3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[(hydrogen phosphonatooxy)(hydroxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium

• ChemBase ID: 1754
• Molecular Formular: C12H18N4O7P2S
• Molecular Mass: 424.306442
• Monoisotopic Mass: 424.0371432
• SMILES: Cc1ncc(C[n+]2csc(CCO[P@@](=O)(O)OP(=O)(O)[O-])c2C)c(N)n1
• Canonical SMILES: Cc1ncc(c(n1)N)C[n+]1csc(c1C)CCO[P@](=O)(OP(=O)(O)[O-])O
• InChI: InChI=1S/C12H18N4O7P2S/c1-8-11(3-4-22-25(20,21)23-24(17,18)19)26-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H4-,13,14,15,17,18,19,20,21)
• InChIKey: AYEKOFBPNLCAJY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[(hydrogen phosphonatooxy)(hydroxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium
• IUPAC Traditional name: β-neurox
• Synonyms: Thiamin Diphosphate

Database IDs

• CAS Number: 154-87-0
• PubChem SID: 46504577; 160965210
• PubChem CID: 5431

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.7583116
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -6.8915963
• LogD (pH = 7.4): -7.19819
• Log P: -5.811122
• Molar Refractivity: 94.0238 cm^3
• Polarizability: 35.948677 Å^3
• Polar Surface Area: 171.8 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.21
• LOG S: -3.11
• Solubility (Water): 3.72e-01 g/l

DETAILS

DrugBank - DB01987

• Drug Groups: experimental
• Description: The coenzyme form of Vitamin B1 present in many animal tissues. It is a required intermediate in the pyruvate dehydrogenase complex and the ketoglutarate dehydrogenase complex. [PubChem]