N-[1,3-bis({[(2R,3S,4R,5S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy})propan-2-yl]-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzamide

• ChemBase ID: 161086
• Molecular Formular: C24H32F3N3O13
• Molecular Mass: 627.5183896
• Monoisotopic Mass: 627.18872276
• SMILES: c1cc(ccc1C(=O)NC(CO[C@H]1[C@@H]([C@@H](C(O[C@H]1CO)O)O)O)CO[C@@H]1[C@H](OC([C@H]([C@@H]1O)O)O)CO)C1(N=N1)C(F)(F)F
• Canonical SMILES: OC[C@@H]1OC(O)[C@H]([C@H]([C@@H]1OCC(NC(=O)c1ccc(cc1)C1(N=N1)C(F)(F)F)CO[C@@H]1[C@@H](CO)OC([C@H]([C@@H]1O)O)O)O)O
• InChI: InChI=1S/C24H32F3N3O13/c25-24(26,27)23(29-30-23)10-3-1-9(2-4-10)20(37)28-11(7-40-18-12(5-31)42-21(38)16(35)14(18)33)8-41-19-13(6-32)43-22(39)17(36)15(19)34/h1-4,11-19,21-22,31-36,38-39H,5-8H2,(H,28,37)/t11?,12-,13-,14-,15-,16+,17+,18-,19-,21?,22?/m1/s1
• InChIKey: NPJHSWNPVIJJGQ-YPYGJDMNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[1,3-bis({[(2R,3S,4R,5S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy})propan-2-yl]-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzamide
• IUPAC Traditional name: N-[1,3-bis({[(2R,3S,4R,5S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy})propan-2-yl]-4-[3-(trifluoromethyl)diazirin-3-yl]benzamide
• Synonyms: 4,4'-O-[2-[[4-[3-(Trifluoromethyl)-3H-diazirin-3-yl]benzoyl]amino]-1,3-propanediyl]bis-D-mannose; ATB-BMPA; 2-N-[4-(1-Azitrifluoroethyl)benzoyl]-1,3-bis-(D-mannos -4-yloxy)-2-propylamine

Database IDs

• CAS Number: 129461-18-3
• PubChem SID: 162255221
• PubChem CID: 71313608

CALCULATED PROPERTIES

• Acid pKa: 11.004429
• H Acceptors: 15
• H Donor: 9
• LogD (pH = 5.5): -2.5241203
• LogD (pH = 7.4): -2.524227
• Log P: -2.524119
• Molar Refractivity: 130.7888 cm^3
• Polarizability: 51.819553 Å^3
• Polar Surface Area: 252.58 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Soluble in Physiological Buffers; Water
• Apperance: Off-White Solid
• Melting Point: 105-107°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A927500

Used as an exofacial probe for the human erythrocyte glucose transport system. The compound is impermeable and photolabeling can be confined to the discrete plasma membrane pool of glucose transporters.

REFERENCES

• Holman, G.D., et al.: J. Biol. Chem., 265, 30, 18172 (1990)
• Holman, G.D., et al.: Biochem. J., 269, 615 (1990)