2-hydroxy-N-{2-[(8S)-1H,2H,6H,7H,8H-indeno[5,4-b]furan-8-yl]ethyl}(3,3,3-2H3)propanamide

• ChemBase ID: 177344
• Molecular Formular: C16H21NO3
• Molecular Mass: 275.34284
• Monoisotopic Mass: 275.15214354
• SMILES: c1c2c(c3c(c1)CC[C@H]3CCNC(=O)C(O)C)CCO2
• Canonical SMILES: O=C(C(O)C)NCC[C@@H]1CCc2c1c1CCOc1cc2
• InChI: InChI=1S/C16H21NO3/c1-10(18)16(19)17-8-6-12-3-2-11-4-5-14-13(15(11)12)7-9-20-14/h4-5,10,12,18H,2-3,6-9H2,1H3,(H,17,19)/t10?,12-/m0/s1
• InChIKey: FGFNIJYHXMJYJN-KFJBMODSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-N-{2-[(8S)-1H,2H,6H,7H,8H-indeno[5,4-b]furan-8-yl]ethyl}(3,3,3-^2H₃)propanamide
• IUPAC Traditional name: 2-hydroxy-N-{2-[(8S)-1H,2H,6H,7H,8H-indeno[5,4-b]furan-8-yl]ethyl}(3,3,3-^2H₃)propanamide
• Synonyms: 2-Hydroxy-N-[2-[(8S)-1,6,7,8-tetrahydro-2H-cyclopenta[e]benzofuran-8-yl]ethyl]propanamide-d3; Ramelteon Metabolite M-II-d3 (mixture of R and S at the hydroxy position)

Database IDs

• PubChem SID: 164233254
• PubChem CID: 71751961

CALCULATED PROPERTIES

• Acid pKa: 13.4761305
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.6215388
• LogD (pH = 7.4): 1.6215384
• Log P: 1.6215388
• Molar Refractivity: 77.0877 cm^3
• Polarizability: 29.636501 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 94-96°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - R110062

The major metabolite of Ramelteon in serum (M-II).

REFERENCES

• Karim, A., et al.: J. Clin. Pharmacol., 44, 1210 (2004)
• Prescott, E., et al.: Drug Metab. Rev., 36, 203 (2004)
• Kato, K., et al.: Neuropharmacology, 48, 301 (2004)
• Karim, A., et al.: J. Clin. Pharmacol., 46, 140 (2004)