N-[1,3-bis({[(2R,3S,4R,5S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-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: 162114
• Molecular Formular: C46H70F3N7O19S
• Molecular Mass: 1114.1437096
• Monoisotopic Mass: 1113.43992872
• 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]1[C@@H]([C@@H](C(O[C@H]1CO)O)O)O)CO[C@H]1[C@@H]([C@@H](C(O[C@H]1CO)O)O)O
• Canonical SMILES: OC[C@@H]1OC(O)[C@H]([C@H]([C@@H]1OCC(NC(=O)c1ccc(cc1OCCOCCOCCNC(=O)CCCCCNC(=O)CCCCC1SCC2C1NC(=O)N2)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/C46H70F3N7O19S/c47-46(48,49)45(55-56-45)24-9-10-26(41(65)52-25(21-72-39-29(19-57)74-42(66)37(63)35(39)61)22-73-40-30(20-58)75-43(67)38(64)36(40)62)28(18-24)71-17-16-70-15-14-69-13-12-51-33(60)7-2-1-5-11-50-32(59)8-4-3-6-31-34-27(23-76-31)53-44(68)54-34/h9-10,18,25,27,29-31,34-40,42-43,57-58,61-64,66-67H,1-8,11-17,19-23H2,(H,50,59)(H,51,60)(H,52,65)(H2,53,54,68)/t25?,27?,29-,30-,31?,34?,35-,36-,37+,38+,39-,40-,42?,43?/m1/s1
• InChIKey: LAPBPDOPZPGXFE-IUMQPKKASA-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]-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-[1,3-bis({[(2R,3S,4R,5S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-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: PEG-biotincap-ATB-BMPA; N-[2-[2-[2-[(N-Biotinyl-caproylamino)-ethoxy)ethoxyl]-4-[2-(trifluoromethyl)-3H-diazirin-3-yl]benzoyl]-1,3-bis(mannopyranosyl-4-yloxy)-2-propylamine

Database IDs

• CAS Number: 207971-25-3
• PubChem SID: 162256249
• PubChem CID: 71314004

CALCULATED PROPERTIES

• Acid pKa: 11.003256
• H Acceptors: 21
• H Donor: 13
• LogD (pH = 5.5): -2.9015825
• LogD (pH = 7.4): -2.9016893
• Log P: -2.901581
• Molar Refractivity: 255.5997 cm^3
• Polarizability: 100.712 Å^3
• Polar Surface Area: 379.6 Å^2
• Rotatable Bonds: 33
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Ethanol; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 81-83°C

Safety Information

• Storage Condition: Hygroscopic, Store under Inert atmosphere -20°C Freezer

DETAILS

Toronto Research Chemicals - B395740

A 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)