(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-[4-hydroxy-3,5-bis(propan-2-yl)phenoxy]oxane-2-carboxylic acid

• ChemBase ID: 171091
• Molecular Formular: C18H26O8
• Molecular Mass: 370.39424
• Monoisotopic Mass: 370.16276779
• SMILES: Oc1c(cc(cc1C(C)C)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O)C(C)C
• Canonical SMILES: OC(=O)[C@H]1O[C@H](Oc2cc(C(C)C)c(c(c2)C(C)C)O)[C@@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C18H26O8/c1-7(2)10-5-9(6-11(8(3)4)12(10)19)25-18-15(22)13(20)14(21)16(26-18)17(23)24/h5-8,13-16,18-22H,1-4H3,(H,23,24)/t13-,14-,15+,16-,18+/m1/s1
• InChIKey: UXCRGVWMLWGVRH-QFXBJFAPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-[4-hydroxy-3,5-bis(propan-2-yl)phenoxy]oxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(4-hydroxy-3,5-diisopropylphenoxy)oxane-2-carboxylic acid
• Synonyms: 4-Hydroxy-3,5-bis(1-methylethyl)phenyl β-D-Glucopyranosiduronic Acid; 4-Hydroxy Propofol 4-O-β-D-Glucuronide

Database IDs

• CAS Number: 115005-78-2
• PubChem SID: 164227001
• PubChem CID: 10384525

CALCULATED PROPERTIES

• Acid pKa: 3.0452707
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -0.5128078
• LogD (pH = 7.4): -1.5607982
• Log P: 1.90834
• Molar Refractivity: 90.4132 cm^3
• Polarizability: 36.03615 Å^3
• Polar Surface Area: 136.68 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 116-118°C

Safety Information

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

DETAILS

Toronto Research Chemicals - H950780

A metabolite of Propofol. Anesthetic (intravenous).

REFERENCES

• Davies, M., et al.: Biochem. J., 257, 603 (1989)
• Eriksson, O., et al.: Biochem. Pharmacol., 44, 391 (1989)
• Bryson, H., et al.: Drugs, 50, 513, (1989)
• Raoof, A., et al.: Eur. J. Clin. Pharmacol., 50, 91 (1996)