(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-methyl-2-(propan-2-yl)(1,2,6,6-2H4)cyclohexyl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 172654
• Molecular Formular: C16H28O7
• Molecular Mass: 332.38932
• Monoisotopic Mass: 332.18350324
• SMILES: C1C(CCC(C1O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O)C(C)C)C
• Canonical SMILES: CC1CCC(C(C1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C(C)C
• InChI: InChI=1S/C16H28O7/c1-7(2)9-5-4-8(3)6-10(9)22-16-13(19)11(17)12(18)14(23-16)15(20)21/h7-14,16-19H,4-6H2,1-3H3,(H,20,21)/t8?,9?,10?,11-,12-,13+,14-,16+/m0/s1
• InChIKey: CLJGMBYGTHRUNF-SHLVDPONSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[5-methyl-2-(propan-2-yl)(1,2,6,6-^2H₄)cyclohexyl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-isopropyl-5-methyl(1,2,6,6-^2H₄)cyclohexyl]oxy}oxane-2-carboxylic acid
• Synonyms: 5-Methyl-2-(1-methylethyl)cyclohexyl-d4 β-D-Glucopyranosiduronic Acid; p-Menth-3-yl-d4 Glucosiduronic Acid; Menthol-d4 β-D-Glucuronide (Mixture of Diasteromers)

Database IDs

• PubChem SID: 164228564
• PubChem CID: 71749956

CALCULATED PROPERTIES

• Acid pKa: 3.9110594
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -0.38132527
• LogD (pH = 7.4): -1.9941368
• Log P: 1.2137121
• Molar Refractivity: 79.726 cm^3
• Polarizability: 32.641827 Å^3
• Polar Surface Area: 116.45 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M218907

Labelled DL-Menthol β-D-Glucuronide. DL-Menthol β-D-Glucuronide is a metabolite of DL-Methanol.

REFERENCES

• Eccles, R., et al.: J. Pharm. Pharmacol., 46, 618 (1994)
• Feng, S., et al.: Toxicol. Lett., 173, 101 (1994)
• Dempsey, D., et al.: Clin. Pharmacol. Ther., 76, 64 (1994)