N-(1-{[(6R)-4,4-dimethyl-3,5,10,11-tetraoxatricyclo[6.2.1.02,6]undecan-7-yl]oxy}-3-{[(6S,7R)-4,4-dimethyl-3,5,10,11-tetraoxatricyclo[6.2.1.02,6]undecan-7-yl]oxy}propan-2-yl)-2-[2-(2-{2-[6-(5-{2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl}pentanamido)hexanamido]ethoxy}ethoxy)ethoxy]-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzamide

• ChemBase ID: 162093
• Molecular Formular: C52H74F3N7O17S
• Molecular Mass: 1158.2408696
• Monoisotopic Mass: 1157.4813996
• SMILES: c1cc(c(cc1C1(N=N1)C(F)(F)F)OCCOCCOCCNC(=O)CCCCCNC(=O)CCCCC1C2C(CS1)NC(=O)N2)C(=O)NC(CO[C@@H]1C2OC(OC2)C2[C@@H]1OC(O2)(C)C)COC1C2OC(OC2)C2[C@H]1OC(O2)(C)C
• Canonical SMILES: O=C(CCCCCNC(=O)CCCCC1SCC2C1NC(=O)N2)NCCOCCOCCOc1cc(ccc1C(=O)NC(COC1C2COC(O2)C2[C@H]1OC(O2)(C)C)CO[C@@H]1C2COC(O2)C2[C@@H]1OC(O2)(C)C)C1(N=N1)C(F)(F)F
• InChI: InChI=1S/C52H74F3N7O17S/c1-49(2)76-41-39(33-25-72-46(74-33)43(41)78-49)70-23-29(24-71-40-34-26-73-47(75-34)44-42(40)77-50(3,4)79-44)58-45(65)30-14-13-28(51(61-62-51)52(53,54)55)22-32(30)69-21-20-68-19-18-67-17-16-57-37(64)11-6-5-9-15-56-36(63)12-8-7-10-35-38-31(27-80-35)59-48(66)60-38/h13-14,22,29,31,33-35,38-44,46-47H,5-12,15-21,23-27H2,1-4H3,(H,56,63)(H,57,64)(H,58,65)(H2,59,60,66)/t29?,31?,33?,34?,35?,38?,39-,40?,41+,42-,43?,44?,46?,47?/m1/s1
• InChIKey: QXDYFOMUYRCYJR-UWWDYXODSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(1-{[(6R)-4,4-dimethyl-3,5,10,11-tetraoxatricyclo[6.2.1.0^2,^6]undecan-7-yl]oxy}-3-{[(6S,7R)-4,4-dimethyl-3,5,10,11-tetraoxatricyclo[6.2.1.0^2,^6]undecan-7-yl]oxy}propan-2-yl)-2-[2-(2-{2-[6-(5-{2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl}pentanamido)hexanamido]ethoxy}ethoxy)ethoxy]-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzamide
• IUPAC Traditional name: N-(1-{[(6R)-4,4-dimethyl-3,5,10,11-tetraoxatricyclo[6.2.1.0^2,^6]undecan-7-yl]oxy}-3-{[(6S,7R)-4,4-dimethyl-3,5,10,11-tetraoxatricyclo[6.2.1.0^2,^6]undecan-7-yl]oxy}propan-2-yl)-2-[2-(2-{2-[6-(5-{2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl}pentanamido)hexanamido]ethoxy}ethoxy)ethoxy]-4-[3-(trifluoromethyl)diazirin-3-yl]benzamide
• Synonyms: 2-[2-[2-[2-[6-(Biotinylaminohexanoyl]aminoethoxy]ethoxy]ethoxy]-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzoic Acid 1,3-Bis[1,6-anhydro-2,3-O-isopropylidene-β-D-mannopyranos-4-yloxy)-2-propylamine Amide

Database IDs

• PubChem SID: 162256228
• PubChem CID: 71313992

CALCULATED PROPERTIES

• Acid pKa: 13.377385
• H Acceptors: 19
• H Donor: 5
• LogD (pH = 5.5): 2.8266728
• LogD (pH = 7.4): 2.826675
• Log P: 2.8266752
• Molar Refractivity: 272.9935 cm^3
• Polarizability: 107.80814 Å^3
• Polar Surface Area: 273.14 Å^2
• Rotatable Bonds: 31
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 57-59°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B394860

A protected, cross-linking, biotin-labelled compound 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)
• Koumanov F., et al: Biochem. J. 330, 1209 (1990)
• Hatanaka, Y. et al: Bioorg. Med. Chem., 2, 1367 (1994)