5-(2-Hydroxyethyl)-4-methylthiazole (YMDB00706)

Identification

YMDB ID

YMDB00706

Name

5-(2-Hydroxyethyl)-4-methylthiazole

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

5-(2-Hydroxyethyl)-4-methylthiazole is a thiazole, a type of nitrogenous heterocycle compound. Thiazoles are found in different processed foods and are the products of the Maillard reaction, which involves an amino acid and a reducing sugar. Thiazoles are volatile compounds responsible for popcorn, roasted, and peanuts aromas. 5-(2-Hydroxyethyl)-4-methylthiazole is also a substrate in thiamin (vitamin B1) biosynthesis. [PMID: 12358442] [Biocyc THISYN-PWY]

Structure

MOL SDF PDB SMILES InChI

Synonyms

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

CAS number

137-00-8

Weight

Average: 143.207
Monoisotopic: 143.040484605

InChI Key

BKAWJIRCKVUVED-UHFFFAOYSA-N

InChI

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

IUPAC Name

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

Traditional IUPAC Name

4-methyl-5-thiazoleethanol

Chemical Formula

C₆H₉NOS

SMILES

CC1=C(CCO)SC=N1

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

Charge

Melting point

< 25 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

cytoplasm

Organoleptic Properties

Flavour/Odour	Source
Cooked beef juice	FDB030512
Fatty	FDB030512
Sulfur	FDB030512

SMPDB Pathways

Vitamin B1/Thiamine metabolism

PW002486

KEGG Pathways

Thiamine metabolism

ec00730

SMPDB Reactions

oxythiamine + water → 5-(2-Hydroxyethyl)-4-methylthiazole + hydron + 5-(hydroxymethyl)-2-methyl-4(1H)-pyrimidinone

5-(2-Hydroxyethyl)-4-methylthiazole + Adenosine triphosphate → 4-methyl-5-(2-phosphonooxyethyl)thiazole + hydron + ADP

KEGG Reactions

Adenosine triphosphate + 5-(2-Hydroxyethyl)-4-methylthiazole → 4-Methyl-5-(2-phosphonooxyethyl)thiazole + hydron + ADP

Thiamine + water → hydron + 4-amino-5-hydroxymethyl-2-methylpyrimidine + 5-(2-Hydroxyethyl)-4-methylthiazole

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0udi-3910000000-2c7da803c60f23e92cb8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-3900000000-373fe84bca11e1b9a8e8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-3910000000-2c7da803c60f23e92cb8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-2910000000-917762a1db7938b1744a	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-5900000000-a533361156b4169f3662	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9320000000-2699a9d0d4585266a9fb	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-0900000000-752807b0316740b2f094	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-0900000000-78f29564099d057faa39	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03di-1900000000-eed8b0468f9906ba231c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03di-3900000000-f44ad5d4a3225d9b0bcc	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03di-9700000000-33a95f67a6613491886d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-01ox-0900000000-06db10539c8be16d6109	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-1900000000-0c0977714e57292d99f9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-03dl-0900000000-88e26c627663843f9708	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-03di-1900000000-0c0977714e57292d99f9	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004l-0900000000-77f0167f1adcb7bd13de	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-1900000000-7716ea7b3c8440649464	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ta-9500000000-67d0defea9e8825ae1aa	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01ox-1900000000-11ac5d4965cdb773ab47	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006w-9600000000-fbed1a518b95bea3510c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-7872cc957fe09907a8b7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004l-0900000000-2e5c326d07e929018d95	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01u3-8900000000-c889afd6f3bb43d37fdb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9100000000-b0bb72c5777ad7b7b1a1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9100000000-b34c758ceec8653ad03f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dl-9300000000-70a6aa386fb75b9d9b36	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-bb4dcf1719345df44077	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Johnson, D. B., Howells, D. J., Goodwin, T. W. (1966). "Observations on the biosynthesis of thiamine in yeast." Biochem J 98:30-37.5938656
Linnett, P. E., Walker, J. (1968). "Biosynthesis of thiamine. Incorporation experiments with 14C-labelled substrates and with (15N)glycine in Saccharomyces cerevisiae." Biochem J 109:161-168.5679359
White, R. L., Spenser, I. D. (1979). "Thiamin biosynthesis in Saccharomyces cerevisiae. Origin of carbon-2 of the thiazole moiety." Biochem J 179:315-325.384994
Boer, V. M., Crutchfield, C. A., Bradley, P. H., Botstein, D., Rabinowitz, J. D. (2010). "Growth-limiting intracellular metabolites in yeast growing under diverse nutrient limitations." Mol Biol Cell 21:198-211.19889834

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	17957
HMDB ID	HMDB0032985
Pubchem Compound ID	1136
Kegg ID	C04294
ChemSpider ID	1104
FOODB ID	FDB030512
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Hydroxymethylpyrimidine/phosphomethylpyrimidine kinase THI20

General function:: Involved in phosphomethylpyrimidine kinase activity
Specific function:: Catalyzes the phosphorylation of hydroxymethylpyrimidine phosphate (HMP-P) to HMP-PP, and also probaby that of HMP to HMP- P
Gene Name:: THI20
Uniprot ID:: Q08224
Molecular weight:: 61268.89844

Reactions

ATP + 4-amino-5-hydroxymethyl-2-methylpyrimidine → ADP + 4-amino-5-phosphonooxymethyl-2-methylpyrimidine.
ATP + 4-amino-2-methyl-5-phosphomethylpyrimidine → ADP + 4-amino-2-methyl-5-diphosphomethylpyrimidine.
thiamine + H2O → 4-amino-5-hydroxymethyl-2-methylpyrimidine + 5-(2-hydroxyethyl)-4-methylthiazole.

Protein Details

2. Thiamine biosynthetic bifunctional enzyme

General function:: Involved in catalytic activity
Specific function:: Essential for thiamine biosynthesis. The kinase activity is involved in the salvage synthesis of TH-P from the thiazole
Gene Name:: THI6
Uniprot ID:: P41835
Molecular weight:: 58058.19922

Reactions

2-methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4-methyl-5-(2-phosphono-oxyethyl)thiazole → diphosphate + thiamine phosphate.
ATP + 4-methyl-5-(2-hydroxyethyl)thiazole → ADP + 4-methyl-5-(2-phosphonooxyethyl)thiazole.

5-(2-Hydroxyethyl)-4-methylthiazole (YMDB00706)

Structure for #<Compound:0xa743b0a0>

Enzymes

Reactions

Reactions