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

• ChemBase ID: 162118
• Molecular Formular: C16H30N4O2S
• Molecular Mass: 342.5
• Monoisotopic Mass: 342.20894722
• SMILES: N1C(=O)N[C@@H]2[C@@H](SC[C@H]12)CCCCC(=O)NCCCCCCN
• Canonical SMILES: NCCCCCCNC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2
• InChI: InChI=1S/C16H30N4O2S/c17-9-5-1-2-6-10-18-14(21)8-4-3-7-13-15-12(11-23-13)19-16(22)20-15/h12-13,15H,1-11,17H2,(H,18,21)(H2,19,20,22)/t12-,13-,15-/m0/s1
• InChIKey: QWVNTBHBRBLRRJ-YDHLFZDLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]-N-(6-aminohexyl)pentanamide
• IUPAC Traditional name: 5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]-N-(6-aminohexyl)pentanamide
• Synonyms: [3aS-(3aα,4β,6aα)]-N-(6-Aminohexyl)hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanamide; (3aS,4S,6aR)-N-(6-Aminohexyl)hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanamide; N-Biotinyl-1,6-hexanediamine

Database IDs

• CAS Number: 65953-56-2
• PubChem SID: 162256253
• PubChem CID: 11121441

CALCULATED PROPERTIES

• Acid pKa: 13.493679
• H Acceptors: 3
• H Donor: 4
• LogD (pH = 5.5): -2.6183562
• LogD (pH = 7.4): -2.1985602
• Log P: 0.40563303
• Molar Refractivity: 93.4316 cm^3
• Polarizability: 36.899067 Å^3
• Polar Surface Area: 96.25 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 184-186°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B395885

Intermediate in the preparation of serum biotinidase resistant Biotin derivatives used to make pretargeted diagnosis of tumors.

REFERENCES

• Sabatino, G., et al.: J. Med. Chem., 46, 3170 (2003)
• Lu, L., et al.: Bioorg. Med. Chem., 17, 7548 (2003)