N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]butanamide

• ChemBase ID: 163511
• Molecular Formular: C22H45NO4
• Molecular Mass: 387.597
• Monoisotopic Mass: 387.33485893
• SMILES: C(CC[C@H]([C@H]([C@H](CO)NC(=O)CCC)O)O)CCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCC[C@H]([C@H]([C@@H](NC(=O)CCC)CO)O)O
• InChI: InChI=1S/C22H45NO4/c1-3-5-6-7-8-9-10-11-12-13-14-15-17-20(25)22(27)19(18-24)23-21(26)16-4-2/h19-20,22,24-25,27H,3-18H2,1-2H3,(H,23,26)/t19-,20+,22-/m0/s1
• InChIKey: CRVGCEIWUOFGLZ-VWPQPMDRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]butanamide
• IUPAC Traditional name: N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]butanamide
• Synonyms: N-Butyroyl Phytosphingosine; N-[(1S,2S,3R)-2,3-Dihydroxy-1-(hydroxymethyl)heptadecyl]butanamide; C4-Phytoceramide

Database IDs

• CAS Number: 409085-57-0
• PubChem SID: 162257646
• PubChem CID: 71314462

CALCULATED PROPERTIES

• Acid pKa: 13.239937
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 4.661641
• LogD (pH = 7.4): 4.661641
• Log P: 4.6616416
• Molar Refractivity: 110.9626 cm^3
• Polarizability: 44.314274 Å^3
• Polar Surface Area: 89.79 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 79-81°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - B802515

An intermediate in the syntheses of all stereoisomers of phytosphingosine as ceramides.

REFERENCES

• Perry, D., et al.: Biochim. Biophys Acta, 1436, 233 (1998)
• Chang, Y., et al.: Bioorg. Med. Chem. Lett., 9, 2479 (1998)
• Prieschl, E., et al.: J. Immunol., 164, 5389 (1998)