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Identification
YMDB IDYMDB00706
Name5-(2-Hydroxyethyl)-4-methylthiazole
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description5-(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
Thumb
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 number137-00-8
WeightAverage: 143.207
Monoisotopic: 143.040484605
InChI KeyBKAWJIRCKVUVED-UHFFFAOYSA-N
InChIInChI=1S/C6H9NOS/c1-5-6(2-3-8)9-4-7-5/h4,8H,2-3H2,1H3
IUPAC Name2-(4-methyl-1,3-thiazol-5-yl)ethan-1-ol
Traditional IUPAC Name4-methyl-5-thiazoleethanol
Chemical FormulaC6H9NOS
SMILESCC1=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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassThiazoles
Direct Parent4,5-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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point< 25 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.26 g/LALOGPS
logP0.67ALOGPS
logP0.42ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)15.62ChemAxon
pKa (Strongest Basic)3.12ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area33.12 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.32 m³·mol⁻¹ChemAxon
Polarizability14.92 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
Cooked beef juiceFDB030512
FattyFDB030512
SulfurFDB030512
SMPDB Pathways
Vitamin B1/Thiamine metabolismPW002486 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Thiamine metabolismec00730 Map00730
SMPDB Reactions
oxythiamine + water5-(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-methylthiazole4-Methyl-5-(2-phosphonooxyethyl)thiazole + hydron + ADP
Thiamine + waterhydron + 4-amino-5-hydroxymethyl-2-methylpyrimidine + 5-(2-Hydroxyethyl)-4-methylthiazole
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0udi-3910000000-2c7da803c60f23e92cb8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-3900000000-373fe84bca11e1b9a8e8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-3910000000-2c7da803c60f23e92cb8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-2910000000-917762a1db7938b1744aJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-5900000000-a533361156b4169f3662JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9320000000-2699a9d0d4585266a9fbJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-752807b0316740b2f094JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-78f29564099d057faa39JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-1900000000-eed8b0468f9906ba231cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-3900000000-f44ad5d4a3225d9b0bccJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-9700000000-33a95f67a6613491886dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01ox-0900000000-06db10539c8be16d6109JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-1900000000-0c0977714e57292d99f9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0900000000-77f0167f1adcb7bd13deJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1900000000-7716ea7b3c8440649464JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ta-9500000000-67d0defea9e8825ae1aaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ox-1900000000-11ac5d4965cdb773ab47JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006w-9600000000-fbed1a518b95bea3510cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-7872cc957fe09907a8b7JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
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:
ResourceLink
CHEBI ID17957
HMDB IDHMDB0032985
Pubchem Compound ID1136
Kegg IDC04294
ChemSpider ID1104
FOODB IDFDB030512
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

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.
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.