(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S)-2-formamido-4-methyl(5,5,5-2H3)pentanoate

• ChemBase ID: 175924
• Molecular Formular: C29H53NO5
• Molecular Mass: 495.73482
• Monoisotopic Mass: 495.3923738
• SMILES: C1(=O)[C@H]([C@@H](O1)C[C@@H](OC(=O)[C@H](CC(C)C)NC=O)CCCCCCCCCCC)CCCCCC
• Canonical SMILES: CCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O
• InChI: InChI=1S/C29H53NO5/c1-5-7-9-11-12-13-14-15-16-18-24(34-29(33)26(30-22-31)20-23(3)4)21-27-25(28(32)35-27)19-17-10-8-6-2/h22-27H,5-21H2,1-4H3,(H,30,31)/t24-,25-,26-,27-/m0/s1
• InChIKey: AHLBNYSZXLDEJQ-FWEHEUNISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S)-2-formamido-4-methyl(5,5,5-^2H₃)pentanoate
• IUPAC Traditional name: (2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S)-2-formamido-4-methyl(5,5,5-^2H₃)pentanoate
• Synonyms: N-Formyl-L-leucine (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl Ester-d3; (-)-Tetrahydrolipstatin-d3; Ro 18-0647/002-d3; Tetrahydrolipstatin-d3; Xenical-d3; Orlistat-d3

Database IDs

• PubChem SID: 164231834
• PubChem CID: 46782633

CALCULATED PROPERTIES

• Acid pKa: 12.743767
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 8.106578
• LogD (pH = 7.4): 8.106576
• Log P: 8.106578
• Molar Refractivity: 139.9443 cm^3
• Polarizability: 56.149376 Å^3
• Polar Surface Area: 81.7 Å^2
• Rotatable Bonds: 23
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White to Light Tan Solid
• Melting Point: 39-41°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - O686502

Labelled Orlistat, an antiobesity agent. Orlistat is a pancreatic lipase inhibitor.

REFERENCES

• Borgstrom, B., et al.: Biochim. Biophys. Acta, 962, 308 (1988)
• Hauptman, J.B., et al.: Am. J. Clin. Nutr., 55, 309S (1988)
• McNeely, W., et al.: Drugs, 56, 241 (1988)
• Hauptman, J. B., et al.: Arch. Fam. Med., 9, 160 (1988)