(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(5R,6S)-6-phenyl-5-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 172229
• Molecular Formular: C34H39NO8
• Molecular Mass: 589.67536
• Monoisotopic Mass: 589.26756721
• SMILES: c1c(cc2c(c1)[C@H]([C@H](CC2)c1ccccc1)c1ccc(cc1)OCCN1CCCC1)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Oc2ccc3c(c2)CC[C@@H]([C@@H]3c2ccc(cc2)OCCN2CCCC2)c2ccccc2)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C34H39NO8/c36-29-30(37)32(33(39)40)43-34(31(29)38)42-25-13-15-27-23(20-25)10-14-26(21-6-2-1-3-7-21)28(27)22-8-11-24(12-9-22)41-19-18-35-16-4-5-17-35/h1-3,6-9,11-13,15,20,26,28-32,34,36-38H,4-5,10,14,16-19H2,(H,39,40)/t26-,28+,29+,30+,31-,32+,34-/m1/s1
• InChIKey: WBWCSRRUQKSEDJ-WIYFCYHXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(5R,6S)-6-phenyl-5-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(5R,6S)-6-phenyl-5-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}-5,6,7,8-tetrahydronaphthalen-2-yl]oxy}oxane-2-carboxylic acid
• Synonyms: (5R,6S)-5,6,7,8-Tetrahydro-6-phenyl-5-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-2-naphthalen β-D-Glucopyranosiduronic Acid; Lasofoxifene β-D-Glucuronide

Database IDs

• CAS Number: 1048953-95-2
• PubChem SID: 164228139
• PubChem CID: 71749751

CALCULATED PROPERTIES

• Acid pKa: 2.982654
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 1.5507103
• LogD (pH = 7.4): 1.5429866
• Log P: 1.551212
• Molar Refractivity: 158.8434 cm^3
• Polarizability: 62.51918 Å^3
• Polar Surface Area: 128.92 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - L176510

A metabolite of Lasofoxifene (L176500) in humans.

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.