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

• ChemBase ID: 162067
• Molecular Formular: C11H16N2O5S
• Molecular Mass: 288.32014
• Monoisotopic Mass: 288.07799262
• SMILES: N1C(=O)N[C@@H]2[C@@H](SC[C@H]12)CCCC(C(=O)O)C(=O)O
• Canonical SMILES: O=C1N[C@@H]2[C@H](N1)[C@@H](SC2)CCCC(C(=O)O)C(=O)O
• InChI: InChI=1S/C11H16N2O5S/c14-9(15)5(10(16)17)2-1-3-7-8-6(4-19-7)12-11(18)13-8/h5-8H,1-4H2,(H,14,15)(H,16,17)(H2,12,13,18)/t6-,7-,8-/m0/s1
• InChIKey: XWJBVGZSIAZDKJ-FXQIFTODSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{3-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]propyl}propanedioic acid
• IUPAC Traditional name: 2-{3-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]propyl}propanedioic acid
• Synonyms: 2-[3-[(3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl]propyl]propanedioic Acid; Biotin Diacid

Database IDs

• CAS Number: 57671-79-1
• PubChem SID: 162256202
• PubChem CID: 22865898

CALCULATED PROPERTIES

• Acid pKa: 2.4978225
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -2.8788998
• LogD (pH = 7.4): -4.4265785
• Log P: 0.054102525
• Molar Refractivity: 66.3426 cm^3
• Polarizability: 26.196955 Å^3
• Polar Surface Area: 115.73 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B390600

Biotin (B389040) impurity.

REFERENCES

• Trotter, J., et al.: Biochemistry, 5, 713 (1966)
• Suurkuusk, J., et al.: Eur. J.Biochem., 28, 438 (1966)