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

• ChemBase ID: 175920
• 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-NFGXINMFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2R)-2-formamido-4-methylpentanoate
• IUPAC Traditional name: (2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2R)-2-formamido-4-methylpentanoate
• Synonyms: N-Formyl-D-leucine (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl Ester; [2S-[2α(R*),3β]]-N-Formyl-D-leucine 1-[(3-Hexyl-4-oxo-2-oxetanyl)methyl]dodecyl Ester; (R,S,S,S)-Orlistat

Database IDs

• CAS Number: 104872-28-8
• PubChem SID: 164231830
• PubChem CID: 13817938

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

DETAILS

Toronto Research Chemicals - O686480

An isomeric impurity of Orlistat (O686500) with modulatory activity on endocannabinoid 2-arachidonoylglycerol metabolism.

REFERENCES

• Ortar, G. et al.: J. Med. Chem., 51, 6970 (2008)