Record Information
Version2.0
Creation Date2012-05-31 14:27:09 -0600
Update Date2015-06-03 17:19:18 -0600
Secondary Accession Numbers
  • ECMDB20094
Identification
Name:4-Methyl-5-(2-phosphoethyl)-thiazole
Description:4-methyl-5-(2-phosphoethyl)-thiazole is a member of the chemical class known as Organophosphate Esters. These are organic compounds containing phosphoric acid ester functional group.
Structure
Thumb
Synonyms:
  • 2-(4-Methyl-1,3-thiazol-5-yl)ethyl dihydrogen phosphate
  • 2-(4-Methyl-1,3-thiazol-5-yl)ethyl dihydrogen phosphoric acid
  • 4-4-Methyl-5-(2-phosphonooxyethyl)-thiazole
  • 4-methyl-5-(β-hydroxyethyl)thiazole phosphate
  • 4-Methyl-5-(β-hydroxyethyl)thiazole phosphoric acid
  • 4-methyl-5-(2-phosphoethyl)-thiazole
  • 4-Methyl-5-(2-phosphono-oxyethyl)-thiazole
  • 4-Methyl-5-(2-phosphonooxyethyl)-thiazole
  • 4-Methyl-5-(2-phosphonooxyethyl)thiazole
  • 4-Methyl-5-(b-hydroxyethyl)thiazole phosphate
  • 4-Methyl-5-(b-hydroxyethyl)thiazole phosphoric acid
  • 4-Methyl-5-(beta-hydroxyethyl)thiazole phosphate
  • 4-Methyl-5-(beta-hydroxyethyl)thiazole phosphoric acid
  • 4-Methyl-5-(β-hydroxyethyl)thiazole phosphate
  • 4-Methyl-5-(β-hydroxyethyl)thiazole phosphoric acid
  • 4-Methyl-5-Hydroxyethylthiazole Phosphate
  • 4-Methyl-5-hydroxyethylthiazole phosphoric acid
  • THQ
  • THZ-p
  • TZP
Chemical Formula:C6H10NO4PS
Weight:Average: 223.187
Monoisotopic: 223.006815015
InChI Key:BAAGZOYOQNMHKY-UHFFFAOYSA-N
InChI:InChI=1S/C6H10NO4PS/c1-4-5(13-3-7-4)2-6(8)12(9,10)11/h3,6,8H,2H2,1H3,(H2,9,10,11)
CAS number:Not Available
IUPAC Name:[1-hydroxy-2-(4-methyl-1,3-thiazol-5-yl)ethyl]phosphonic acid
Traditional IUPAC Name:1-hydroxy-2-(4-methyl-1,3-thiazol-5-yl)ethylphosphonic acid
SMILES:CC1=C(CC(O)P(O)(O)=O)SC=N1
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as 4,5-disubstituted thiazoles. These are compounds containing a thiazole ring substituted at positions 4 and 5 only.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassAzoles
Direct Parent4,5-disubstituted thiazoles
Alternative Parents
Substituents
  • 4,5-disubstituted 1,3-thiazole
  • Heteroaromatic compound
  • Organophosphonic acid derivative
  • Organophosphonic acid
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organophosphorus compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility3.35 mg/mLALOGPS
logP-0.44ALOGPS
logP-2ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.26ChemAxon
pKa (Strongest Basic)2.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.65 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.32 m3·mol-1ChemAxon
Polarizability19.21 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0290000000-49b2f96ba724ad894125View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9630000000-5f58842e96106e67e2f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9400000000-3c7e419b92549bd71e64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-3290000000-a031cd9d82030e654164View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-9310000000-b32ab53d9c6a64f1b6dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-9000000000-7a5b0f5a6d20ed12bde3View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17857
HMDB IDNot Available
Pubchem Compound ID1137
Kegg IDC04327
ChemSpider ID1105
Wikipedia IDNot Available
BioCyc IDTHZ-P
EcoCyc IDTHZ-P

Enzymes

General function:
Involved in metabolic process
Specific function:
Catalyzes the removal of elemental sulfur and selenium atoms from cysteine and selenocysteine to produce alanine. Functions as a sulfur delivery protein for NAD, biotin and Fe-S cluster synthesis. Transfers sulfur on 'Cys-456' of thiI in a transpersulfidation reaction. Transfers sulfur on 'Cys-19' of tusA in a transpersulfidation reaction. Functions also as a selenium delivery protein in the pathway for the biosynthesis of selenophosphate
Gene Name:
iscS
Uniprot ID:
P0A6B7
Molecular weight:
45089
Reactions
L-cysteine + acceptor = L-alanine + S-sulfanyl-acceptor.
General function:
Involved in catalytic activity
Specific function:
Condenses 4-methyl-5-(beta-hydroxyethyl)thiazole monophosphate (THZ-P) and 2-methyl-4-amino-5-hydroxymethyl pyrimidine pyrophosphate (HMP-PP) to form thiamine monophosphate (TMP)
Gene Name:
thiE
Uniprot ID:
P30137
Molecular weight:
23015
Reactions
2-methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4-methyl-5-(2-phosphono-oxyethyl)thiazole = diphosphate + thiamine phosphate.
General function:
Involved in hydroxyethylthiazole kinase activity
Specific function:
ATP + 4-methyl-5-(2-hydroxyethyl)thiazole = ADP + 4-methyl-5-(2-phosphonooxyethyl)thiazole
Gene Name:
thiM
Uniprot ID:
P76423
Molecular weight:
27339
Reactions
ATP + 4-methyl-5-(2-hydroxyethyl)thiazole = ADP + 4-methyl-5-(2-phosphonooxyethyl)thiazole.
General function:
Involved in nucleotide binding
Specific function:
Catalyzes the adenylation by ATP of the carboxyl group of the C-terminal glycine of sulfur carrier protein ThiS
Gene Name:
thiF
Uniprot ID:
P30138
Molecular weight:
26970
Reactions
ATP + [ThiS] = diphosphate + adenylyl-[ThiS].
General function:
Involved in RNA binding
Specific function:
Catalyzes the ATP-dependent transfer of a sulfur to tRNA to produce 4-thiouridine in position 8 of tRNAs, which functions as a near-UV photosensor. Also catalyzes the transfer of sulfur to the sulfur carrier protein ThiS, forming ThiS-thiocarboxylate. This is a step in the synthesis of thiazole, in the thiamine biosynthesis pathway. The sulfur is donated as persulfide by iscS
Gene Name:
thiI
Uniprot ID:
P77718
Molecular weight:
54973
Reactions
L-cysteine + 'activated' tRNA = L-serine + tRNA containing a thionucleotide.
[IscS]-SSH + [ThiS]-COAMP = [IscS]-SH + [ThiS]-COSH + AMP.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the rearrangement of 1-deoxy-D-xylulose 5- phosphate (DXP) to produce the thiazole phosphate moiety of thiamine. Sulfur is provided by the thiocarboxylate moiety of the carrier protein ThiS. In vitro, sulfur can be provided by H(2)S
Gene Name:
thiG
Uniprot ID:
P30139
Molecular weight:
26896
Reactions
1-deoxy-D-xylulose 5-phosphate + 2-iminoacetate + thiocarboxy-adenylate-[sulfur-carrier protein ThiS] = 2-((2R,5Z)-2-carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate + [sulfur-carrier protein ThiS] + 2 H(2)O.
General function:
Coenzyme transport and metabolism
Specific function:
Is the sulfur donor in the synthesis of the thiazole phosphate moiety of thiamine phosphate
Gene Name:
thiS
Uniprot ID:
O32583
Molecular weight:
7311
General function:
Involved in catalytic activity
Specific function:
Catalyzes the radical-mediated cleavage of tyrosine to dehydroglycine and p-cresol
Gene Name:
thiH
Uniprot ID:
P30140
Molecular weight:
43320
Reactions
L-tyrosine + S-adenosyl-L-methionine + reduced acceptor = 2-iminoacetate + 4-methylphenol + 5'-deoxyadenosine + L-methionine + acceptor + 2 H(+).