methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-(4-aminophenoxy)oxane-2-carboxylate

• ChemBase ID: 160429
• Molecular Formular: C19H23NO10
• Molecular Mass: 425.38662
• Monoisotopic Mass: 425.13219594
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1C(=O)OC)Oc1ccc(cc1)N)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](Oc2ccc(cc2)N)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C19H23NO10/c1-9(21)26-14-15(27-10(2)22)17(28-11(3)23)19(30-16(14)18(24)25-4)29-13-7-5-12(20)6-8-13/h5-8,14-17,19H,20H2,1-4H3/t14-,15-,16-,17+,19+/m0/s1
• InChIKey: IGHOHCWHGMRAMB-YTGMWSOZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-(4-aminophenoxy)oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-(4-aminophenoxy)oxane-2-carboxylate
• Synonyms: p-Aminophenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate; 4-Aminophenyl 2,3,4-Tri-O-acetyl-β-D-glucuronide Methyl Ester

Database IDs

• CAS Number: 25218-22-8
• PubChem SID: 162254564
• PubChem CID: 71313340

CALCULATED PROPERTIES

• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 0.3068865
• LogD (pH = 7.4): 0.36148825
• Log P: 0.36223128
• Molar Refractivity: 96.9747 cm^3
• Polarizability: 39.38524 Å^3
• Polar Surface Area: 149.68 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Light Brown Solid
• Melting Point: 151-153°C

Safety Information

• Storage Condition: -20°C Freezer

REFERENCES

• Iino, N., et al.: Chem. Pharm. Bull., 40, 1852 (1992)