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Record Information
Version	2.0
Creation Date	2012-10-10 12:14:12 -0600
Update Date	2015-06-03 17:25:49 -0600
Secondary Accession Numbers	ECMDB23053
Identification
Name:	2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate
Description	2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate is an intermediate involved in thiamine diphosphate biosynthesis. Thiamine diphosphate, also known as vitamin B1, is known to play a fundamental role in energy metabolism. It is an essential cofactor for a variety of enzymes such as transketolase, pyruvate dehydrogenase, pyruvate decarboxylase, and alpha-ketoglutarate dehydrogenase. Thiamine is synthesized de novo by microorganisms, plants and some lower eukaryotes (e.g. Plasmodium), but not by higher eukaryotes, which must obtain it through their diet.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xaf63bf8c> Close
Synonyms:	(5Z)-4-Methyl-5-(2-phosphonatooxyethylidene)-2H-1,3-thiazole-2-carboxylate (5Z)-4-Methyl-5-(2-phosphonatooxyethylidene)-2H-1,3-thiazole-2-carboxylic acid (R,Z)-2-(2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate (R,Z)-2-(2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphoric acid 2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphoric acid CThz*-P Thiazole tautomer
Chemical Formula:	C7H7NO6PS
Weight:	Average: 264.172 Monoisotopic: 263.973169163
InChI Key:	PQMCQNOVNFNPFJ-DJWKRKHSSA-K
InChI:	InChI=1S/C7H10NO6PS/c1-4-5(2-3-14-15(11,12)13)16-6(8-4)7(9)10/h2,6H,3H2,1H3,(H,9,10)(H2,11,12,13)/p-3/b5-2-
CAS number:	Not Available
IUPAC Name:	(5Z)-4-methyl-5-[2-(phosphonatooxy)ethylidene]-2,5-dihydro-1,3-thiazole-2-carboxylate
Traditional IUPAC Name:	(5Z)-4-methyl-5-[2-(phosphonatooxy)ethylidene]-2H-1,3-thiazole-2-carboxylate
SMILES:	[H]\C(COP([O-])([O-])=O)=C1\SC(N=C1C)C([O-])=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Amino acids, peptides, and analogues
Direct Parent	Alpha amino acids and derivatives
Alternative Parents	Thiazolecarboxylic acids and derivatives Alkyl phosphates Thiazolines Thioenol ethers Ketimines Monocarboxylic acids and derivatives Carboxylic acids Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds Organic anions
Substituents	Alpha-amino acid or derivatives Thiazolecarboxylic acid or derivatives Alkyl phosphate Phosphoric acid ester Organic phosphoric acid derivative Meta-thiazoline Thiazole Thioenolether Ketimine Azacycle Organoheterocyclic compound Monocarboxylic acid or derivatives Carboxylic acid Organic nitrogen compound Organic oxygen compound Organopnictogen compound Organic oxide Hydrocarbon derivative Organooxygen compound Organonitrogen compound Imine Carbonyl group Organic anion Aliphatic heteromonocyclic compound
Molecular Framework	Aliphatic heteromonocyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 26.5 g/L ALOGPS logP 0.52 ALOGPS logP -0.31 ChemAxon logS -1.1 ALOGPS pKa (Strongest Acidic) 1.67 ChemAxon pKa (Strongest Basic) 0.31 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 124.91 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 66.63 m³·mol⁻¹ ChemAxon Polarizability 21.87 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
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 Water 4-amino-2-methyl-5-diphosphomethylpyrimidine + 2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate + 2 Hydrogen ion + 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate > Thiamine monophosphate + Carbon dioxide + diphosphate + Thiamine monophosphate + Pyrophosphate 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate + Hydrogen ion > Carbon dioxide + Pyrophosphate + Thiamine monophosphate 1-Deoxy-D-xylulose 5-phosphate + Dehydroglycine + a thiocarboxy-[ThiS-Protein] > 2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate + a ThiS sulfur-carrier protein +2 Water
SMPDB Pathways:	Thiamin diphosphate biosynthesis PW002028 Thiazole Biosynthesis I PW002041 Vitamin B1/Thiamine PW000892
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-03di-0090000000-5fa092b3be7a77455418 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-08i0-0490000000-06b6cebfee5c4e2d5c79 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0005-9400000000-1e8ab834145bed1e26ec View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03di-1190000000-6641d94d92d2d80c99c5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-03di-5090000000-d7626709d04c13dcc86c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-000i-9000000000-e8812202b947d2d2d123 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Not Available
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID Not Available HMDB ID Not Available Pubchem Compound ID 90659326 Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available

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