4-Methyl-5-(2-phosphoethyl)-thiazole (ECMDB20094) (M2MDB000942)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 14:27:09 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-06-03 17:19:18 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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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 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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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 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 |
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Molecular Framework | Aromatic heteromonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Adenosine triphosphate + Dehydroglycine + 1-Deoxy-D-xylulose 5-phosphate + Hydrogen ion + IscS with bound sulfur + NADPH > 4-Methyl-5-(2-phosphoethyl)-thiazole + Adenosine monophosphate + Carbon dioxide +2 Water + IscS sulfur acceptor protein + NADP + Pyrophosphate 5-(2-Hydroxyethyl)-4-methylthiazole + Adenosine triphosphate + 4-methyl-5-(2-hydroxyethyl)thiazole <> 4-Methyl-5-(2-phosphoethyl)-thiazole + ADP + Hydrogen ion 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4-Methyl-5-(2-phosphoethyl)-thiazole + Hydrogen ion <> Pyrophosphate + Thiamine monophosphate 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4-Methyl-5-(2-phosphoethyl)-thiazole <> Pyrophosphate + Thiamine monophosphate Adenosine triphosphate + 5-(2-Hydroxyethyl)-4-methylthiazole <> ADP + 4-Methyl-5-(2-phosphoethyl)-thiazole C15815 + L-Tyrosine + Iminoglycine <> 4-Methyl-5-(2-phosphoethyl)-thiazole Hydrogen ion + 4-Methyl-5-(2-phosphoethyl)-thiazole + 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate > Thiamine monophosphate + Pyrophosphate Adenosine triphosphate + 5-(2-Hydroxyethyl)-4-methylthiazole > Hydrogen ion + ADP + 4-Methyl-5-(2-phosphoethyl)-thiazole 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4-Methyl-5-(2-phosphoethyl)-thiazole > Pyrophosphate + Thiamine monophosphate C15815 + L-Tyrosine + 2-iminoacetate <>4 4-Methyl-5-(2-phosphoethyl)-thiazole 2 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4 4-Methyl-5-(2-phosphoethyl)-thiazole + Hydrogen ion <> Pyrophosphate + Thiamine monophosphate C15815 + L-Tyrosine + 2-iminoacetate <>4 4-Methyl-5-(2-phosphoethyl)-thiazole | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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External Links: |
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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(+). |