(2S,3S,4R)-2-aminoicosane-1,3,4-triol

• ChemBase ID: 176472
• Molecular Formular: C20H43NO3
• Molecular Mass: 345.56032
• Monoisotopic Mass: 345.32429424
• SMILES: [C@@H]([C@H]([C@H](CO)N)O)(O)CCCCCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCC[C@H]([C@H]([C@H](CO)N)O)O
• InChI: InChI=1S/C20H43NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-19(23)20(24)18(21)17-22/h18-20,22-24H,2-17,21H2,1H3/t18-,19+,20-/m0/s1
• InChIKey: UQAUXYMLKGFKBX-ZCNNSNEGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4R)-2-aminoicosane-1,3,4-triol
• IUPAC Traditional name: (2S,3S,4R)-2-aminoicosane-1,3,4-triol
• Synonyms: (2S,3S,4R)-Amino-1,3,4-eicosanetriol; [2S-(2R*,3R*,4S*)]-2-Amino-1,3,4-eicosanetriol; 4D-Hydroxyeicosasphinganine; C20-Phytosphingosine; D-ribo-1,3,4-Trihydroxy-2-aminoeicosane; D-ribo C20-Phytosphingosine

Database IDs

• CAS Number: 3530-53-8
• PubChem SID: 164232382
• PubChem CID: 12302752

CALCULATED PROPERTIES

• Acid pKa: 13.447719
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 1.7062265
• LogD (pH = 7.4): 3.0778203
• Log P: 4.5868278
• Molar Refractivity: 101.4929 cm^3
• Polarizability: 40.952938 Å^3
• Polar Surface Area: 86.71 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P399050

D-ribo C20-Phytosphingosine is one of the principal sphingoid bases in plants, some fungi and marine organisms but are also present in mammalian tissues.

REFERENCES

• Sweeley, C., et al.: J. Lipid Res., 1, 40 (1959)
• Sperling, P., et al.: Eur. J. Biochem., 232, 798 (1959)
• Wells, G.B., et al.: J. Biol. Chem., 273, 7235 (1959)