(2S,3S,4R,5S,6S)-2-{[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

• ChemBase ID: 175172
• Molecular Formular: C18H25NO12
• Molecular Mass: 447.3906
• Monoisotopic Mass: 447.13767525
• SMILES: [C@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)Oc1ccc(cc1)[N+](=O)[O-])O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C)O)O)O)O)O
• Canonical SMILES: OC[C@@H]1O[C@@H](Oc2ccc(cc2)[N+](=O)[O-])[C@H]([C@H]([C@H]1O)O)O[C@@H]1O[C@@H](C)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C18H25NO12/c1-7-11(21)13(23)15(25)17(28-7)31-16-14(24)12(22)10(6-20)30-18(16)29-9-4-2-8(3-5-9)19(26)27/h2-5,7,10-18,20-25H,6H2,1H3/t7-,10+,11+,12-,13+,14-,15-,16+,17-,18+/m0/s1
• InChIKey: FMNXEBSKDAQHBI-YUXDDOTLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4R,5S,6S)-2-{[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol
• IUPAC Traditional name: (2S,3S,4R,5S,6S)-2-{[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol
• Synonyms: Fuc1-α-2Gal-β-PNP; p-Nitrophenyl 2-O-(α-L-fucopyranosyl)-β-D-galactopyranoside

Database IDs

• CAS Number: 66347-27-1
• PubChem SID: 164231082
• PubChem CID: 196440

CALCULATED PROPERTIES

• Acid pKa: 12.10016
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -1.3823292
• LogD (pH = 7.4): -1.3823377
• Log P: -1.3823291
• Molar Refractivity: 98.3776 cm^3
• Polarizability: 39.75317 Å^3
• Polar Surface Area: 204.12 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Warm Methanol
• Apperance: White Amorphous Solid
• Melting Point: 253-254°C dec.

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N503555

A synthetic chromogenic substrate for the assay of a-fucosidases.

REFERENCES

• DiCioccio, R.A., et al.: Anal. Biochem., 11, 176 (1981)