-1,3-thiazole	HMDB
4-Ethyl-2,5-dimethyl-thiazole	HMDB

Chemical Formula

C₇H₁₁NS

Average Molecular Weight

141.234

Monoisotopic Molecular Weight

141.061220047

IUPAC Name

4-ethyl-2,5-dimethyl-1,3-thiazole

Traditional Name

4-ethyl-2,5-dimethyl-1,3-thiazole

CAS Registry Number

32272-57-4

SMILES

CCC1=C(C)SC(C)=N1

InChI Identifier

InChI=1S/C7H11NS/c1-4-7-5(2)9-6(3)8-7/h4H2,1-3H3

InChI Key

ZJGXJKFDKNNBTK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,4,5-trisubstituted thiazoles. 2,4,5-Trisubstituted thiazoles are compounds containing a thiazole ring substituted at positions 2, 4 and 5 only.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Thiazoles

Direct Parent

2,4,5-trisubstituted thiazoles

Alternative Parents

Substituents

2,4,5-trisubstituted 1,3-thiazole
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0040069)
Cell membrane (HMDB: HMDB0040069)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040069)

Source

Exogenous

Exogenous (HMDB: HMDB0040069)

Food

Food (HMDB: HMDB0040069)

Vegetable

Mushroom

Tuber

Potato (FooDB: FOOD00175)

Tea

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Endogenous

Plant

Plant (HMDB: HMDB0040069)
Coffea (HMDB: HMDB0040069)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040069)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	115 - 116 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.63 g/L	ALOGPS
logP	2.8	ALOGPS
logP	2.23	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	3.9	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	1	ChemAxon
Refractivity	39.98 m³·mol⁻¹	ChemAxon
Polarizability	16.22 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]+	129.383	31661259
DarkChem	[M-H]-	127.066	31661259
DeepCCS	[M+H]+	141.482	30932474
DeepCCS	[M-H]-	137.684	30932474
DeepCCS	[M-2H]-	174.812	30932474
DeepCCS	[M+Na]+	150.419	30932474
AllCCS	[M+H]+	127.4	32859911
AllCCS	[M+H-H2O]+	123.0	32859911
AllCCS	[M+NH4]+	131.6	32859911
AllCCS	[M+Na]+	132.8	32859911
AllCCS	[M-H]-	132.5	32859911
AllCCS	[M+Na-2H]-	134.7	32859911
AllCCS	[M+HCOO]-	137.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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.	3.57 minutes	32390414
Predicted by Siyang on May 30, 2022	10.2544 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.85 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	39.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	807.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	354.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	124.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	202.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	54.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	303.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	271.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	85.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	780.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	239.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1033.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	256.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	193.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	364.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	323.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	191.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Ethyl-2,5-dimethylthiazole	CCC1=C(C)SC(C)=N1	1425.7	Standard polar	33892256
4-Ethyl-2,5-dimethylthiazole	CCC1=C(C)SC(C)=N1	1051.9	Standard non polar	33892256
4-Ethyl-2,5-dimethylthiazole	CCC1=C(C)SC(C)=N1	1066.4	Semi 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-Ethyl-2,5-dimethylthiazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-3900000000-221948434548f9f21f41	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethyl-2,5-dimethylthiazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ethyl-2,5-dimethylthiazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-7900000000-fcac36367c4cd337a45a	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethylthiazole 10V, Positive-QTOF	splash10-0006-0900000000-a7b8efa0cfa1ed0bd8bb	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethylthiazole 20V, Positive-QTOF	splash10-0006-1900000000-01b1003f6258e11ab48b	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethylthiazole 40V, Positive-QTOF	splash10-00kf-9300000000-5ba1405db2b92c70433c	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethylthiazole 10V, Negative-QTOF	splash10-0006-6900000000-7029a0a94337029b88e6	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethylthiazole 20V, Negative-QTOF	splash10-0006-2900000000-f696cb03a8e8e3c31ed4	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethylthiazole 40V, Negative-QTOF	splash10-0a59-9000000000-ce37c82a6fceb16b0bde	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethylthiazole 10V, Positive-QTOF	splash10-0006-0900000000-0d45245800d32c082056	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethylthiazole 20V, Positive-QTOF	splash10-0006-2900000000-f8d747c742da27ed3d67	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethylthiazole 40V, Positive-QTOF	splash10-07bf-9200000000-042728dd365c51159d04	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethylthiazole 10V, Negative-QTOF	splash10-0006-5900000000-65de1e80fec4ab4a48c1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethylthiazole 20V, Negative-QTOF	splash10-052f-9500000000-c77b036a98065d58a1a9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ethyl-2,5-dimethylthiazole 40V, Negative-QTOF	splash10-0a4i-9000000000-89c3eaed1443a56345bc	2021-09-22	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

Membrane

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

FDB019756

KNApSAcK ID

Not Available

Chemspider ID

33203

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

36098

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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-Ethyl-2,5-dimethylthiazole (HMDB0040069)

MOL for HMDB0040069 (4-Ethyl-2,5-dimethylthiazole)

3D MOL for HMDB0040069 (4-Ethyl-2,5-dimethylthiazole)

3D SDF for HMDB0040069 (4-Ethyl-2,5-dimethylthiazole)

3D-SDF for HMDB0040069 (4-Ethyl-2,5-dimethylthiazole)

PDB for HMDB0040069 (4-Ethyl-2,5-dimethylthiazole)

3D PDB for HMDB0040069 (4-Ethyl-2,5-dimethylthiazole)

SMILES for HMDB0040069 (4-Ethyl-2,5-dimethylthiazole)

INCHI for HMDB0040069 (4-Ethyl-2,5-dimethylthiazole)

Structure for HMDB0040069 (4-Ethyl-2,5-dimethylthiazole)

3D Structure for HMDB0040069 (4-Ethyl-2,5-dimethylthiazole)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra