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

• ChemBase ID: 92804
• Molecular Formular: C19H34N4O5S3
• Molecular Mass: 494.69206
• Monoisotopic Mass: 494.16913321
• SMILES: N1C(=O)N[C@@H]2[C@H]1[C@@H](SC2)CCCCC(=O)NCCCCCC(=O)NCCSS(=O)(=O)C
• Canonical SMILES: O=C(NCCCCCC(=O)NCCSS(=O)(=O)C)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2
• InChI: InChI=1S/C19H34N4O5S3/c1-31(27,28)30-12-11-21-17(25)8-3-2-6-10-20-16(24)9-5-4-7-15-18-14(13-29-15)22-19(26)23-18/h14-15,18H,2-13H2,1H3,(H,20,24)(H,21,25)(H2,22,23,26)/t14-,15-,18-/m0/s1
• InChIKey: PXMZUZLKVZKKHK-MPGHIAIKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}-N-[2-(methanesulfonylsulfanyl)ethyl]hexanamide
• IUPAC Traditional name: 6-{5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanamido}-N-[2-(methanesulfonylsulfanyl)ethyl]hexanamide
• Synonyms: Methanesulfonothioic Acid, S-[2-[[6-[[5-[(3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl]-1-oxopentyl]amino]-1-oxohexyl]amino]ethyl] Ester; N-Biotinylcaproylaminoethyl Methanethiosulfonate; 2-((6-((Biotinoyl)amino)hexanoyl)amino)ethyl methanethiosulfonate; MTSEA Biotin-X; MTSEA-BIOTINCAP; N-Biotinylcaproylaminoethyl methylthiosulphonate; 2-((6-((Biotinoyl)-amino)-hexanoyl)-amino)-ethyl-methanthiosulfonat

Database IDs

• CAS Number: 353754-95-7
• MDL Number: MFCD03453615
• PubChem SID: 162079502
• PubChem CID: 71299596

CALCULATED PROPERTIES

• Acid pKa: 13.483324
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -0.4420124
• LogD (pH = 7.4): -0.4420104
• Log P: -0.44201005
• Molar Refractivity: 123.8838 cm^3
• Polarizability: 49.51814 Å^3
• Polar Surface Area: 133.47 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; DMSO: soluble
• Apperance: Off White Solid
• Melting Point: 122-124°C; 133-135°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Irritant/Moisture Sensitive/Light Sensitive/Store at -20°C/Store under Argon
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: -20°C

Product Information

• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C19H34N4O5S3

DETAILS

Apollo Scientific Ltd - OR9575T

Reacts specifically & rapidly with thiols to form mixed disulfides. Used to probe the structures of the ACh receptor channel of the GABAA receptor channel.

Sigma Aldrich - 91257

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

Toronto Research Chemicals - B395750

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)