ethyl (2S)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate

• ChemBase ID: 168815
• Molecular Formular: C17H23ClO4
• Molecular Mass: 326.81512
• Monoisotopic Mass: 326.1284869
• SMILES: [C@]1(CCCCCCOc2ccc(cc2)Cl)(OC1)C(=O)OCC
• Canonical SMILES: CCOC(=O)[C@@]1(CCCCCCOc2ccc(cc2)Cl)OC1
• InChI: InChI=1S/C17H23ClO4/c1-2-20-16(19)17(13-22-17)11-5-3-4-6-12-21-15-9-7-14(18)8-10-15/h7-10H,2-6,11-13H2,1H3/t17-/m0/s1
• InChIKey: DZLOHEOHWICNIL-KRWDZBQOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2S)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate
• IUPAC Traditional name: ethyl (2S)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate
• Synonyms: (S)-2-[6-(4-Chlorophenoxy)hexyl]oxiranecarboxylic Acid, Ethyl Ester; S-(-)-Etomoxir

Database IDs

• CAS Number: 828934-40-3
• PubChem SID: 162262947
• PubChem CID: 60765

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.380747
• LogD (pH = 7.4): 4.380747
• Log P: 4.380747
• Molar Refractivity: 85.0258 cm^3
• Polarizability: 33.875507 Å^3
• Polar Surface Area: 48.06 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E933510

An inhibitor of carnitine palmitoyltransferase A (CPT1), which is required for the oexidation of long-chain acyl CoA esters. A strong inhibitor of mitochondrial CPT1 and is a candidate as an anti-diabetic drug.

REFERENCES

• Crilley, M.M.L., et al.: Tetrahedron Letters, 30, 7, 885 (1989)