(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-(hydroxymethyl)-3aH,5H,6H,7H,7aH-pyrano[3,2-d][1,3]thiazole-6,7-diol

• ChemBase ID: 178508
• Molecular Formular: C9H16N2O4S
• Molecular Mass: 248.29934
• Monoisotopic Mass: 248.083078
• SMILES: [C@@H]1([C@@H]([C@H]2[C@H](O[C@H]1CO)SC(=N2)NCC)O)O
• Canonical SMILES: CCNC1=N[C@@H]2[C@@H](S1)O[C@H]([C@H]([C@@H]2O)O)CO
• InChI: InChI=1S/C9H16N2O4S/c1-2-10-9-11-5-7(14)6(13)4(3-12)15-8(5)16-9/h4-8,12-14H,2-3H2,1H3,(H,10,11)/t4-,5-,6-,7-,8-/m1/s1
• InChIKey: PPAIMZHKIXDJRN-FMDGEEDCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-(hydroxymethyl)-3aH,5H,6H,7H,7aH-pyrano[3,2-d][1,3]thiazole-6,7-diol
• IUPAC Traditional name: (3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-(hydroxymethyl)-3aH,5H,6H,7H,7aH-pyrano[3,2-d][1,3]thiazole-6,7-diol
• Synonyms: Thiamet G; (3aR,5R,6S,7R,7aR)-2-(Ethylamino)-3a,6,7,7a-tetrahydro-5-(hydroxymethyl)-5H-pyrano[3,2-d]thiazole-6,7-diol; Thiamet GDiscontinued

Database IDs

• CAS Number: 1009816-48-1
• PubChem SID: 164234418
• PubChem CID: 24808478

CALCULATED PROPERTIES

• Acid pKa: 12.792195
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.668683
• LogD (pH = 7.4): -1.2351719
• Log P: -1.01187
• Molar Refractivity: 58.6261 cm^3
• Polarizability: 23.496677 Å^3
• Polar Surface Area: 94.31 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Target: Others

Product Information

• Salt Data: Free Base

DETAILS

Toronto Research Chemicals - T344155

A potent O-GlcNAcase inhibitor that blocks phosphorylation of tau in vivo. The authors anticipate that Thiamet-G will find wide use in probing the functional role of O-GlcNAc in vertebrate brain, and it may also offer a route to blocking pathological hype

REFERENCES

• Chou, T., et al.: J. Biol. Chem., 270, 18961 (1995)
• Cheng, X., et al.; Biochemistry, 39, 11609 (1995)
• Farook, V., et al.: Mol. Genet. Metab., 77, 189 (1995)
• Lefebvre, T., et al.: Biochim. Biophys. Acta, 1619, 167 (1995)
• Cho, J., et al.: J. Neurochem.,