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4-Methyl-5-(2-phosphonooxyethyl)thiazole (YMDB00319)

Identification
YMDB IDYMDB00319
Name4-Methyl-5-(2-phosphonooxyethyl)thiazole
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description4-Methyl-5-(2-phosphonooxyethyl)thiazole 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. 4-Methyl-5-(2-phosphonooxyethyl)thiazole is also an intermediate in thiamine biosynthesis pathway. [PMID: 12358442] [Biocyc THISYNARA-PWY]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 4-Methyl-5-(2-phosphoethyl)-thiazole
  • 4-Methyl-5-(2-phosphono-oxyethyl)-thiazole
  • 4-methyl-5-(2-phosphonooxyethyl)-thiazole
  • 4-METHYL-5-HYDROXYETHYLTHIAZOLE PHOSPHATE
  • PHOSPHORIC ACID MONO-[2-(4-METHYL-THIAZOL-5-YL)-ETHYL] ESTER
  • 4-Methyl-5-(2-phosphonooxyethyl)thiazole
  • 5-(2-Hydroxyethyl)-4-methylthiazole phosphate
  • HET-p
  • PHOSPHate mono-[2-(4-methyl-thiazol-5-yl)-ethyl] ester
  • 5-(2-Hydroxyethyl)-4-methylthiazole phosphoric acid
  • 4-Methyl-5-hydroxyethylthiazole phosphoric acid
  • 4-Metyl-5-(b-hydroxyethyl)thiazole phosphate
  • 4-Metyl-5-(b-hydroxyethyl)thiazole phosphoric acid
  • 4-Metyl-5-(beta-hydroxyethyl)thiazole phosphoric acid
  • 4-Metyl-5-(β-hydroxyethyl)thiazole phosphate
  • 4-Metyl-5-(β-hydroxyethyl)thiazole phosphoric acid
CAS numberNot Available
WeightAverage: 223.187
Monoisotopic: 223.006815015
InChI KeyOCYMERZCMYJQQO-UHFFFAOYSA-N
InChIInChI=1S/C6H10NO4PS/c1-5-6(13-4-7-5)2-3-11-12(8,9)10/h4H,2-3H2,1H3,(H2,8,9,10)
IUPAC Name[2-(4-methyl-1,3-thiazol-5-yl)ethoxy]phosphonic acid
Traditional IUPAC Name2-(4-methyl-1,3-thiazol-5-yl)ethoxyphosphonic acid
Chemical FormulaC6H10NO4PS
SMILESCC1=C(CCOP(O)(O)=O)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
  • Monoalkyl phosphate
  • 4,5-disubstituted 1,3-thiazole
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.73 g/LALOGPS
logP0.09ALOGPS
logP-0.51ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.61ChemAxon
pKa (Strongest Basic)2.58ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.65 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity48.2 m³·mol⁻¹ChemAxon
Polarizability19.25 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Vitamin B1/Thiamine metabolismPW002486 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Thiamine metabolismec00730 Map00730
SMPDB ReactionsNot Available
KEGG Reactions
Adenosine triphosphate + 5-(2-Hydroxyethyl)-4-methylthiazole → 4-Methyl-5-(2-phosphonooxyethyl)thiazole + hydron + ADP
4-Methyl-5-(2-phosphonooxyethyl)thiazole + hydron + 4-amino-2-methyl-5-diphosphomethylpyrimidine → Pyrophosphate + Thiamine monophosphate
Glycine + alpha-D-ribose 5-phosphate + hydron + L-Cysteine + O-Acetyl-L-homoserine → Pyruvic acid + Acetic acid + Carbon dioxide + gamma-Aminobutyric acid + 4-Methyl-5-(2-phosphonooxyethyl)thiazole + Ammonium + water
Glycine + hydron + L-Cysteine + Xylulose 5-phosphate + O-Acetyl-L-homoserine → Pyruvic acid + Acetic acid + Carbon dioxide + gamma-Aminobutyric acid + 4-Methyl-5-(2-phosphonooxyethyl)thiazole + Ammonium + water
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9300000000-4b265fbb33f5d2a284a5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00fr-1970000000-6d53ae2ae5cf22f5c35dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1900000000-2a7dfc383c0b8f0bc737JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ta-8900000000-f80f35678c9e0a53bfdfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-9170000000-0f15ea5b2875cc1966c8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-9be355f278967310c343JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-3af10cdc8386468900f8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00fr-0690000000-c5a85288f3c0ae83b359JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-4900000000-5a3ba3a8afe5cee644b5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03gi-9600000000-47caa828201211845c2bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fs-9050000000-392915fcb08678ef8065JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17857
HMDB IDHMDB0304185
Pubchem Compound ID25245616
Kegg IDC04327
ChemSpider ID1105
FOODB IDFDB030511
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. 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.