(2R,3S,4E)-2-{[(tert-butoxy)carbonyl]amino}-1-hydroxyoctadec-4-en-3-yl benzoate

• ChemBase ID: 161306
• Molecular Formular: C30H49NO5
• Molecular Mass: 503.71376
• Monoisotopic Mass: 503.36107367
• SMILES: OC[C@H]([C@H](/C=C/CCCCCCCCCCCCC)OC(=O)c1ccccc1)NC(=O)OC(C)(C)C
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@@H]([C@H](NC(=O)OC(C)(C)C)CO)OC(=O)c1ccccc1
• InChI: InChI=1S/C30H49NO5/c1-5-6-7-8-9-10-11-12-13-14-15-16-20-23-27(35-28(33)25-21-18-17-19-22-25)26(24-32)31-29(34)36-30(2,3)4/h17-23,26-27,32H,5-16,24H2,1-4H3,(H,31,34)/b23-20+/t26-,27+/m1/s1
• InChIKey: GJCJNLOYMRJWLR-GLPSRTLHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4E)-2-{[(tert-butoxy)carbonyl]amino}-1-hydroxyoctadec-4-en-3-yl benzoate
• IUPAC Traditional name: (2R,3S,4E)-2-[(tert-butoxycarbonyl)amino]-1-hydroxyoctadec-4-en-3-yl benzoate
• Synonyms: N-[(1S,2R,3E)-2-(Benzoyloxy)-1-(hydroxymethyl)-3-heptadecen-1-yl]carbamic Acid 1,1-Dimethylethyl Ester; (2S,3R,4E)-3-Benzoyl-2-tert-butyloxycarbonylamino-4-octadecen-1,3-diol

Database IDs

• CAS Number: 299172-59-1
• PubChem SID: 162255441
• PubChem CID: 71313715

CALCULATED PROPERTIES

• Acid pKa: 13.705868
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 8.553977
• LogD (pH = 7.4): 8.553977
• Log P: 8.553977
• Molar Refractivity: 146.587 cm^3
• Polarizability: 57.541935 Å^3
• Polar Surface Area: 84.86 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Crystalline Solid

REFERENCES

• Kinjo, Y., et al.: Chem. Biol., 15, 654 (2008)