1-{4-[(1R,2S,3R)-1,2,3,4-tetrahydroxybutyl]-1H-imidazol-2-yl}ethan-1-one

• ChemBase ID: 154765
• Molecular Formular: C9H14N2O5
• Molecular Mass: 230.21786
• Monoisotopic Mass: 230.09027156
• SMILES: CC(=O)c1[nH]cc(n1)[C@H]([C@@H]([C@@H](CO)O)O)O
• Canonical SMILES: CC(=O)c1nc(c[nH]1)[C@H]([C@@H]([C@@H](CO)O)O)O
• InChI: InChI=1S/C9H14N2O5/c1-4(13)9-10-2-5(11-9)7(15)8(16)6(14)3-12/h2,6-8,12,14-16H,3H2,1H3,(H,10,11)/t6-,7-,8-/m1/s1
• InChIKey: CQSIXFHVGKMLGQ-BWZBUEFSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{4-[(1R,2S,3R)-1,2,3,4-tetrahydroxybutyl]-1H-imidazol-2-yl}ethan-1-one
• IUPAC Traditional name: 1-{4-[(1R,2S,3R)-1,2,3,4-tetrahydroxybutyl]-1H-imidazol-2-yl}ethanone
• Synonyms: 2-Acetyl-4-tetrahydroxybutyl Imidazole; 1-[5-[(1R,2S,3R)-1,2,3,4-tetrahydroxybutyl]-1H-imidazol-2-yl]-ethanone; 2-ATHBI; THI

Database IDs

• CAS Number: 94944-70-4
• MDL Number: MFCD08752516
• PubChem SID: 162248903
• PubChem CID: 108037

CALCULATED PROPERTIES

• Acid pKa: 9.354813
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -2.6370192
• LogD (pH = 7.4): -2.639367
• Log P: -2.6347253
• Molar Refractivity: 53.1491 cm^3
• Polarizability: 20.92566 Å^3
• Polar Surface Area: 126.67 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >5 mg/mL
• Apperance: off-white to light brown powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: 2-8°C

Product Information

• Empirical Formula (Hill Notation): C9H14N2O5

DETAILS

Sigma Aldrich - T6330

Biochem/physiol Actions
THI is an inhibitor of sphingosine-1-phosphate lyase and acts as an immunosuppressant. Sphingosine-1-phosphate (S1P) lyase catalyzes the irreversible decomposition of S1P to hexadecanaldehyde and phosphoethanolamine. Reducing S1P lyase activity results in therapeutic levels of immunosuppression without the non-lymphoid lesions that result from synthetic S1P receptor agonists.