6-(5-methyl-2-oxoimidazolidin-4-yl)hexanoic acid

• ChemBase ID: 108061
• Molecular Formular: C10H18N2O3
• Molecular Mass: 214.26152
• Monoisotopic Mass: 214.13174245
• SMILES: CC1NC(=O)NC1CCCCCC(=O)O
• Canonical SMILES: OC(=O)CCCCCC1NC(=O)NC1C
• InChI: InChI=1S/C10H18N2O3/c1-7-8(12-10(15)11-7)5-3-2-4-6-9(13)14/h7-8H,2-6H2,1H3,(H,13,14)(H2,11,12,15)
• InChIKey: AUTOLBMXDDTRRT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-(5-methyl-2-oxoimidazolidin-4-yl)hexanoic acid
• IUPAC Traditional name: desthiobiotin; dethiobiotin
• Synonyms: DL-DESTHIOBIOTIN; (4R,5S)-rel-5-Methyl-2-oxo-4-imidazolidinehexanoic Acid; cis-5-Methyl-2-oxo-4-imidazolidinehexanoic Acid; cis-(±)-5-Methyl-2-oxo-4-imidazolidinehexanoic Acid; (±)-Desthiobiotin; (±)-Dethiobiotin; NSC 203773; dl-Desthiobiotin; dl-Dethiobiotin; rac-Desthio Biotin

Database IDs

• CAS Number: 636-20-4
• PubChem SID: 162094006
• PubChem CID: 643

CALCULATED PROPERTIES

• Acid pKa: 4.6346555
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.19421802
• LogD (pH = 7.4): -1.9714122
• Log P: 0.72569865
• Molar Refractivity: 54.398 cm^3
• Polarizability: 21.348757 Å^3
• Polar Surface Area: 78.43 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

MP Biomedicals - 05205919

MP Biomedicals Rare Chemical collection

Toronto Research Chemicals - D297490

rac-Desthiobiotin is useful as an intermediate in the synthesis of Biotin. The conversion of Dethiobiotin into Biotin was studied in Escherichia coli by starting from specifically deuterated precursors.

REFERENCES

• Tsuboi, T., et al.: Chem. Pharmaceut. Bull., 24, 1123 (1976)
• Li, H.-C., et al.: J. Biol. Chem., 243, 4391 (1976)