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

• ChemBase ID: 162112
• Molecular Formular: C25H45N5O6S3
• Molecular Mass: 607.8497
• Monoisotopic Mass: 607.25319719
• SMILES: N1C(=O)N[C@@H]2[C@@H](SC[C@H]12)CCCCC(=O)NCCCCCC(=O)NCCCCCC(=O)NCCSS(=O)(=O)C
• Canonical SMILES: O=C(NCCCCCC(=O)NCCSS(=O)(=O)C)CCCCCNC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2
• InChI: InChI=1S/C25H45N5O6S3/c1-39(35,36)38-17-16-28-23(33)12-5-3-9-14-26-21(31)11-4-2-8-15-27-22(32)13-7-6-10-20-24-19(18-37-20)29-25(34)30-24/h19-20,24H,2-18H2,1H3,(H,26,31)(H,27,32)(H,28,33)(H2,29,30,34)/t19-,20-,24-/m0/s1
• InChIKey: RIKWYYNURUQHAI-SKPFHBQLSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 1038749-81-3
• PubChem SID: 162256247
• PubChem CID: 71314003

CALCULATED PROPERTIES

• Acid pKa: 13.481501
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -0.13248597
• LogD (pH = 7.4): -0.13248238
• Log P: -0.132482
• Molar Refractivity: 155.3437 cm^3
• Polarizability: 61.77638 Å^3
• Polar Surface Area: 162.57 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF; DMSO
• Apperance: Off White Solid
• Melting Point: 133-135°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B395725

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)