(2S,3R,4E)-2-azido-1-[(2,2-dimethylpropanoyl)oxy]octadec-4-en-3-yl 2,2-dimethylpropanoate

• ChemBase ID: 161018
• Molecular Formular: C28H51N3O4
• Molecular Mass: 493.72224
• Monoisotopic Mass: 493.38795713
• SMILES: O(C[C@@H]([C@@H](/C=C/CCCCCCCCCCCCC)OC(=O)C(C)(C)C)N=[N+]=[N-])C(=O)C(C)(C)C
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](COC(=O)C(C)(C)C)N=[N+]=[N-])OC(=O)C(C)(C)C
• InChI: InChI=1S/C28H51N3O4/c1-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(35-26(33)28(5,6)7)23(30-31-29)22-34-25(32)27(2,3)4/h20-21,23-24H,8-19,22H2,1-7H3/b21-20+/t23-,24+/m0/s1
• InChIKey: JLUIQNXSWIOAHS-UVAUYHEJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4E)-2-azido-1-[(2,2-dimethylpropanoyl)oxy]octadec-4-en-3-yl 2,2-dimethylpropanoate
• IUPAC Traditional name: (2S,3R,4E)-2-azido-1-[(2,2-dimethylpropanoyl)oxy]octadec-4-en-3-yl 2,2-dimethylpropanoate
• Synonyms: (2S,3R,4E)-2-Azido-1,3-di-o-pivaloyl-4-octadecene-3-ol; 2-Azido-1,3-di-o-pivaloyl D-erythro-Sphingosine

Database IDs

• PubChem SID: 162255153
• PubChem CID: 46780532

CALCULATED PROPERTIES

• Acid pKa: 16.11852
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 9.861084
• LogD (pH = 7.4): 9.861084
• Log P: 9.97513
• Molar Refractivity: 142.2348 cm^3
• Polarizability: 55.84222 Å^3
• Polar Surface Area: 82.03 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Hexane
• Apperance: Colourless Oil

DETAILS

Toronto Research Chemicals - A847625

A derivative of Sphingosine, a selective inhibitor of protein kinase C activity and phorbol dibutyrate binding in vitro in human platelets; does not inhibit protein kinase A or myosin light chain kinase; inhibits calmodulin-dependent enzymes; natural isom