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

• ChemBase ID: 154094
• Molecular Formular: C13H23N3O4S3
• Molecular Mass: 381.53442
• Monoisotopic Mass: 381.08506923
• SMILES: CS(=O)(=O)SCCNC(=O)CCCC[C@H]1[C@@H]2[C@H](CS1)NC(=O)N2
• Canonical SMILES: O=C(NCCSS(=O)(=O)C)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2
• InChI: InChI=1S/C13H23N3O4S3/c1-23(19,20)22-7-6-14-11(17)5-3-2-4-10-12-9(8-21-10)15-13(18)16-12/h9-10,12H,2-8H2,1H3,(H,14,17)(H2,15,16,18)/t9-,10-,12-/m0/s1
• InChIKey: CQPWMXNDGWWWHG-NHCYSSNCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]-N-[2-(methanesulfonylsulfanyl)ethyl]pentanamide
• IUPAC Traditional name: 5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]-N-[2-(methanesulfonylsulfanyl)ethyl]pentanamide
• Synonyms: Methanesulfonothioic Acid S-[2-[[5-[(3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl]-1-oxopentyl]amino]ethyl] Ester; MTSEA-BIOTIN; N-Biotinylaminoethyl Methanethiosulfonate; 2-((Biotinoyl)amino)ethyl methanethiosulfonate; 2-[(Biotinoyl)-amino]-ethyl-methanthiosulfonat; N-Biotinylaminoethyl methanethiosulfonate; MTSEA Biotin

Database IDs

• CAS Number: 162758-04-5
• MDL Number: MFCD01320376
• PubChem SID: 162248233
• PubChem CID: 29973978

CALCULATED PROPERTIES

• Acid pKa: 13.486689
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.7515388
• LogD (pH = 7.4): -0.7515384
• Log P: -0.7515381
• Molar Refractivity: 92.4239 cm^3
• Polarizability: 37.264103 Å^3
• Polar Surface Area: 104.37 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; DMSO: soluble
• Apperance: White Solid
• Melting Point: 95-103°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C13H23N3O4S3

DETAILS

Sigma Aldrich - 44521

Biochem/physiol Actions
Thiol-reactive reagent for labeling proteins at cysteine residues to study structure and function.

Toronto Research Chemicals - B394750

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. MTSEA-biotin has recently been used to probe the topology of the seroto

REFERENCES

• J. Biol. Chem., 273(20)
• 12675 (20)
• Adams, C.M., et al.: J. Biol. Chem., 273 (20)
• 30204 (20)
• Boileau, A. J., et al.: J. Neurosci., 19, 12, 4847 (20)
• Wagner, D.A.and Czajkowski, C.: J. Neurosci., 21, 67 (20)
• Traebert, M.: J. Membr. Biol., 180