(2S,3R)-2-amino-15-methylhexadecane-1,3-diol

• ChemBase ID: 173766
• Molecular Formular: C17H37NO2
• Molecular Mass: 287.48118
• Monoisotopic Mass: 287.28242943
• SMILES: [C@@H]([C@H](CO)N)(O)CCCCCCCCCCCC(C)C
• Canonical SMILES: OC[C@@H]([C@@H](CCCCCCCCCCCC(C)C)O)N
• InChI: InChI=1S/C17H37NO2/c1-15(2)12-10-8-6-4-3-5-7-9-11-13-17(20)16(18)14-19/h15-17,19-20H,3-14,18H2,1-2H3/t16-,17+/m0/s1
• InChIKey: VFYHIOGWELBGIK-DLBZAZTESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-2-amino-15-methylhexadecane-1,3-diol
• IUPAC Traditional name: (2S,3R)-2-amino-15-methylhexadecane-1,3-diol
• Synonyms: [R-(R*,S*)]-2-Amino-15-methyl-1,3-hexadecanediol; D-erythro- 2-Amino-15-methyl-1,3-hexadecanediol; D-erythro-C17-iso-Sphinganine; 15-Methylhexadeca Sphinganine

Database IDs

• CAS Number: 26048-10-2
• PubChem SID: 164229676
• PubChem CID: 70679000

CALCULATED PROPERTIES

• Acid pKa: 14.419876
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 1.2076713
• LogD (pH = 7.4): 2.3071373
• Log P: 4.170476
• Molar Refractivity: 86.276 cm^3
• Polarizability: 34.81673 Å^3
• Polar Surface Area: 66.48 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 58-61°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M311970

The major sphinganine from the ceramides phospholipids of Bacteroides melaninogenicus as arachidonate cascade inhibitor and blood platelet aggregation inhibitor.

REFERENCES

• Dennis, R., et al.: Eur. J. Biochem., 146, 51 (1985)
• Dennis, R., et al.: J. Biol. Chem., 260,, 5370 (1985)
• Field, K., et al.: Science, 239, 748 (1985)