(15Z)-N-[(3S,4R)-1-{[(2S,4S,5R)-6-(acetamidomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxyoctadecan-2-yl]tetracos-15-enamide

• ChemBase ID: 176240
• Molecular Formular: C50H96N2O9
• Molecular Mass: 869.30524
• Monoisotopic Mass: 868.71158266
• SMILES: C(CCCCCCCCCCCCC)[C@H]([C@H](C(NC(=O)CCCCCCCCCCCCC/C=C\CCCCCCCC)CO[C@H]1OC([C@@H]([C@@H](C1O)O)O)CNC(=O)C)O)O
• Canonical SMILES: CCCCCCCCCCCCCC[C@H]([C@H](C(NC(=O)CCCCCCCCCCCCC/C=C\CCCCCCCC)CO[C@H]1OC(CNC(=O)C)[C@@H]([C@@H](C1O)O)O)O)O
• InChI: InChI=1S/C50H96N2O9/c1-4-6-8-10-12-14-16-18-19-20-21-22-23-24-25-26-28-30-32-34-36-38-45(55)52-42(40-60-50-49(59)48(58)47(57)44(61-50)39-51-41(3)53)46(56)43(54)37-35-33-31-29-27-17-15-13-11-9-7-5-2/h18-19,42-44,46-50,54,56-59H,4-17,20-40H2,1-3H3,(H,51,53)(H,52,55)/b19-18-/t42?,43-,44?,46+,47+,48+,49?,50+/m1/s1
• InChIKey: LIXVHWQNKBIZBR-IZJXYXLGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (15Z)-N-[(3S,4R)-1-{[(2S,4S,5R)-6-(acetamidomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxyoctadecan-2-yl]tetracos-15-enamide
• IUPAC Traditional name: (15Z)-N-[(3S,4R)-1-{[(2S,4S,5R)-6-(acetamidomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxyoctadecan-2-yl]tetracos-15-enamide
• Synonyms: (15Z)-N-[(1S,2S,3R)-1-[[[6-(Acetylamino)-6-deoxy-α-D-galactopyranosyl]oxy]methyl]-2,3-dihydroxyheptadecyl]-15-tetracosenamide; PBS 57

Database IDs

• CAS Number: 898531-99-2
• PubChem SID: 164232150
• PubChem CID: 71751470

CALCULATED PROPERTIES

• Acid pKa: 12.163405
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): 11.132221
• LogD (pH = 7.4): 11.1322155
• Log P: 11.132222
• Molar Refractivity: 247.6138 cm^3
• Polarizability: 98.74592 Å^3
• Polar Surface Area: 177.81 Å^2
• Rotatable Bonds: 42
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P215300

A galactosylceramide derivative used in the treatment of influenza. PBS-57 has the ability to stimulate both a cell-mediated and humoral immune response. Co-administration of PBS-57 with a vaccine may be used in methods to stimulate one or more of a humor

REFERENCES

• Liu, Y., et al.: J. Immunol. Methods, 312, 34 (2006)
• Kamijuku, H., et al.: Mucosal Immunology, 1, 208 (2006)
• Kopecky-Bromberg, S; Vaccine, 27, 3766 (2006)