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

• ChemBase ID: 160413
• Molecular Formular: C18H27NO11
• Molecular Mass: 433.40708
• Monoisotopic Mass: 433.15841069
• SMILES: [C@@H]1([C@@H](C([C@H](OC1CO)O[C@H]1[C@@H](C(O[C@@H](C1O)Oc1ccc(cc1)N)CO)O)O)O)O
• Canonical SMILES: OCC1O[C@H](Oc2ccc(cc2)N)C([C@H]([C@@H]1O)O[C@H]1OC(CO)[C@H]([C@@H](C1O)O)O)O
• InChI: InChI=1S/C18H27NO11/c19-7-1-3-8(4-2-7)27-18-15(26)16(12(23)10(6-21)29-18)30-17-14(25)13(24)11(22)9(5-20)28-17/h1-4,9-18,20-26H,5-6,19H2/t9?,10?,11-,12-,13+,14?,15?,16+,17-,18+/m1/s1
• InChIKey: VRQDYJFVDCOTOB-OQSVVHQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S,5S)-2-{[(2R,4S,5R)-2-(4-aminophenoxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,4S,5S)-2-{[(2R,4S,5R)-2-(4-aminophenoxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: 4-Aminophenyl 3-O-α-D-Glucopyranosyl-α-D-glucopyranoside; 4-Aminophenyl α-Nigeroside

Database IDs

• PubChem SID: 162254548
• PubChem CID: 71313335

CALCULATED PROPERTIES

• Acid pKa: 11.934278
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -3.2638679
• LogD (pH = 7.4): -3.199055
• 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

DETAILS

Toronto Research Chemicals - A625200

4-Aminophenyl α-Nigeroside is the aminophenyl analogue of the unfermentable sugar Nigerose.