[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]trimethylazanium chloride

• ChemBase ID: 179259
• Molecular Formular: C21H44ClNO2
• Molecular Mass: 378.03256
• Monoisotopic Mass: 377.30605733
• SMILES: OC[C@@H]([C@@H](/C=C/CCCCCCCCCCCCC)O)[N+](C)(C)C.[Cl-]
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@@H]([N+](C)(C)C)CO)O.[Cl-]
• InChI: InChI=1S/C21H44NO2.ClH/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-21(24)20(19-23)22(2,3)4;/h17-18,20-21,23-24H,5-16,19H2,1-4H3;1H/q+1;/p-1/b18-17+;/t20-,21+;/m0./s1
• InChIKey: OBTLGDGOHFHYNH-DSQFUKAXSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]trimethylazanium chloride
• IUPAC Traditional name: N,N,N-trimethyl-sphingosine chloride
• Synonyms: [R-[R*,S*-(E)]]-1,3-Dihydroxy-N,N,N-trimethyl-4-octadecen-2-aminium Chloride; D-erythro-N,N,N-Trimethylsphingosine Chloride

Database IDs

• CAS Number: 134962-48-4
• PubChem SID: 164235169
• PubChem CID: 14889582

CALCULATED PROPERTIES

• Acid pKa: 12.772933
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.2198722
• LogD (pH = 7.4): 1.2199067
• Log P: 1.2198718
• Molar Refractivity: 117.8749 cm^3
• Polarizability: 41.890606 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 72-74°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Store in Freezer

DETAILS

Toronto Research Chemicals - T797150

Has an inhibitory effect via blocking of transmembrane signaling on the growth of various human tumor cell lines in vitro as well as in vivo in nu/nu mice. A potent and effective cardioprotective agent that inhibits leukocyte-endothelial cell interaction

REFERENCES

• Handa, K., et al.: Biochemistry, 30, 50, 11684 (1991)
• Endo, K., et al.: Cancer Research, 51, 1613 (1991)
• Park, Y.S., et al.: Cancer Research, 54, 2213 (1991)
• Kennedy, S.D., et al.: Am. J. Clin. Pathol., 107, 1, 99 (1991)
• Campbell, B., et al: Cardivasc