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

• ChemBase ID: 172651
• Molecular Formular: C16H28O7
• Molecular Mass: 332.38932
• Monoisotopic Mass: 332.18350324
• SMILES: C1[C@@H](CC[C@H]([C@@H]1O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O)C(C)C)C
• Canonical SMILES: C[C@@H]1CC[C@H]([C@@H](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-/m1/s1
• InChIKey: CLJGMBYGTHRUNF-PJQJKGEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy}oxane-2-carboxylic acid
• Synonyms: (1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexylβ-D-Glucopyranosiduronic Αcid; l-Menthyl β-D-Glucopyranosiduronic Acid; [1R-(1α,2β,5β)]-5-Μethyl-2-(1-methylethyl)cyclohexyl β-D-Glucopyranosiduronic Acid; Menthol Glucuronide; l-Menthol Glucuronide; l-Menthyl Glucuronide; (1R,2S,5R)-(-)-Menthol β-D-Glucuronide

Database IDs

• CAS Number: 79466-08-3
• PubChem SID: 164228561
• PubChem CID: 71749954

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 - M218880

(1R,2S,5R)-(-)-Menthol β-D-Glucuronide is a metabolite of L-(-)-Menthol (M218875), the natural form of 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)