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154-87-0,MFCD00038740
Catalog No.:AA00AK0S

154-87-0 | 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium chloride

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1g
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in stock  
$28.00   $20.00
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5g
98%
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$81.00   $57.00
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100g
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$1,094.00   $766.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00AK0S
Chemical Name:
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium chloride
CAS Number:
154-87-0
Molecular Formula:
C12H19ClN4O7P2S
Molecular Weight:
460.7674
MDL Number:
MFCD00038740
SMILES:
Cc1ncc(c(n1)N)C[n+]1csc(c1C)CCOP(=O)(OP(=O)(O)O)O.[Cl-]
Properties
Computed Properties
 
Complexity:
568  
Covalently-Bonded Unit Count:
2  
Heavy Atom Count:
27  
Hydrogen Bond Acceptor Count:
12  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
8  

Downstream Synthesis Route

[1]JustusLiebigsAnnalenderChemie,1958,vol.618,p.210,215,219

[1]Lohmann;Schuster[BiochemischeZeitschrift,1937,vol.294,p.188,199]Karrer;Viscontini[HelveticaChimicaActa,1946,vol.29,p.711,715]

154-87-0   
3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-4-methyl-5-(2-phosphonooxy-ethyl)-thiazolium;iodide 

[1]Lohmann;Schuster[BiochemischeZeitschrift,1937,vol.294,p.188,199]Karrer;Viscontini[HelveticaChimicaActa,1946,vol.29,p.711,715]

154-87-0   
3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-4-methyl-5-(2-phosphonooxy-ethyl)-thiazolium;dihydrogenphosphate 

[1]Lohmann;Schuster[BiochemischeZeitschrift,1937,vol.294,p.188,199]Karrer;Viscontini[HelveticaChimicaActa,1946,vol.29,p.711,715]

154-87-0   
3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-4-methyl-5-(2-phosphonooxy-ethyl)-thiazolium;fluoride-dihydrofluoride 

[1]Lohmann;Schuster[BiochemischeZeitschrift,1937,vol.294,p.188,199]Karrer;Viscontini[HelveticaChimicaActa,1946,vol.29,p.711,715]

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Title: The electrochemical investigation of the catalytic power of pyruvate decarboxylase and its coenzyme.

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Title: Flexibility of thiamine diphosphate revealed by kinetic crystallographic studies of the reaction of pyruvate-ferredoxin oxidoreductase with pyruvate.

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Title: A versatile conformational switch regulates reactivity in human branched-chain alpha-ketoacid dehydrogenase.

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Title: Inclusion of thiamine diphosphate and S-adenosylmethionine at their chemically active sites.

Journal: The Journal of organic chemistry 20051209

Title: The relationship between plasma and red cell B-vitamin concentrations in critically-ill patients.

Journal: Clinical nutrition (Edinburgh, Scotland) 20051201

Title: Structure and mechanism of the ThDP-dependent benzaldehyde lyase from Pseudomonas fluorescens.

Journal: The FEBS journal 20051201

Title: Thiamine pyrophosphate riboswitches are targets for the antimicrobial compound pyrithiamine.

Journal: Chemistry & biology 20051201

Title: Cofactor activation and substrate binding in pyruvate decarboxylase. Insights into the reaction mechanism from molecular dynamics simulations.

Journal: Biochemistry 20051115

Title: Radical phosphate transfer mechanism for the thiamin diphosphate- and FAD-dependent pyruvate oxidase from Lactobacillus plantarum. Kinetic coupling of intercofactor electron transfer with phosphate transfer to acetyl-thiamin diphosphate via a transient FAD semiquinone/hydroxyethyl-ThDP radical pair.

Journal: Biochemistry 20051011

Title: Genetic regulation mediated by thiamin pyrophosphate-binding motif in Saccharomyces cerevisiae.

Journal: Molecular microbiology 20051001

Title: Modification of thiamine pyrophosphate dependent enzyme activity by oxythiamine in Saccharomyces cerevisiae cells.

Journal: Canadian journal of microbiology 20051001

Title: Multiple modes of active center communication in thiamin diphosphate-dependent enzymes.

Journal: Accounts of chemical research 20050901

Title: Topological analysis of the electron density in model azolium systems for thiamin structure-function: sulfur is the electron sink and positively polarized carbanions act as nucleophiles.

Journal: The journal of physical chemistry. A 20050825

Title: The analysis of thiamin and its derivatives in whole blood samples under high pH conditions of the mobile phase.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050805

Title: Studies on thiamine diphosphate-dependent enzymes.

Journal: Biochemical Society transactions 20050801

Title: The potential role of thiamine (vitamin B1) in diabetic complications.

Journal: Current diabetes reviews 20050801

Title: Exchanging the substrate specificities of pyruvate decarboxylase from Zymomonas mobilis and benzoylformate decarboxylase from Pseudomonas putida.

Journal: Protein engineering, design & selection : PEDS 20050701

Title: Binding of the coenzyme and formation of the transketolase active center.

Journal: IUBMB life 20050701

Title: Effect of transketolase substrates on holoenzyme reconstitution and stability.

Journal: Biochemistry. Biokhimiia 20050701

Title: Kinetic control of thiamin diphosphate activation in enzymes studied by proton-nitrogen correlated NMR spectroscopy.

Journal: Biochemistry 20050621

Title: Glutamate 636 of the Escherichia coli pyruvate dehydrogenase-E1 participates in active center communication and behaves as an engineered acetolactate synthase with unusual stereoselectivity.

Journal: The Journal of biological chemistry 20050603

Title: Experimental observation of thiamin diphosphate-bound intermediates on enzymes and mechanistic information derived from these observations.

Journal: Bioorganic chemistry 20050601

Title: Roles of Mg2+ in TPP-dependent riboswitch.

Journal: FEBS letters 20050509

Title: How an enzyme answers multiple-choice questions.

Journal: Trends in biochemical sciences 20050501

Title: Intermediates and transition states in thiamin diphosphate-dependent decarboxylases. A kinetic and NMR study on wild-type indolepyruvate decarboxylase and variants using indolepyruvate, benzoylformate, and pyruvate as substrates.

Journal: Biochemistry 20050426

Title: Breakdown of 2-hydroxylated straight chain fatty acids via peroxisomal 2-hydroxyphytanoyl-CoA lyase: a revised pathway for the alpha-oxidation of straight chain fatty acids.

Journal: The Journal of biological chemistry 20050318

Title: Biosynthesis of hydroxymethylpyrimidine pyrophosphate in Saccharomyces cerevisiae.

Journal: Current genetics 20050301

Title: Determination of thiamine and its phosphate esters in rat tissues analyzed as thiochromes on a RP-amide C16 column.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050225

Title: Evidence for dramatic acceleration of a C-H bond ionization rate in thiamin diphosphate enzymes by the protein environment.

Journal: Biochemistry 20050222

Title: Elucidating the specificity of binding of sulfonylurea herbicides to acetohydroxyacid synthase.

Journal: Biochemistry 20050222

Title: Outbreak of life-threatening thiamine deficiency in infants in Israel caused by a defective soy-based formula.

Journal: Pediatrics 20050201

Title: Suicide inhibition of acetohydroxyacid synthase by hydroxypyruvate.

Journal: Journal of enzyme inhibition and medicinal chemistry 20050201

Title: Data mining of the transcriptome of Plasmodium falciparum: the pentose phosphate pathway and ancillary processes.

Journal: Malaria journal 20050101

Title: Adult hypophosphatasia and a low level of red blood cell thiamine pyrophosphate.

Journal: Annals of nutrition & metabolism 20050101

Title: Interaction of thiamin diphosphate with phosphorylated and dephosphorylated mammalian pyruvate dehydrogenase complex.

Journal: Biological chemistry 20050101

Title: [Functional activity of blood and liver cells under formaldehyde intoxication via inhalation].

Journal: Biomeditsinskaia khimiia 20050101

Title: Erythrocyte thiamine (Th) esters: a major factor of the alcohol withdrawal syndrome or a candidate marker for alcoholism itself?

Journal: Alcohol and alcoholism (Oxford, Oxfordshire) 20050101

Title: Assay values for thiamine or thiamine phosphate esters in whole blood do not depend on the anticoagulant used.

Journal: Journal of clinical laboratory analysis 20050101

Title: C2-alpha-lactylthiamin diphosphate is an intermediate on the pathway of thiamin diphosphate-dependent pyruvate decarboxylation. Evidence on enzymes and models.

Journal: The Journal of biological chemistry 20041224

Title: [Erythrocyte transketolase].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20041201

Title: Suicidal dephosphorylation of thiamine pyrophosphate coupled with pyruvate dehydrogenase complex.

Journal: The Italian journal of biochemistry 20041201

Title: Effects of deletions at the C-terminus of tobacco acetohydroxyacid synthase on the enzyme activity and cofactor binding.

Journal: The Biochemical journal 20041115

Title: Donor substrate regulation of transketolase.

Journal: European journal of biochemistry 20041101

Title: Biochemistry. How active sites communicate in thiamine enzymes.

Journal: Science (New York, N.Y.) 20041029

Title: A molecular switch and proton wire synchronize the active sites in thiamine enzymes.

Journal: Science (New York, N.Y.) 20041029

Title: The relationship between plasma and red cell concentrations of vitamins thiamine diphosphate, flavin adenine dinucleotide and pyridoxal 5-phosphate following elective knee arthroplasty.

Journal: Clinical nutrition (Edinburgh, Scotland) 20041001

Title: Thiamine pyrophosphate biosynthesis and transport in the nematode Caenorhabditis elegans.

Journal: Genetics 20041001

Title: Optical characteristics of thiamine in model systems and in holoenzyme.

Journal: Biochemistry. Biokhimiia 20040901

Title: The molecular origin of the thiamine diphosphate-induced spectral bands of ThDP-dependent enzymes.

Journal: Proteins 20040801

Title: A new perspective on thiamine catalysis.

Journal: Current opinion in biotechnology 20040801

Title: Electron transfer in acetohydroxy acid synthase as a side reaction of catalysis. Implications for the reactivity and partitioning of the carbanion/enamine form of (alpha-hydroxyethyl)thiamin diphosphate in a 'nonredox' flavoenzyme.

Journal: Biochemistry 20040713

Title: Obese individuals as thiamin storers.

Journal: International journal of obesity and related metabolic disorders : journal of the International Association for the Study of Obesity 20040701

Title: Inhibition of thiamin diphosphate dependent enzymes by 3-deazathiamin diphosphate.

Journal: Organic & biomolecular chemistry 20040621

Title: Kinetic study of the H103A mutant yeast transketolase.

Journal: FEBS letters 20040604

Title: The role of cysteine 160 in thiamine diphosphate binding of the Calvin-Benson-Bassham cycle transketolase of Rhodobacter sphaeroides.

Journal: Archives of biochemistry and biophysics 20040601

Title: Tetrahedral intermediates in thiamin diphosphate-dependent decarboxylations exist as a 1',4'-imino tautomeric form of the coenzyme, unlike the michaelis complex or the free coenzyme.

Journal: Biochemistry 20040601

Title: Structural and biochemical basis for novel mutations in homozygous Israeli maple syrup urine disease patients: a proposed mechanism for the thiamin-responsive phenotype.

Journal: The Journal of biological chemistry 20040423

Title: The reaction of dimethyltin(IV) dichloride with thiamine diphosphate (H2TDP): synthesis and structure of [SnMe2(HTDP)(H2O)]Cl.H2O, and possibility of a hitherto unsuspected role of the metal cofactor in the mechanism of vitamin-B1-dependent enzymes.

Journal: Inorganic chemistry 20040322

Title: Structural determinants of enzyme binding affinity: the E1 component of pyruvate dehydrogenase from Escherichia coli in complex with the inhibitor thiamin thiazolone diphosphate.

Journal: Biochemistry 20040309

Title: Thiamine binding and metabolism in germinating seeds of selected cereals and legumes.

Journal: Plant physiology and biochemistry : PPB 20040301

Title: The crystal structures of Klebsiella pneumoniae acetolactate synthase with enzyme-bound cofactor and with an unusual intermediate.

Journal: The Journal of biological chemistry 20040116

Title: The active site and mechanism of action of recombinant acetohydroxy acid synthase from tobacco.

Journal: FEBS letters 20031204

Title: Effect of thiamine on 3H-MPP+ uptake by Caco-2 cells.

Journal: Pharmacological research 20031201

Title: Three thiamine analogues differently alter thiamine transport and metabolism in nervous tissue: an in vivo kinetic study using rats.

Journal: Metabolic brain disease 20031201

Title: Steady-state kinetics and molecular evolution of Escherichia coli MenD [(1R,6R)-2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase], an anomalous thiamin diphosphate-dependent decarboxylase-carboligase.

Journal: Biochemistry 20031125

Title: An efficient enzymatic synthesis of thiamin pyrophosphate.

Journal: Bioorganic & medicinal chemistry letters 20031117

Title: Dual catalytic apparatus of the thiamin diphosphate coenzyme: acid-base via the 1',4'-iminopyrimidine tautomer along with its electrophilic role.

Journal: Journal of the American Chemical Society 20031022

Title: Genetic control by metabolite-binding riboswitches.

Journal: Chembiochem : a European journal of chemical biology 20031006

Title: Structure and properties of an engineered transketolase from maize.

Journal: Plant physiology 20030801

Title: NMR analysis of covalent intermediates in thiamin diphosphate enzymes.

Journal: Biochemistry 20030708

Title: Structural basis for flip-flop action of thiamin pyrophosphate-dependent enzymes revealed by human pyruvate dehydrogenase.

Journal: The Journal of biological chemistry 20030606

Title: Metabolite-binding RNA domains are present in the genes of eukaryotes.

Journal: RNA (New York, N.Y.) 20030601

Title: Crystal structure of thiamindiphosphate-dependent indolepyruvate decarboxylase from Enterobacter cloacae, an enzyme involved in the biosynthesis of the plant hormone indole-3-acetic acid.

Journal: European journal of biochemistry 20030501

Title: Studies on structure-function relationships of indolepyruvate decarboxylase from Enterobacter cloacae, a key enzyme of the indole acetic acid pathway.

Journal: European journal of biochemistry 20030501

Title: Current mechanistic understanding of thiamin diphosphate-dependent enzymatic reactions.

Journal: Natural product reports 20030401

Title: Pyruvate:NADP+ oxidoreductase is stabilized by its cofactor, thiamin pyrophosphate, in mitochondria of Euglena gracilis.

Journal: Archives of biochemistry and biophysics 20030315

Title: Structural and kinetic analysis of catalysis by a thiamin diphosphate-dependent enzyme, benzoylformate decarboxylase.

Journal: Biochemistry 20030225

Title: The coenzyme thiamine pyrophosphate inhibits the self-splicing of the group I intron.

Journal: The international journal of biochemistry & cell biology 20030201

Title: Effect of intravenous infusions of thiamine on the disposition kinetics of thiamine and its pyrophosphate.

Journal: Journal of clinical pharmacy and therapeutics 20030201

Title: Induced absorption band of holotransketolase and its interpretation.

Journal: Biochemistry. Biokhimiia 20030201

Title: Biochemical characterization of two mutants of human pyruvate dehydrogenase, F205L and T231A of the E1alpha subunit.

Journal: Journal of inherited metabolic disease 20030101

Title: Thiamine pyrophosphate: an essential cofactor in the mammalian metabolism of 3-methyl-branched fatty acids--implications for thiamine deficiencies?

Journal: Advances in experimental medicine and biology 20030101

Title: Thiamin-diphosphate-dependent enzymes: new aspects of asymmetric C-C bond formation.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20021202

Title: A (ribo) switch in the paradigms of genetic regulation.

Journal: Nature structural biology 20021201

Title: Identification and reconstitution of the yeast mitochondrial transporter for thiamine pyrophosphate.

Journal: The EMBO journal 20021101

Title: Molecular biology: RNA gets a grip on translation.

Journal: Nature 20021031

Title: Thiamine derivatives bind messenger RNAs directly to regulate bacterial gene expression.

Journal: Nature 20021031

Title: A novel Y243S mutation in the pyruvate dehydrogenase El alpha gene subunit: correlation with thiamine pyrophosphate interaction.

Journal: Journal of inherited metabolic disease 20020801

Title: Cerebrospinal fluid levels of thiamine in patients with Alzheimer's disease.

Journal: Journal of neural transmission (Vienna, Austria : 1996) 20020701

Title: Spectroscopic evidence for participation of the 1',4'-imino tautomer of thiamin diphosphate in catalysis by yeast pyruvate decarboxylase.

Journal: Bioorganic chemistry 20020601

Title: The origin of the absorption band induced through the interaction between apotransketolase and thiamin diphosphate.

Journal: Biochemical and biophysical research communications 20020531

Title: Structure of the pyruvate dehydrogenase multienzyme complex E1 component from Escherichia coli at 1.85 A resolution.

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Title: [Drug therapy for mitochondrial diseases].

Journal: Nihon rinsho. Japanese journal of clinical medicine 20020401

Title: Growth-phase dependent expression of the mevalonate pathway in a terpenoid antibiotic-producing Streptomyces strain.

Journal: Bioscience, biotechnology, and biochemistry 20020401

Title: Crystal structure of yeast acetohydroxyacid synthase: a target for herbicidal inhibitors.

Journal: Journal of molecular biology 20020322

Title: Practical tethering of vitamin B1 on a silica surface via its phosphate group and evaluation of its activity.

Journal: Chemical communications (Cambridge, England) 20020307

Title: Evaluation of oxidative stress indices during treatment in pregnant women with intrauterine growth retardation.

Journal: Medical science monitor : international medical journal of experimental and clinical research 20020301

Title: Thiamine deficiency in hepatitis C virus and alcohol-related liver diseases.

Journal: Digestive diseases and sciences 20020301

Title: Simultaneous detection of thiamine and its phosphate esters from microalgae by HPLC.

Journal: Biochemical and biophysical research communications 20020222

Title: Characterization of a missense mutation at histidine-44 in a pyruvate dehydrogenase-deficient patient.

Journal: Biochimica et biophysica acta 20020102

Title: Reduced serum concentrations of riboflavine and ascorbic acid, and blood thiamine pyrophosphate and pyridoxal-5-phosphate in geriatric patients with and without pressure sores.

Journal: The journal of nutrition, health & aging 20020101

Title: Mitochondria from cultured cells derived from normal and thiamine-responsive megaloblastic anemia individuals efficiently import thiamine diphosphate.

Journal: BMC biochemistry 20020101

Title: [Relative reactivity of thiamine monophosphate and thiamine diphosphate upon interaction with alkaline phosphatase].

Journal: Ukrains'kyi biokhimichnyi zhurnal (1999 ) 20020101

Title: Regulation of mammalian pyruvate dehydrogenase complex by phosphorylation: complexity of multiple phosphorylation sites and kinases.

Journal: Experimental & molecular medicine 20011231

Title: Enzymology. Coenzymes and radicals.

Journal: Science (New York, N.Y.) 20011221

Title: Crystal structure of the free radical intermediate of pyruvate:ferredoxin oxidoreductase.

Journal: Science (New York, N.Y.) 20011221

Title: Cooperation of divalent ions and thiamin diphosphate in regulation of the function of pig heart pyruvate dehydrogenase complex.

Journal: Journal of nutritional science and vitaminology 20011201

Title: Binding and activation of thiamin diphosphate in acetohydroxyacid synthase.

Journal: Biochemistry 20011002

Title: Functional flexibility of the transketolase molecule.

Journal: Biochemistry. Biokhimiia 20011001

Title: The mechanism of action of bacimethrin, a naturally occurring thiamin antimetabolite.

Journal: Bioorganic & medicinal chemistry letters 20010903

Title: Thiamin auxotrophy in yeast through altered cofactor dependence of the enzyme acetohydroxyacid synthase.

Journal: Microbiology (Reading, England) 20010901

Title: Complexation of Cu(2+) by HETPP and the pentapeptide Asp-Asp-Asn-Lys-Ile: a structural model of the active site of thiamin-dependent enzymes in solution.

Journal: Inorganic chemistry 20010827

Title: Regulation of pyruvate dehydrogenase activity through phosphorylation at multiple sites.

Journal: The Biochemical journal 20010815

Title: Cleaving of ketosubstrates by transketolase and the nature of the products formed.

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Title: Catalytic acid-base groups in yeast pyruvate decarboxylase. 1. Site-directed mutagenesis and steady-state kinetic studies on the enzyme with the D28A, H114F, H115F, and E477Q substitutions.

Journal: Biochemistry 20010626

Title: Examination of donor substrate conversion in yeast transketolase.

Journal: The Journal of biological chemistry 20010511

Title: The use of thiamine and thiamine antagonists to investigate the etiology of early mortality syndrome in lake trout (Salvelinus namaycush).

Journal: Aquatic toxicology (Amsterdam, Netherlands) 20010501

Title: Molecular mechanisms of thiamine utilization.

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Title: Reaction mechanism for mammalian pyruvate dehydrogenase using natural lipoyl domain substrates.

Journal: Archives of biochemistry and biophysics 20010215

Title: Inhibitors of advanced glycation end product-associated protein cross-linking.

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Title: Consequences of a modified putative substrate-activation site on catalysis by yeast pyruvate decarboxylase.

Journal: Biochemistry 20010213

Title: Impact of the reduced folate carrier on the accumulation of active thiamin metabolites in murine leukemia cells.

Journal: The Journal of biological chemistry 20010112

Title: Transketolase abnormality in tolazamide-induced Wernicke's encephalopathy.

Journal: Neurology 19861101

Title: Protection against misonidazole-induced neuropathy in rats: a biochemical assessment.

Journal: Toxicology letters 19830601

Title: The pyruvate-dehydrogenase complex from Azotobacter vinelandii. 2. Regulation of the activity.

Journal: European journal of biochemistry 19751115

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Tags:154-87-0 Molecular Formula|154-87-0 MDL|154-87-0 SMILES|154-87-0 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium chloride |Organic_Building_Blocks