(2R,3R,4S,5R)-2-(acetyloxy)-4-(benzoyloxy)-5-[(benzoyloxy)(13C)methyl](2,3,4,5-13C4)oxolan-3-yl benzoate

• ChemBase ID: 159508
• Molecular Formular: C28H24O9
• Molecular Mass: 509.44803419
• Monoisotopic Mass: 509.15880654
• SMILES: [13C@H]1([13C@@H]([13CH2]OC(=O)c2ccccc2)O[13C@H]([13C@@H]1OC(=O)c1ccccc1)OC(=O)C)OC(=O)c1ccccc1
• Canonical SMILES: CC(=O)O[13C@@H]1O[13C@@H]([13C@H]([13C@H]1OC(=O)c1ccccc1)OC(=O)c1ccccc1)[13CH2]OC(=O)c1ccccc1
• InChI: InChI=1S/C28H24O9/c1-18(29)34-28-24(37-27(32)21-15-9-4-10-16-21)23(36-26(31)20-13-7-3-8-14-20)22(35-28)17-33-25(30)19-11-5-2-6-12-19/h2-16,22-24,28H,17H2,1H3/t22-,23-,24-,28-/m1/s1/i17+1,22+1,23+1,24+1,28+1
• InChIKey: GCZABPLTDYVJMP-CZGJTPJASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-(acetyloxy)-4-(benzoyloxy)-5-[(benzoyloxy)(^1^3C)methyl](2,3,4,5-^1^3C₄)oxolan-3-yl benzoate
• IUPAC Traditional name: (2R,3R,4S,5R)-2-(acetyloxy)-4-(benzoyloxy)-5-[(benzoyloxy)(^1^3C)methyl](2,3,4,5-^1^3C₄)oxolan-3-yl benzoate
• Synonyms: β-D-Ribofuranose-13C5 1-Αcetate 2,3,5-Tribenzoate; 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribose-13C5; 2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl-13C5 Acetate; ABR-13C5; NSC 23349-13C5; 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose-13C5

Database IDs

• PubChem SID: 162253643
• PubChem CID: 71313013

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 5.6248207
• LogD (pH = 7.4): 5.6248207
• Log P: 5.6248207
• Molar Refractivity: 128.5784 cm^3
• Polarizability: 50.93317 Å^3
• Polar Surface Area: 114.43 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate,
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - A189332

A labelled inhibitor of neutrophil-keyhole limpet hemocyanin adhesion. Anti-inflammatory agent.

REFERENCES

• Shappell, S., et al.: J. Immunol., 144, 2702 (1990)
• Ross, L., et al.: J. Biol. Chem., 267, 8537 (1990)
• Granger, D., et al.: J. Leukoc. Biol., 55, 662 (1990)