ethyl (4R,5S)-5-amino-2-azido-4-acetamido-3-(pentan-3-yloxy)cyclohexane-1-carboxylate

• ChemBase ID: 161014
• Molecular Formular: C16H29N5O4
• Molecular Mass: 355.43256
• Monoisotopic Mass: 355.22195443
• SMILES: [C@H]1([C@@H](CC(C(C1OC(CC)CC)N=[N+]=[N-])C(=O)OCC)N)NC(=O)C
• Canonical SMILES: CCOC(=O)C1C[C@@H](N)[C@H](C(C1N=[N+]=[N-])OC(CC)CC)NC(=O)C
• InChI: InChI=1S/C16H29N5O4/c1-5-10(6-2)25-15-13(20-21-18)11(16(23)24-7-3)8-12(17)14(15)19-9(4)22/h10-15H,5-8,17H2,1-4H3,(H,19,22)/t11?,12-,13?,14+,15?/m0/s1
• InChIKey: GSFIWDGFHNAUFU-VNECMYLUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (4R,5S)-5-amino-2-azido-4-acetamido-3-(pentan-3-yloxy)cyclohexane-1-carboxylate
• IUPAC Traditional name: ethyl (4R,5S)-5-amino-2-azido-4-acetamido-3-(pentan-3-yloxy)cyclohexane-1-carboxylate
• Synonyms: (3S,4R,5S)-4-Amino-5-amino-2-azido-3-(1-ethylpropoxy)cyclohexane-1-carboxylic Acid Ethyl Ester; 2-Azido-1,2-dihydro Oseltamivir (Mixture of Diastereomers)

Database IDs

• PubChem SID: 162255149
• PubChem CID: 71313583

CALCULATED PROPERTIES

• Acid pKa: 13.908665
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -2.262499
• LogD (pH = 7.4): -1.2185706
• Log P: 0.82431835
• Molar Refractivity: 90.9815 cm^3
• Polarizability: 36.00655 Å^3
• Polar Surface Area: 120.08 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A844600

An impurity of the antiviral drug Oseltamivir (O700100).