1-(2-{4-[(1R,2S)-6-hydroxy-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl]phenoxy}ethyl)pyrrolidin-2-one

• ChemBase ID: 172231
• Molecular Formular: C28H29NO3
• Molecular Mass: 427.53476
• Monoisotopic Mass: 427.21474379
• SMILES: c1c(cc2c(c1)[C@H]([C@H](CC2)c1ccccc1)c1ccc(cc1)OCCN1C(=O)CCC1)O
• Canonical SMILES: Oc1ccc2c(c1)CC[C@@H]([C@@H]2c1ccc(cc1)OCCN1CCCC1=O)c1ccccc1
• InChI: InChI=1S/C28H29NO3/c30-23-11-15-26-22(19-23)10-14-25(20-5-2-1-3-6-20)28(26)21-8-12-24(13-9-21)32-18-17-29-16-4-7-27(29)31/h1-3,5-6,8-9,11-13,15,19,25,28,30H,4,7,10,14,16-18H2/t25-,28+/m1/s1
• InChIKey: YBFAWBLHDMBREC-NAKRPHOHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2-{4-[(1R,2S)-6-hydroxy-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl]phenoxy}ethyl)pyrrolidin-2-one
• IUPAC Traditional name: 1-(2-{4-[(1R,2S)-6-hydroxy-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl]phenoxy}ethyl)pyrrolidin-2-one
• Synonyms: 1-[2-[4-[(1R,2S)-1,2,3,4-Tetrahydro-6-hydroxy-2-phenyl-1-naphthalenyl]phenoxy]ethyl]-2-pyrrolidinone; Lasofoxifene 2-Oxide

Database IDs

• CAS Number: 366017-88-1
• PubChem SID: 164228141
• PubChem CID: 10296135

CALCULATED PROPERTIES

• Acid pKa: 10.183873
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 5.2784424
• LogD (pH = 7.4): 5.2777414
• Log P: 5.2784514
• Molar Refractivity: 126.4571 cm^3
• Polarizability: 48.73894 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - L176515

A metabolite of Lasofoxifene (L176500) in humans, (oxidation on the pyrrolidine moiety).

REFERENCES

• Monks, T., et al.: Toxicol. Appl. Pharmacol., 112, 2 (1992)
• Luisetto, G., et al.: Bone Miner., 22, 9 (1992)
• Rosati, R., et al.: J. Med. Chem., 41, 2928 (1992)
• Mattiuz, E., et al.: Drug Metab. Dispos., 31, 88 (1992)
• Kamel, A., et al.: Curr Drug. Metab.