7-{[(2S,3R,4S,5S,6S)-6-[(hexadecanoylsulfanyl)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4-methyl-2H-chromen-2-one

• ChemBase ID: 174538
• Molecular Formular: C32H48O8S
• Molecular Mass: 592.78372
• Monoisotopic Mass: 592.3069895
• SMILES: O1[C@@H](Oc2cc3c(cc2)c(cc(=O)o3)C)[C@H]([C@H]([C@@H]([C@@H]1CSC(=O)CCCCCCCCCCCCCCC)O)O)O
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)SC[C@@H]1O[C@@H](Oc2ccc3c(c2)oc(=O)cc3C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C32H48O8S/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-28(34)41-21-26-29(35)30(36)31(37)32(40-26)38-23-17-18-24-22(2)19-27(33)39-25(24)20-23/h17-20,26,29-32,35-37H,3-16,21H2,1-2H3/t26-,29-,30+,31-,32-/m1/s1
• InChIKey: XCNUAQFXJPMZLU-GEBXWWPGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-{[(2S,3R,4S,5S,6S)-6-[(hexadecanoylsulfanyl)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4-methyl-2H-chromen-2-one
• IUPAC Traditional name: 7-{[(2S,3R,4S,5S,6S)-6-[(hexadecanoylsulfanyl)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-4-methylchromen-2-one
• Synonyms: 4-Methyl-7-[[6-S-(1-oxohexadecyl)-6-thio-β-D-glucopyranosyl]oxy]- 2H-1-benzopyran-2-one; Mu-6S-Palm-β-Glc; 4-Methylumbelliferyl 6-Thio-palmitate-β-D-glucopyranoside

Database IDs

• CAS Number: 229644-17-1
• PubChem SID: 164230448
• PubChem CID: 71750703

CALCULATED PROPERTIES

• Acid pKa: 12.208634
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 6.927119
• LogD (pH = 7.4): 6.927112
• Log P: 6.927119
• Molar Refractivity: 160.0462 cm^3
• Polarizability: 63.747837 Å^3
• Polar Surface Area: 122.52 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: Off-White Solid
• Melting Point: 123-125°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M336675

A fluorogenic substrate for the assay of Palmitoyl-Protein Thioesterase, used in the diagnosis of infantile neuronal ceroid lipofuscinosis (INCL).

REFERENCES

• Goebel, H., et al.: J. Child Neurol., 10, 424 (1995)
• Verkruyse, L., et al.: J. Biol. Chem., 271, 15831 (1995)
• Sleat, D., et al.: Science, 277, 1802 (1995)
• Cho, S., et aL.: J. Neurochem., 71, 323 (1995)