(3S)-3-hexyl-4-[(2R)-2-hydroxytridecyl]oxetan-2-one

• ChemBase ID: 169978
• Molecular Formular: C22H42O3
• Molecular Mass: 354.56708
• Monoisotopic Mass: 354.3133952
• SMILES: C(CCCCCCCCC[C@@H](O)CC1OC(=O)[C@H]1CCCCCC)C
• Canonical SMILES: CCCCCCCCCCC[C@H](CC1OC(=O)[C@H]1CCCCCC)O
• InChI: InChI=1S/C22H42O3/c1-3-5-7-9-10-11-12-13-14-16-19(23)18-21-20(22(24)25-21)17-15-8-6-4-2/h19-21,23H,3-18H2,1-2H3/t19-,20+,21?/m1/s1
• InChIKey: RSOUWOFYULUWNE-PDYHCXRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-hexyl-4-[(2R)-2-hydroxytridecyl]oxetan-2-one
• IUPAC Traditional name: (3S)-3-hexyl-4-[(2R)-2-hydroxytridecyl]oxetan-2-one
• Synonyms: [3S-[3α,4β(S*)]]-3-Hexyl-4-(2-hydroxytridecyl)-2-oxetanone; (3S,4S)-3-Hexyl-4-[(2R)-2-hydroxytridecyl]-2-oxetanone

Database IDs

• CAS Number: 104872-06-2
• PubChem SID: 162264110
• PubChem CID: 58361990

CALCULATED PROPERTIES

• Acid pKa: 15.175213
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 6.99656
• LogD (pH = 7.4): 6.99656
• Log P: 6.99656
• Molar Refractivity: 104.3123 cm^3
• Polarizability: 41.90784 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H296530

(3S,4S)-3-Hexyl-4-[(2R)-2-hydroxytridecyl]-2-oxetanone is an analog of Tetrahydrolipstatin, an inhibitor of the hydrolysis of endocannabinoid 2-arachidonoylglycerol (2-AG), also an intermediate in the preparation of Orlistat (O686500).

REFERENCES

• Di Marzo, V., et al.: Nat. Rev. Drug Discovery, 7, 438 (1995)
• Ortar, G., et al.: J. Med. Chem., 51, 6970 (1995)
• Mechoulam, R., et al.: Biochem. Pharmacol., 50, 83 (1995)
• Bisogno, T., et al.: J. Cell Biol., 163, 463 (1995)