NP-MRD: Showing NP-Card for 5-(2-Hydroxyethyl)-4-methylthiazole (NP0001247)

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Record Information

Version

1.0

Created at

2012-09-11 17:53:05 UTC

Updated at

2021-08-19 23:58:57 UTC

NP-MRD ID

NP0001247

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(2-Hydroxyethyl)-4-methylthiazole

Description

5-(2-Hydroxyethyl)-4-methylthiazole, also known as 4-methyl-5-(2'-hydroxyethyl)-thiazole or 4-methyl-5-thiazolethanol, belongs to the class of organic compounds known as 4,5-disubstituted thiazoles. 4,5-Disubstituted thiazoles are compounds containing a thiazole ring substituted at positions 4 and 5 only. 5-(2-Hydroxyethyl)-4-methylthiazole exists in all living species, ranging from bacteria to humans. 5-(2-Hydroxyethyl)-4-methylthiazole is a sulfur tasting compound. 5-(2-Hydroxyethyl)-4-methylthiazole has been detected, but not quantified, in several different foods, such as kohlrabis, red bell peppers, citrus, avocado, and black-eyed pea. This could make 5-(2-hydroxyethyl)-4-methylthiazole a potential biomarker for the consumption of these foods. A 1,3-thiazole that is thiazole substituted by a methyl group at position 4 and a 2-hydroxyethyl group at position 5.

Structure

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

View in JSmol View NMR Assignments

Synonyms

Value	Source
4-Methyl-5-(2'-hydroxyethyl)-thiazole	ChEBI
4-Methyl-5-(2-hydroxyethyl)-thiazole	ChEBI
4-Methyl-5-thiazolethanol	ChEBI
Hemineurine	ChEBI
4-Methyl-5-(2-hydroxyethyl)thiazole	Kegg
HET	Kegg
2-(4-Methyl-1,3-thiazol-5-yl)ethanol	HMDB
2-(4-Methyl-5-thiazolyl)ethanol	HMDB
2-(4-METHYL-thiazol-5-yl)-ethanol	HMDB
2-(4-Methylthiazol-5-yl)ethanol	HMDB
2-(4-Methylthiazole-5-yl)ethanol	HMDB
4-METHYL-5-(beta-hydroxyethyl)-thiazole	HMDB
4-Methyl-5-(beta-hydroxyethyl)thiazole	HMDB
4-Methyl-5-hydroxethylthiazole	HMDB
4-Methyl-5-hydroxyethylthiazole	HMDB
4-Methyl-5-thiazoleethanol	HMDB
4-Methyl-5-thiazoleethanol, 9ci	HMDB
4-Methyl-5-thiazolylethanol	HMDB
4-Metyl-5-(beta-hydroxyethyl)thiazole	HMDB
5-(2-Hydroxyethyl)-4-methylthiazole (sulfurol)	HMDB
5-(beta-Hydroxyethyl)-4-methylthiazole	HMDB
5-(Hydroxyethyl)-4-methylthiazole	HMDB
FEMA 3204	HMDB
MHT	HMDB
Sulfurol	HMDB
Thiamine breakdown product 4-methyl-5-thiazoleethanol- from	HMDB
Thiamine thiazole	HMDB
Thiazole, 5-(2-hydroxyethyl)-4-methyl	HMDB
TZE	HMDB
Thiamine thiazole hydrochloride	HMDB
Thiamine thiazole phosphate	HMDB
4-Methyl-5-(2-thiazoleethanol)	HMDB
4-Methyl-5-(β-hydroxyethyl)thiazole	HMDB
5-(Β-hydroxyethyl)-4-methylthiazole	HMDB
THZ	HMDB
5-(2-Hydroxyethyl)-4-methylthiazole	MeSH

Chemical Formula

C₆H₉NOS

Average Mass

143.2070 Da

Monoisotopic Mass

143.04048 Da

IUPAC Name

2-(4-methyl-1,3-thiazol-5-yl)ethan-1-ol

Traditional Name

4-methyl-5-thiazoleethanol

CAS Registry Number

137-00-8

SMILES

CC1=C(CCO)SC=N1

InChI Identifier

InChI=1S/C6H9NOS/c1-5-6(2-3-8)9-4-7-5/h4,8H,2-3H2,1H3

InChI Key

BKAWJIRCKVUVED-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Brassica napus	KNApSAcK Database	22123792
Panax ginseng	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Boletus edulis	KNApSAcK Database	22123792
Escherichia coli K12	KNApSAcK Database	22123792

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Thiazoles

Direct Parent

4,5-disubstituted thiazoles

Alternative Parents

Substituents

4,5-disubstituted 1,3-thiazole
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1,3-thiazole (CHEBI:17957 )
primary alcohol (CHEBI:17957 )
Thiazole alkaloids (C04294 )
a thiazole (THZ )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	135.00 °C. @ 7.00 mm Hg	The Good Scents Company Information System
Water Solubility	9081 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.275 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
Water Solubility	2.26 g/L	ALOGPS
logP	0.67	ALOGPS
logP	0.42	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	15.62	ChemAxon
pKa (Strongest Basic)	3.12	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	33.12 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	37.32 m³·mol⁻¹	ChemAxon
Polarizability	14.92 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

External Links

HMDB ID

HMDB0032985

DrugBank ID

DB02969

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

PDB ID

ChEBI ID

Good Scents ID

References

General References

Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
Ende M, Spiteller G, Remberg G, Heipertz R: Urinary metabolites of clomethiazole. Detection and structural analysis by gas chromatography-mass spectrometry. Arzneimittelforschung. 1979;29(11):1655-8. [PubMed:543872 ]
Song Z, Pan J, Xie L, Gong G, Han S, Zhang W, Hu Y: Expression, Purification, and Activity of ActhiS, a Thiazole Biosynthesis Enzyme from Acremonium chrysogenum. Biochemistry (Mosc). 2017 Jul;82(7):852-860. doi: 10.1134/S0006297917070112. [PubMed:28918750 ]
Mo S, Luo HQ, Li NB: Study on the influences of two thiazole flavor ingredients on Cu corrosion caused by chloride ion. J Colloid Interface Sci. 2017 Nov 1;505:929-939. doi: 10.1016/j.jcis.2017.06.075. Epub 2017 Jun 23. [PubMed:28675872 ]
Kijima Y, Hayashi M, Yamada K, Tazuya-Murayama K: The Biosynthesis of the Pyrimidine Moiety of Thiamin in Halobacterium salinarum. J Nutr Sci Vitaminol (Tokyo). 2016;62(2):130-3. doi: 10.3177/jnsv.62.130. [PubMed:27264098 ]
Hayashi M, Kijima Y, Tazuya-Murayama K, Yamada K: The Biosynthesis of the Thiazole Moiety of Thiamin in the Archaeon Halobacterium salinarum. J Nutr Sci Vitaminol (Tokyo). 2015;61(3):270-4. doi: 10.3177/jnsv.61.270. [PubMed:26226965 ]
Begum A, Drebes J, Kikhney A, Muller IB, Perbandt M, Svergun D, Wrenger C, Betzel C: Staphylococcus aureus thiaminase II: oligomerization warrants proteolytic protection against serine proteases. Acta Crystallogr D Biol Crystallogr. 2013 Dec;69(Pt 12):2320-9. doi: 10.1107/S0907444913021550. Epub 2013 Nov 19. [PubMed:24311574 ]
Begum A, Drebes J, Perbandt M, Wrenger C, Betzel C: Purification, crystallization and preliminary X-ray diffraction analysis of the thiaminase type II from Staphylococcus aureus. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2011 Jan 1;67(Pt 1):51-3. doi: 10.1107/S1744309110043174. Epub 2010 Dec 21. [PubMed:21206023 ]
Fedrizzi B, Magno F, Finato F, Versini G: Variation of some fermentative sulfur compounds in Italian "millesime" classic sparkling wines during aging and storage on lees. J Agric Food Chem. 2010 Sep 8;58(17):9716-22. doi: 10.1021/jf101478w. [PubMed:20806972 ]
Muller IB, Bergmann B, Groves MR, Couto I, Amaral L, Begley TP, Walter RD, Wrenger C: The vitamin B1 metabolism of Staphylococcus aureus is controlled at enzymatic and transcriptional levels. PLoS One. 2009 Nov 3;4(11):e7656. doi: 10.1371/journal.pone.0007656. [PubMed:19888457 ]
Kowalska E, Kozik A: The genes and enzymes involved in the biosynthesis of thiamin and thiamin diphosphate in yeasts. Cell Mol Biol Lett. 2008;13(2):271-82. doi: 10.2478/s11658-007-0055-5. Epub 2008 Apr 10. [PubMed:18161008 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing NP-Card for 5-(2-Hydroxyethyl)-4-methylthiazole (NP0001247)

MOL for NP0001247 (5-(2-Hydroxyethyl)-4-methylthiazole)

3D MOL for NP0001247 (5-(2-Hydroxyethyl)-4-methylthiazole)

3D SDF for NP0001247 (5-(2-Hydroxyethyl)-4-methylthiazole)

3D-SDF for NP0001247 (5-(2-Hydroxyethyl)-4-methylthiazole)

PDB for NP0001247 (5-(2-Hydroxyethyl)-4-methylthiazole)

3D PDB for NP0001247 (5-(2-Hydroxyethyl)-4-methylthiazole)

SMILES for NP0001247 (5-(2-Hydroxyethyl)-4-methylthiazole)

INCHI for NP0001247 (5-(2-Hydroxyethyl)-4-methylthiazole)

Structure for NP0001247 (5-(2-Hydroxyethyl)-4-methylthiazole)

3D Structure for NP0001247 (5-(2-Hydroxyethyl)-4-methylthiazole)