(2S,3R,4E)-2-aminotetradec-4-ene-1,3-diol

• ChemBase ID: 160488
• Molecular Formular: C14H29NO2
• Molecular Mass: 243.38556
• Monoisotopic Mass: 243.21982917
• SMILES: C(CCCCCCC/C=C/[C@H]([C@H](CO)N)O)C
• Canonical SMILES: CCCCCCCCC/C=C/[C@H]([C@H](CO)N)O
• InChI: InChI=1S/C14H29NO2/c1-2-3-4-5-6-7-8-9-10-11-14(17)13(15)12-16/h10-11,13-14,16-17H,2-9,12,15H2,1H3/b11-10+/t13-,14+/m0/s1
• InChIKey: VDRZDTXJMRRVMF-NXFSIWHZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4E)-2-aminotetradec-4-ene-1,3-diol
• IUPAC Traditional name: (4E,d14:1) sphingosine
• Synonyms: (E)-D-erythro-2-Amino-4-tetradecene-1,3-diol; C14-Sphingosine; Tetradecasphing-4-enine; (2S,3R,4E)-2-Amino-4-tetradecene-1,3-diol

Database IDs

• CAS Number: 24558-60-9
• PubChem SID: 162254623
• PubChem CID: 42608342

CALCULATED PROPERTIES

• Acid pKa: 14.11614
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.16609806
• LogD (pH = 7.4): 0.9742237
• Log P: 2.7883053
• Molar Refractivity: 73.488 cm^3
• Polarizability: 29.04502 Å^3
• Polar Surface Area: 66.48 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - A629650

Sphingosine base present in crayfish and drosophila, contributing to muscle degeneration

REFERENCES

• Kita, K., et al.: Eur. J. Biochem., 268, 592 (2001)
• Fyrst, H., et al.: J. Lipid Res., 49, 597 (2001)