5-(2-hydroxyethyl)-4-methyl-3-[(2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl)methyl]-1,3-thiazol-3-ium chloride hydrochloride

• ChemBase ID: 133599
• Molecular Formular: C12H17Cl2N3O2S
• Molecular Mass: 338.25328
• Monoisotopic Mass: 337.04185316
• SMILES: Cc1[nH]c(=O)c(cn1)C[n+]1csc(c1C)CCO.Cl.[Cl-]
• Canonical SMILES: OCCc1sc[n+](c1C)Cc1cnc([nH]c1=O)C.Cl.[Cl-]
• InChI: InChI=1S/C12H15N3O2S.2ClH/c1-8-11(3-4-16)18-7-15(8)6-10-5-13-9(2)14-12(10)17;;/h5,7,16H,3-4,6H2,1-2H3;2*1H
• InChIKey: HGYQKVVWNZFPJS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(2-hydroxyethyl)-4-methyl-3-[(2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl)methyl]-1,3-thiazol-3-ium chloride hydrochloride
• IUPAC Traditional name: 5-(2-hydroxyethyl)-4-methyl-3-[(2-methyl-4-oxo-3H-pyrimidin-5-yl)methyl]-1,3-thiazol-3-ium chloride hydrochloride
• Synonyms: 5-(2-Hydroxyethyl)-3-(4-hydroxy-2-methyl-5-pyrimidinylmethyl)-4-methylthiazolium chloride; Oxythiamine chloride hydrochloride

Database IDs

• CAS Number: 614-05-1
• MDL Number: MFCD00050656
• PubChem SID: 162227876; 24897990
• PubChem CID: 101796

CALCULATED PROPERTIES

• Acid pKa: 11.412238
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -3.9551604
• LogD (pH = 7.4): -3.955196
• Log P: -3.9551585
• Molar Refractivity: 69.7047 cm^3
• Polarizability: 26.419945 Å^3
• Polar Surface Area: 65.57 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: XJ7034100
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)

DETAILS

Sigma Aldrich - O4000

Biochem/physiol Actions
Oxythiamine inhibits Transketolase, the enzyme that controls the nonoxidative branch of the pentose phosphate pathway.
Oxythiamine (OT) is a thiamine antagonist that may be used as a transketolase inhibitor and to study anti-metastatic mechamisms, especially those involving metalloproteinases (MMP).