(2S,3S,5R,6S)-3,4,5-trihydroxy-6-{4-[(3E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenoxy}oxane-2-carboxylic acid

• ChemBase ID: 167362
• Molecular Formular: C24H28O8
• Molecular Mass: 444.47432
• Monoisotopic Mass: 444.17841786
• SMILES: [C@H]1(O[C@H]([C@H](C([C@@H]1O)O)O)C(=O)O)Oc1ccc(cc1)/C(=C(/c1ccc(cc1)O)\CC)/CC
• Canonical SMILES: CC/C(=C(\c1ccc(cc1)O)/CC)/c1ccc(cc1)O[C@@H]1O[C@@H](C(=O)O)[C@H](C([C@@H]1O)O)O
• InChI: InChI=1S/C24H28O8/c1-3-17(13-5-9-15(25)10-6-13)18(4-2)14-7-11-16(12-8-14)31-24-21(28)19(26)20(27)22(32-24)23(29)30/h5-12,19-22,24-28H,3-4H2,1-2H3,(H,29,30)/b18-17+/t19?,20-,21+,22-,24+/m0/s1
• InChIKey: LJMPVHCKUXKZAV-KOFPWNEFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,5R,6S)-3,4,5-trihydroxy-6-{4-[(3E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenoxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,5R,6S)-3,4,5-trihydroxy-6-{4-[(3E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenoxy}oxane-2-carboxylic acid
• Synonyms: 4-[(1E)-1-Ethyl-2-(4-hydroxyphenyl)-1-buten-1-yl]phenyl β-D-Glucopyranosiduronic Acid; Diethylstilbestrol Monoglucuronide; Stilbestrol Monoglucuronide; Diethyl Stilbestrol β-D-Glucuronide

Database IDs

• CAS Number: 2408-40-4
• PubChem SID: 162261495
• PubChem CID: 71316059

CALCULATED PROPERTIES

• Acid pKa: 3.24885
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 1.014758
• LogD (pH = 7.4): -0.19436847
• Log P: 3.2460892
• Molar Refractivity: 115.2524 cm^3
• Polarizability: 45.585033 Å^3
• Polar Surface Area: 136.68 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 173-175°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D445020

A metabolite of Fosfestrol.

REFERENCES

• Vanluchene, E., et al.: J. Steroid Biochem., 16, 701 (1982)
• Fodey, T., et al.: Food Agric. Immunol., 8, 157 (1982)