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

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
MOLSDFPDBSMILESInChI
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 + 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 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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
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
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03dl-0900000000-88e26c627663843f9708JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0900000000-2e5c326d07e929018d95JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01u3-8900000000-c889afd6f3bb43d37fdbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9100000000-b0bb72c5777ad7b7b1a1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9100000000-b34c758ceec8653ad03fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-9300000000-70a6aa386fb75b9d9b36JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-bb4dcf1719345df44077JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
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

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.