3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-5-[2-(phosphonooxy)ethyl]-1,3-thiazol-3-ium chloride

• ChemBase ID: 129845
• Molecular Formular: C12H18ClN4O4PS
• Molecular Mass: 380.787481
• Monoisotopic Mass: 380.04749039
• SMILES: Cc1c(sc[n+]1Cc1cnc(nc1N)C)CCOP(=O)(O)O.[Cl-]
• Canonical SMILES: Cc1ncc(c(n1)N)C[n+]1csc(c1C)CCOP(=O)(O)O.[Cl-]
• InChI: InChI=1S/C12H17N4O4PS.ClH/c1-8-11(3-4-20-21(17,18)19)22-7-16(8)6-10-5-14-9(2)15-12(10)13;/h5,7H,3-4,6H2,1-2H3,(H3-,13,14,15,17,18,19);1H
• InChIKey: GUGWNSHJDUEHNJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-5-[2-(phosphonooxy)ethyl]-1,3-thiazol-3-ium chloride
• IUPAC Traditional name: thiamin monophosphate chloride
• Synonyms: Thiamine monophosphate; Aneurine monophosphate chloride; Thiamine monophosphate chloride dihydrate

Database IDs

• CAS Number: 532-40-1; 273724-21-3
• EC Number: 208-536-9
• MDL Number: MFCD00063473
• Beilstein Number: 3844977
• PubChem SID: 162224131; 24889085; 24900546
• PubChem CID: 10761
• CHEBI ID: 18338
• Chemspider ID: 10307
• MeSH Name: Thiamine+Monophosphate
• Wikipedia Title: Thiamine_monophosphate

CALCULATED PROPERTIES

• Acid pKa: 1.6589988
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -4.693358
• LogD (pH = 7.4): -5.1419535
• Log P: -5.6963162
• Molar Refractivity: 84.2726 cm^3
• Polarizability: 31.358858 Å^3
• Polar Surface Area: 122.44 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (HPLC)
• Cation Traces: Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: sulfate (SO42-): ≤50 mg/kg
• Empirical Formula (Hill Notation): C12H18ClN4O4PS · 2H2O

DETAILS

Sigma Aldrich - T8637

Biochem/physiol Actions
Thiamine monophosphate (TMP) is used as a substrate of thiamine-phosphate kinase (EC 2.7.4.16) and a precursor of thiamine pyrophosphate (TPP). TPP is a coenzyme involved in the catabolism of sugars and amino acids.

Sigma Aldrich - 88340

Other Notes
Thiamine: Twenty Years of Progress1