5-[(3aS,4S,6aR)-1-benzyl-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoic acid

• ChemBase ID: 161437
• Molecular Formular: C17H22N2O3S
• Molecular Mass: 334.43318
• Monoisotopic Mass: 334.13511357
• SMILES: N1C(=O)N([C@H]2CS[C@@H](CCCCC(=O)O)[C@@H]12)Cc1ccccc1
• Canonical SMILES: OC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2Cc1ccccc1
• InChI: InChI=1S/C17H22N2O3S/c20-15(21)9-5-4-8-14-16-13(11-23-14)19(17(22)18-16)10-12-6-2-1-3-7-12/h1-3,6-7,13-14,16H,4-5,8-11H2,(H,18,22)(H,20,21)/t13-,14-,16-/m0/s1
• InChIKey: MFFWFILLMGRYPI-DZKIICNBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(3aS,4S,6aR)-1-benzyl-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoic acid
• IUPAC Traditional name: 5-[(3aS,4S,6aR)-1-benzyl-2-oxo-tetrahydro-3H-thieno[3,4-d]imidazolidin-4-yl]pentanoic acid
• Synonyms: (3aS,4S,6aR)-Hexahydro-2-oxo-1-(phenylmethyl)-1H-thieno[3,4-d]imidazole-4-pentanoic Acid; [3aS-(3aα,4β,6aα)]-Hexahydro-2-oxo-1-(phenylmethyl)-1H-thieno[3,4-d]imidazole-4-pentanoic Acid; 1-Benzyltetrahydro-2-oxo-thieno[3,4-d]imidazoline-4-valeric Acid; 1'N-Benzyl Biotin

Database IDs

• CAS Number: 76335-62-1
• PubChem SID: 162255572
• PubChem CID: 10314840

CALCULATED PROPERTIES

• Acid pKa: 4.2692685
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.0142105
• LogD (pH = 7.4): -0.71757966
• Log P: 2.2675729
• Molar Refractivity: 89.5602 cm^3
• Polarizability: 35.062767 Å^3
• Polar Surface Area: 69.64 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B233025

A biotin derivative used in the novel enantioselective syntheses of (+)-Biotin.

REFERENCES

• Robinson, A.E.., et al.: J. Pharma. Pharmacol., 16, 342 (1964)