ethyl 4-{[(2R,4R,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]amino}benzoate

• ChemBase ID: 161250
• Molecular Formular: C15H21NO7
• Molecular Mass: 327.32974
• Monoisotopic Mass: 327.13180202
• SMILES: c1(ccc(cc1)C(=O)OCC)N[C@]1(C([C@H]([C@H](O1)CO)O)O)CO
• Canonical SMILES: CCOC(=O)c1ccc(cc1)N[C@]1(CO)O[C@@H]([C@@H](C1O)O)CO
• InChI: InChI=1S/C15H21NO7/c1-2-22-14(21)9-3-5-10(6-4-9)16-15(8-18)13(20)12(19)11(7-17)23-15/h3-6,11-13,16-20H,2,7-8H2,1H3/t11-,12+,13?,15-/m1/s1
• InChIKey: QPYPPHVWJURKPP-RLCAUIQDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 4-{[(2R,4R,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]amino}benzoate
• IUPAC Traditional name: ethyl 4-{[(2R,4R,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]amino}benzoate
• Synonyms: 4-(D-fructofuranosylamino)benzoic Acid Ethyl Ester; Benzocaine N-D-Fructoside

Database IDs

• CAS Number: 78306-17-9
• PubChem SID: 162255385
• PubChem CID: 71313693

CALCULATED PROPERTIES

• Acid pKa: 10.219655
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -0.43312126
• LogD (pH = 7.4): -0.43373817
• Log P: -0.4331134
• Molar Refractivity: 81.1252 cm^3
• Polarizability: 31.372597 Å^3
• Polar Surface Area: 128.48 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B202980

The N-Fructoside of Benzocaine (B202970).