5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]-N-{2-[(2R)-2-amino-3-sulfanylpropanamido]ethyl}pentanamide; trifluoroacetic acid

• ChemBase ID: 162117
• Molecular Formular: C17H28F3N5O5S2
• Molecular Mass: 503.5599296
• Monoisotopic Mass: 503.14839568
• SMILES: N1C(=O)N[C@@H]2[C@@H](SC[C@H]12)CCCCC(=O)NCCNC(=O)[C@H](CS)N.C(F)(F)(F)C(=O)O
• Canonical SMILES: OC(=O)C(F)(F)F.SC[C@@H](C(=O)NCCNC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2)N
• InChI: InChI=1S/C15H27N5O3S2.C2HF3O2/c16-9(7-24)14(22)18-6-5-17-12(21)4-2-1-3-11-13-10(8-25-11)19-15(23)20-13;3-2(4,5)1(6)7/h9-11,13,24H,1-8,16H2,(H,17,21)(H,18,22)(H2,19,20,23);(H,6,7)/t9-,10-,11-,13-;/m0./s1
• InChIKey: JUVXYXRFWCRTHH-PQMNFAHESA-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-[(2R)-2-amino-3-sulfanylpropanamido]ethyl}pentanamide; trifluoroacetic acid
• IUPAC Traditional name: 5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]-N-{2-[(2R)-2-amino-3-sulfanylpropanamido]ethyl}pentanamide; trifluoroacetic acid
• Synonyms: (3aS,4S,6aR)-N-[2-[[(2R)-2-Amino-3-mercapto-1-oxopropyl]amino]ethyl]hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanamide Trifluoroacetic Acid Salt; N-Biotinyl-N'-cysteinyl Ethylenediamine Trifluoroacetic Acid Salt

Database IDs

• PubChem SID: 162256252
• PubChem CID: 71314007

CALCULATED PROPERTIES

• Acid pKa: 9.981175
• H Acceptors: 4
• H Donor: 6
• LogD (pH = 5.5): -3.9944606
• LogD (pH = 7.4): -2.3043547
• Log P: -1.6322626
• Molar Refractivity: 99.7433 cm^3
• Polarizability: 39.38619 Å^3
• Polar Surface Area: 125.35 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 51-53°C

Safety Information

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

DETAILS

Toronto Research Chemicals - B395826

A useful reagent for intein-mediated biotinylation of proteins and subsequent use in a protein microarray.

REFERENCES

• Muller, W., et al.: Science, 262, 1706 (1993)
• Pasqualini, R., et al.: Nat. Biotechnol., 15, 542 (1993)
• Curnis, F., et al.: Cancer Res., 62, 867 (1993)
• Langereis, S., et al.: Org. Biomol. Chem., 2, 1271 (1993)