(2S,4Z,7Z)-1-[(2S,3R)-3-hexyl-4-oxooxetan-2-yl]trideca-4,7-dien-2-yl (2S)-2-formamido-4-methylpentanoate

• ChemBase ID: 172341
• Molecular Formular: C29H49NO5
• Molecular Mass: 491.70306
• Monoisotopic Mass: 491.36107367
• SMILES: [C@@H]1([C@H](C(=O)O1)CCCCCC)C[C@H](C/C=C\C/C=C\CCCCC)OC(=O)[C@H](CC(C)C)NC=O
• Canonical SMILES: CCCCC/C=C\C/C=C\C[C@@H](C[C@@H]1OC(=O)[C@@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O
• InChI: InChI=1S/C29H49NO5/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/h12-13,15-16,22-27H,5-11,14,17-21H2,1-4H3,(H,30,31)/b13-12-,16-15-/t24-,25+,26-,27-/m0/s1
• InChIKey: OQMAKWGYQLJJIA-MJASSXQFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4Z,7Z)-1-[(2S,3R)-3-hexyl-4-oxooxetan-2-yl]trideca-4,7-dien-2-yl (2S)-2-formamido-4-methylpentanoate
• IUPAC Traditional name: (2S,4Z,7Z)-1-[(2S,3R)-3-hexyl-4-oxooxetan-2-yl]trideca-4,7-dien-2-yl (2S)-2-formamido-4-methylpentanoate
• Synonyms: N-Formyl-L-leucine (1S,3Z,6Z)-1-[[(2S,3S)-3-Hexyl-4-oxo-2-oxetanyl]methyl]-3,6-dodecadien-1-yl Ester; N-Formyl-L-leucine [2S-[2α(1R*,3Z,6Z),3β]]-1-[(3-Hexyl-4-oxo-2-oxetanyl)methyl]-3,6-dodecadienyl Ester; (-)-Lipstatin; Lipstatin

Database IDs

• CAS Number: 96829-59-3
• PubChem SID: 164228251
• PubChem CID: 71749817

CALCULATED PROPERTIES

• Lipinski's Rule of Five: false
• Acid pKa: 12.728423
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 7.3827343
• LogD (pH = 7.4): 7.382733
• Log P: 7.3827343
• Molar Refractivity: 142.1775 cm^3
• Polarizability: 55.665848 Å^3
• Polar Surface Area: 81.7 Å^2
• Rotatable Bonds: 21

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Thick Yellow Oil

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - L468800

Lipstatin, a potent inhibitor of the pancreas lipase, is reported to be useful in the treatment and/or prevention of obesity and related diseases.

REFERENCES

• Derosa, G, et al.: Curr. Therap. Res., 63, 621 (2002)
• Skinner, D., et al.: J. Bacteriol., 177, 183 (2002)