6-[6-(6-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}hexanamido)hexanamido]-N-[2-(methanesulfonylsulfanyl)ethyl]hexanamide

• ChemBase ID: 162110
• Molecular Formular: C31H56N6O7S3
• Molecular Mass: 721.00734
• Monoisotopic Mass: 720.33726116
• SMILES: N1C(=O)N[C@@H]2[C@@H](SC[C@H]12)CCCCC(=O)NCCCCCC(=O)NCCCCCC(=O)NCCCCCC(=O)NCCSS(=O)(=O)C
• Canonical SMILES: O=C(NCCCCCC(=O)NCCCCCC(=O)NCCSS(=O)(=O)C)CCCCCNC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2
• InChI: InChI=1S/C31H56N6O7S3/c1-47(43,44)46-22-21-35-29(41)16-7-4-12-19-33-27(39)14-5-2-10-18-32-26(38)15-6-3-11-20-34-28(40)17-9-8-13-25-30-24(23-45-25)36-31(42)37-30/h24-25,30H,2-23H2,1H3,(H,32,38)(H,33,39)(H,34,40)(H,35,41)(H2,36,37,42)/t24-,25-,30-/m0/s1
• InChIKey: OTHVURBITOMQHQ-QRQMUESOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-[6-(6-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}hexanamido)hexanamido]-N-[2-(methanesulfonylsulfanyl)ethyl]hexanamide
• IUPAC Traditional name: 6-[6-(6-{5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanamido}hexanamido)hexanamido]-N-[2-(methanesulfonylsulfanyl)ethyl]hexanamide
• Synonyms: MTSEA-BIOTINCAPCAPCAP; N-Biotinylcaproylaminocaproylaminocaproylaminoethyl Methanethiosulfonate

Database IDs

• PubChem SID: 162256245
• PubChem CID: 71314001

CALCULATED PROPERTIES

• Acid pKa: 13.483537
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): 0.17704046
• LogD (pH = 7.4): 0.17704563
• Log P: 0.17704602
• Molar Refractivity: 186.8036 cm^3
• Polarizability: 74.03681 Å^3
• Polar Surface Area: 191.67 Å^2
• Rotatable Bonds: 27
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF; DMSO
• Apperance: White Solid
• Melting Point: 171-173°C

Safety Information

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

DETAILS

Toronto Research Chemicals - B395715

Reacts specifically and rapidly with thiols to form mixed disulfides. Used to probe the structures of the ACh receptor channel of the GABA receptor channel and of lactose permease.

REFERENCES

• Wagner, D.A.and Czajkowski, C.: J. Neurosci., 21, 67 (2001)
• Traebert, M.: J. Membr. Biol., 180, 83 (2001)