(2S,3S,5S)-2-hexyl-3-hydroxy-5-{[(2S)-2-formamido-4-methylpentanoyl]oxy}hexadecanoic acid

• ChemBase ID: 169400
• Molecular Formular: C29H55NO6
• Molecular Mass: 513.7501
• Monoisotopic Mass: 513.40293849
• SMILES: C(CCCCCCCCC[C@@H](C[C@@H]([C@H](CCCCCC)C(=O)O)O)OC(=O)[C@H](CC(C)C)NC=O)C
• Canonical SMILES: CCCCCCCCCCC[C@@H](C[C@@H]([C@@H](C(=O)O)CCCCCC)O)OC(=O)[C@H](CC(C)C)NC=O
• InChI: InChI=1S/C29H55NO6/c1-5-7-9-11-12-13-14-15-16-18-24(36-29(35)26(30-22-31)20-23(3)4)21-27(32)25(28(33)34)19-17-10-8-6-2/h22-27,32H,5-21H2,1-4H3,(H,30,31)(H,33,34)/t24-,25-,26-,27-/m0/s1
• InChIKey: FKUNIADJSAJLGB-FWEHEUNISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,5S)-2-hexyl-3-hydroxy-5-{[(2S)-2-formamido-4-methylpentanoyl]oxy}hexadecanoic acid
• IUPAC Traditional name: (2S,3S,5S)-2-hexyl-3-hydroxy-5-{[(2S)-2-formamido-4-methylpentanoyl]oxy}hexadecanoic acid
• Synonyms: N-Formyl-L-leucine(1S)-1-[(2S,3S)-3-carboxy-2-hydroxynonyl]dodecyl Ester; 5-(Formamido-4-methylpentanoyloxy)-2-hexyl-3-hydroxyhexadecanoic Acid; Orlistat Impurity M1; (2S,3S,5S)-5-[(N-Formyl-L-leucyl)oxy]-2-hexyl-3-hydroxyhexadecanoic Acid(Orlistat Impurity)

Database IDs

• CAS Number: 130676-66-3
• PubChem SID: 162263532
• PubChem CID: 14607536

CALCULATED PROPERTIES

• Acid pKa: 4.465407
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 6.3705397
• LogD (pH = 7.4): 4.6053624
• Log P: 7.4421067
• Molar Refractivity: 143.4365 cm^3
• Polarizability: 57.25109 Å^3
• Polar Surface Area: 112.93 Å^2
• Rotatable Bonds: 25
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Colourless Thick Oil

Safety Information

• Storage Condition: -86°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - F700600

A metabolite of Orlistat (O686500).

REFERENCES

• Stalder, H., et al.: Helv. Chimica Acta, 75, 1593 (1992)