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

• ChemBase ID: 162068
• Molecular Formular: C18H28N4O4S2
• Molecular Mass: 428.56932
• Monoisotopic Mass: 428.1551974
• SMILES: N1C(=O)N[C@@H]2[C@@H](SC[C@H]12)CCCC(CCC[C@@H]1SC[C@@H]2NC(=O)N[C@H]12)C(=O)O
• Canonical SMILES: OC(=O)C(CCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2)CCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2
• InChI: InChI=1S/C18H28N4O4S2/c23-16(24)9(3-1-5-12-14-10(7-27-12)19-17(25)21-14)4-2-6-13-15-11(8-28-13)20-18(26)22-15/h9-15H,1-8H2,(H,23,24)(H2,19,21,25)(H2,20,22,26)/t10-,11-,12-,13-,14-,15-/m0/s1
• InChIKey: ONCAVQWGAJQDNB-LZXPERKUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]-2-{3-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]propyl}pentanoic acid
• IUPAC Traditional name: 5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]-2-{3-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]propyl}pentanoic acid
• Synonyms: D-Biotin Dimer Acid

Database IDs

• CAS Number: 1163708-46-0
• PubChem SID: 162256203
• PubChem CID: 71313974

CALCULATED PROPERTIES

• Acid pKa: 4.345854
• H Acceptors: 4
• H Donor: 5
• LogD (pH = 5.5): -0.47711042
• LogD (pH = 7.4): -2.2244976
• Log P: 0.7046434
• Molar Refractivity: 107.4057 cm^3
• Polarizability: 42.416615 Å^3
• Polar Surface Area: 119.56 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B390650

D-Biotin impurity. Used in the synthesis of D-Biotin.

REFERENCES

• Hanka, L.J., Antimicrob. Agents Chemother., 1, 135 (1972)
• Corey, E.J., et al.: Tetrahedon Lett., 29, 57 (1972)