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

• ChemBase ID: 160410
• Molecular Formular: C18H27NO11
• Molecular Mass: 433.40708
• Monoisotopic Mass: 433.15841069
• SMILES: c1c(ccc(c1)OC1[C@@H]([C@H]([C@@H]([C@H](O1)CO)OC1O[C@@H]([C@@H]([C@@H]([C@H]1O)O)O)CO)O)O)N
• Canonical SMILES: OC[C@H]1OC(Oc2ccc(cc2)N)[C@@H]([C@H]([C@@H]1OC1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O)O)O)O
• InChI: InChI=1S/C18H27NO11/c19-7-1-3-8(4-2-7)27-17-15(26)13(24)16(10(6-21)29-17)30-18-14(25)12(23)11(22)9(5-20)28-18/h1-4,9-18,20-26H,5-6,19H2/t9-,10-,11+,12+,13-,14-,15-,16-,17?,18?/m1/s1
• InChIKey: OCHWUNNDLIWPAO-NJRVNMCVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5R,6R)-2-{[(2R,3S,4R,5R)-6-(4-aminophenoxy)-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (3R,4S,5R,6R)-2-{[(2R,3S,4R,5R)-6-(4-aminophenoxy)-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: p-Aminophenyl β-lactoside; p-Aminophenyl β-D-Lactopyranoside; 4-Aminophenyl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside; 4-Aminophenyl β-D-lactopyranoside

Database IDs

• CAS Number: 17691-02-0
• PubChem SID: 162254545
• PubChem CID: 45038146

CALCULATED PROPERTIES

• Acid pKa: 11.934123
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -3.2676773
• LogD (pH = 7.4): -3.199111
• Log P: -3.1981492
• Molar Refractivity: 97.297 cm^3
• Polarizability: 39.56285 Å^3
• Polar Surface Area: 204.55 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Off-White Solid
• Melting Point: 234-236°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A624700

A useful artificial carbohydrate protein conjugate that can be used as an antigen or immunogen.

REFERENCES

• Roy, R., et al.: J. Chem Soc. Chem. Commun., 536 - 538 (1991)