(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S,3S)-2-formamido-3-methylpentanoate

• ChemBase ID: 171811
• 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]([C@H](CC)C)NC=O)CCCCCCCCCCC)CCCCCC
• Canonical SMILES: CCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H]([C@H](CC)C)NC=O
• InChI: InChI=1S/C29H53NO5/c1-5-8-10-12-13-14-15-16-17-19-24(34-29(33)27(30-22-31)23(4)7-3)21-26-25(28(32)35-26)20-18-11-9-6-2/h22-27H,5-21H2,1-4H3,(H,30,31)/t23-,24-,25-,26-,27-/m0/s1
• InChIKey: CBHKWVNFZKJLIS-IRGGMKSGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S,3S)-2-formamido-3-methylpentanoate
• IUPAC Traditional name: (2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S,3S)-2-formamido-3-methylpentanoate
• Synonyms: N-Formyl-L-isoleucine (1S)-1-[[(2S,3S)-3-Hexyl-4-oxo-2-oxetanyl]methyl]dodecyl Ester; L-Isoleucine Orlistat

Database IDs

• CAS Number: 1072902-75-0
• PubChem SID: 164227721
• PubChem CID: 25140641

CALCULATED PROPERTIES

• Acid pKa: 12.695381
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 8.184531
• LogD (pH = 7.4): 8.184529
• Log P: 8.184531
• Molar Refractivity: 139.8673 cm^3
• Polarizability: 56.149376 Å^3
• Polar Surface Area: 81.7 Å^2
• Rotatable Bonds: 23
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - I820200

L-Isoleucine Orlistat is an impurity of Orlistat (O686500). Also, L-Isoleucine Orlistat is a Tetrahydrolipstatin (THL) analogue as inhibitor of the formation or hydrolysis of the endocannabinoid 2-arachidonoylglycerol (2-AG).

REFERENCES

• Mechoulam, R., et al.: Biochem. Pharmacol., 50, 83 (1995)
• Lambert, D., et al.: J. Med. Chem., 48, 5059 (1995)
• Ortar, G., et al.: J. Med. Chem., 51, 6970 (1995)