(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S)-2-{[(benzyloxy)carbonyl]amino}-4-methylpentanoate

• ChemBase ID: 165583
• Molecular Formular: C36H59NO6
• Molecular Mass: 601.85676
• Monoisotopic Mass: 601.43423861
• SMILES: C1(=O)O[C@H]([C@@H]1CCCCCC)C[C@@H](OC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1)CCCCCCCCCCC
• Canonical SMILES: CCCCCC[C@@H]1C(=O)O[C@H]1C[C@@H](OC(=O)[C@@H](NC(=O)OCc1ccccc1)CC(C)C)CCCCCCCCCCC
• InChI: InChI=1S/C36H59NO6/c1-5-7-9-11-12-13-14-15-19-23-30(26-33-31(34(38)43-33)24-20-10-8-6-2)42-35(39)32(25-28(3)4)37-36(40)41-27-29-21-17-16-18-22-29/h16-18,21-22,28,30-33H,5-15,19-20,23-27H2,1-4H3,(H,37,40)/t30-,31-,32-,33-/m0/s1
• InChIKey: OITCZADOYPEICM-YRCZKMHPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S)-2-{[(benzyloxy)carbonyl]amino}-4-methylpentanoate
• IUPAC Traditional name: (2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S)-2-{[(benzyloxy)carbonyl]amino}-4-methylpentanoate
• Synonyms: N-[(Phenylmethoxy)carbonyl]-L-Leucine (1S)-1-[[(2S,3S)-3-Hexyl-4-oxo-2-oxetanyl]methyl]dodecyl Ester; N-Deformyl-N-benzyloxycarbonyl Orlistat

Database IDs

• CAS Number: 108051-94-1
• PubChem SID: 162259716
• PubChem CID: 14847017

CALCULATED PROPERTIES

• Acid pKa: 13.434695
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 10.499041
• LogD (pH = 7.4): 10.499041
• Log P: 10.499041
• Molar Refractivity: 170.671 cm^3
• Polarizability: 68.27324 Å^3
• Polar Surface Area: 90.93 Å^2
• Rotatable Bonds: 26
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D229050

Orlistat analogue.

REFERENCES

• Weibel, E., et al.: J. Antibiot., 40, 1081 ( 1987), Lookene, A., et al.: J. Biochem., 222, 395 (1994)