(2S,3R,4E)-2-azido-3-hydroxyoctadec-4-en-1-yl 2,2-dimethylpropanoate

• ChemBase ID: 161078
• Molecular Formular: C23H43N3O3
• Molecular Mass: 409.60582
• Monoisotopic Mass: 409.33044225
• SMILES: O(C[C@@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)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-])O
• InChI: InChI=1S/C23H43N3O3/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-21(27)20(25-26-24)19-29-22(28)23(2,3)4/h17-18,20-21,27H,5-16,19H2,1-4H3/b18-17+/t20-,21+/m0/s1
• InChIKey: HBQMTKUQTNSGBI-BWMVHVDHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4E)-2-azido-3-hydroxyoctadec-4-en-1-yl 2,2-dimethylpropanoate
• IUPAC Traditional name: (2S,3R,4E)-2-azido-3-hydroxyoctadec-4-en-1-yl 2,2-dimethylpropanoate
• Synonyms: [R-[R*,S*-(E)]]-2,2-Dimethyl-propanoic Acid 2-Azido-3-hydroxy-4-octadecenyl Ester; (2S,3R,4E)-2-Azido-1-pivaloyloxy-4-octadecene-3-ol; 2-Azido-1-pivaloyl D-erythro-Sphingosine

Database IDs

• CAS Number: 114275-41-1
• PubChem SID: 162255213
• PubChem CID: 14101935

CALCULATED PROPERTIES

• Lipinski's Rule of Five: false
• Acid pKa: 13.957678
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 7.6204224
• LogD (pH = 7.4): 7.6204224
• Log P: 7.734468
• Molar Refractivity: 119.3809 cm^3
• Polarizability: 46.48783 Å^3
• Polar Surface Area: 75.96 Å^2
• Rotatable Bonds: 19

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; Methanol
• Apperance: Colourless Oil

DETAILS

Toronto Research Chemicals - A925080

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