(2S)-1-[(2S,3R)-3-hexyloxetan-2-yl]tridecan-2-yl (2S)-2-formamido-4-methylpentanoate

• ChemBase ID: 179704
• Molecular Formular: C29H55NO4
• Molecular Mass: 481.7513
• Monoisotopic Mass: 481.41310925
• SMILES: C(=O)(O[C@H](C[C@@H]1OC[C@H]1CCCCCC)CCCCCCCCCCC)[C@H](CC(C)C)NC=O
• Canonical SMILES: CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC[C@H]1CCCCCC
• InChI: InChI=1S/C29H55NO4/c1-5-7-9-11-12-13-14-15-17-19-26(34-29(32)27(30-23-31)20-24(3)4)21-28-25(22-33-28)18-16-10-8-6-2/h23-28H,5-22H2,1-4H3,(H,30,31)/t25-,26+,27+,28+/m1/s1
• InChIKey: JILNSEQYEHCRJU-UNFRKHOWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S,3R)-3-hexyloxetan-2-yl]tridecan-2-yl (2S)-2-formamido-4-methylpentanoate
• IUPAC Traditional name: (2S)-1-[(2S,3R)-3-hexyloxetan-2-yl]tridecan-2-yl (2S)-2-formamido-4-methylpentanoate
• Synonyms: Tetrahydrolipstatin; Orlipastat; Orlistat (Tetrahydro)

Database IDs

• CAS Number: 96829-58-2
• PubChem SID: 164235614
• PubChem CID: 17571800

CALCULATED PROPERTIES

• Acid pKa: 12.91313
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 8.195009
• LogD (pH = 7.4): 8.195008
• Log P: 8.195009
• Molar Refractivity: 140.142 cm^3
• Polarizability: 56.077606 Å^3
• Polar Surface Area: 64.63 Å^2
• Rotatable Bonds: 23
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Pancreatic lipase inhibitor

Product Information

• Application(s): Used to treat obesity

REFERENCES

• Barbier, P. et al., Helv. Chim. Acta, 1987, 70, 196, (synth, abs config)
• Hogan, S. et al., Int. J. Obes., 1987, 11, 35, (pharmacol, deriv)
• Kupfer, E. et al., J. Antibiot., 1987, 40, 1081; 1086, (isol, struct, props)
• Hadvry, P. et al., Biochem. J., 1988, 256, 357, (pharmacol)
• Barbier, P. et al., J.O.C., 1988, 53, 1218, (synth, deriv, bibl)
• Fleming, I. et al., Tet. Lett., 1990, 31, 3645, (synth)
• Chadha, N.K. et al., J.O.C., 1991, 56, 4714, (synth)
• Hauptman, J.B. et al., Am. J. Clin. Nutr., 1992, 55, Suppl; 309S, (Orlipastat, pharmacol, human)
• Lthi-Peng, Q. et al., Eur. J. Biochem., 1992, 205, 383, (Orlipastat, pharmacol)
• Stalder, H. et al., Helv. Chim. Acta, 1992, 75, 1593, (Tetrahydrolipstatin, metab)
• Pommier, A. et al., Synthesis, 1994, 1294, (Tetrahydrolipstatin, synth)
• Pommier, A. et al., J.O.C., 1995, 60, 7334, (synth, bibl, pmr, cmr)
• McNeely, W. et al., Drugs, 1998, 56, 241-249, (rev)
• Ghosh, A.K. et al., Chem. Comm., 1999, 1743-1744, (synth, Tetrahydrolipstatin)
• Harp, J.B., Drugs of Today (Barcelona), 1999, 35, 139-145
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 1611
• Keating, G.M. et al., Drugs, 2001, 61, 2107-2119, (orlistat, rev)
• Goese, M. et al., J.O.C., 2001, 66, 4673-4678; 2002, 67, 2257-2262, (biosynth)