5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylic acid

• ChemBase ID: 175938
• Molecular Formular: C14H24N2O4
• Molecular Mass: 284.35136
• Monoisotopic Mass: 284.17360726
• SMILES: C1(C(CC(=CC1OC(CC)CC)C(=O)O)N)NC(=O)C
• Canonical SMILES: CCC(OC1C=C(CC(C1NC(=O)C)N)C(=O)O)CC
• InChI: InChI=1S/C14H24N2O4/c1-4-10(5-2)20-12-7-9(14(18)19)6-11(15)13(12)16-8(3)17/h7,10-13H,4-6,15H2,1-3H3,(H,16,17)(H,18,19)
• InChIKey: NENPYTRHICXVCS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylic acid
• IUPAC Traditional name: 5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylic acid
• Synonyms: (3R,4R,5S)-4-(Acetylamino)-5-amino-3-(1-ethylpropoxy)-1-cyclohexence-1-carboxylic Acid; Oseltamivir Carboxylic Acid; GS 4071; Ro 64-0802; Oseltamivir Acid

Database IDs

• CAS Number: 187227-45-8
• PubChem SID: 164231848
• PubChem CID: 4631786

CALCULATED PROPERTIES

• Acid pKa: 4.377217
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.8612062
• LogD (pH = 7.4): -1.8401768
• Log P: -1.8378457
• Molar Refractivity: 74.6857 cm^3
• Polarizability: 29.524708 Å^3
• Polar Surface Area: 101.65 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: water
• Apperance: White Solid
• Melting Point: 183-185°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - O700980

Oseltamivir Acid is a metabolite of Oseltamivir (O701000).

REFERENCES

• Oliyai, R., et al.: Pharm. Res., 15, 1300 (1998)
• Kim, C.U., et al.: Med. Chem. Res., 8, 392 (1998)
• Hayden, F.G., et al.: N. Engl. J. Med., 341, 1336 (1998)
• Treanor, J.J., et al.: J. Am. Med. Assoc., 283, 1016 (2000)