N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]hexacosanamide

• ChemBase ID: 167549
• Molecular Formular: C44H89NO3
• Molecular Mass: 680.18236
• Monoisotopic Mass: 679.68424571
• SMILES: C(C[C@H]([C@H](CO)NC(=O)CCCCCCCCCCCCCCCCCCCCCCCCC)O)CCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@@H](CCCCCCCCCCCCCCC)O)CO
• InChI: InChI=1S/C44H89NO3/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-28-30-32-34-36-38-40-44(48)45-42(41-46)43(47)39-37-35-33-31-29-27-16-14-12-10-8-6-4-2/h42-43,46-47H,3-41H2,1-2H3,(H,45,48)/t42-,43+/m0/s1
• InChIKey: NWERZHCPHDHUMO-WZYYJWNZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R)-1,3-dihydroxyoctadecan-2-yl]hexacosanamide
• IUPAC Traditional name: C26DH cer
• Synonyms: N-[(1S,2R)-2-Hydroxy-1-(hydroxymethyl)heptadecyl]hexacosanamide; [R-(R*,S*)]-N-[2-Hydroxy-1-(hydroxymethyl)heptadecyl]hexacosanamide; C26-Dihydroceramide; C26-Dihydro Ceramide

Database IDs

• CAS Number: 182362-38-5
• PubChem SID: 162261682
• PubChem CID: 644245

CALCULATED PROPERTIES

• Acid pKa: 13.831979
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 15.517055
• LogD (pH = 7.4): 15.5170555
• Log P: 15.517056
• Molar Refractivity: 210.8231 cm^3
• Polarizability: 84.28503 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 41
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D448780

A sphingolipid metabolite of mangrove endophytic fungus (No. 2534) from South China Sea.

REFERENCES

• Annesley, T., et al.: Clin. Chem., 49, 1041 (2003)
• Mongrand, S., et al.: J. Biol. Chem., 279, 36277 (2003)
• Markham, J., et al.: J. Biol. Chem., 281, 22684 (2003)