methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(1S,10R,11S,14S,15S)-5-(acetyloxy)-14-ethynyl-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-trien-14-yl]oxy}oxane-2-carboxylate

• ChemBase ID: 178196
• Molecular Formular: C35H42O12
• Molecular Mass: 654.70078
• Monoisotopic Mass: 654.26762678
• SMILES: c1c(cc2c(c1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@](CC2)(C#C)O[C@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)C(=O)OC)OC(=O)C)OC(=O)C)OC(=O)C)C)OC(=O)C
• Canonical SMILES: C#C[C@]1(CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)OC(=O)C)O[C@@H]1O[C@H](C(=O)OC)[C@H]([C@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C35H42O12/c1-8-35(47-33-31(45-21(5)39)29(44-20(4)38)28(43-19(3)37)30(46-33)32(40)41-7)16-14-27-26-11-9-22-17-23(42-18(2)36)10-12-24(22)25(26)13-15-34(27,35)6/h1,10,12,17,25-31,33H,9,11,13-16H2,2-7H3/t25-,26-,27+,28+,29+,30+,31-,33+,34+,35-/m1/s1
• InChIKey: WSARSYAEMGZMDS-VHPSLLQTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(1S,10R,11S,14S,15S)-5-(acetyloxy)-14-ethynyl-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-14-yl]oxy}oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(1S,10R,11S,14S,15S)-5-(acetyloxy)-14-ethynyl-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-14-yl]oxy}oxane-2-carboxylate
• Synonyms: 1,2,3,4-Τetraacetate 6-(Diphenyl phosphate) β-D-Mannopyranose; 1,2,3,4-Tetra-O-acetyl-6-diphenylphosphoryl-β-D-mannopyranose

Database IDs

• CAS Number: 108321-48-8
• PubChem SID: 164234106
• PubChem CID: 71752383

CALCULATED PROPERTIES

• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 3.8268886
• LogD (pH = 7.4): 3.8268886
• Log P: 3.8268886
• Molar Refractivity: 161.0303 cm^3
• Polarizability: 64.93183 Å^3
• Polar Surface Area: 149.96 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 113-115°C

DETAILS

Toronto Research Chemicals - T278750

D-Mannose 6-phosphate residues on asparagine-linked oligosaccharide chains are known as subcellular sorting signals in the lysosomal targeting of acid hydrolases.

REFERENCES

• Sahagian, G.G.: Biol. Cell., 51, 207 (1984) Creek, K.E., et al.: Lysosomes Biol. Pathol., 7, 63 (1984)
• Lang, L., et al.: J. Biol. Chem., 259 (1984)