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

• ChemBase ID: 172652
• 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+/m0/s1
• InChIKey: CLJGMBYGTHRUNF-YJQUKTSOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,2R,5S)-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-{[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyl]oxy}oxane-2-carboxylic acid
• Synonyms: [1S-(1α,2β,5α)]-5-Methyl-2-(1-methylethyl)cyclohexyl β-D-Glucopyranosiduronic Acid; (1S,2R,5S)-(+)-Menthol β-D-Glucuronide

Database IDs

• CAS Number: 114127-73-0
• PubChem SID: 164228562
• PubChem CID: 71749955

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 - M218890

(1S,2R,5S)-(+)-Menthol β-D-Glucuronide is a metabolite of D-(+)-Menthol (M218885).

REFERENCES

• Sasaki, Y., et al.: Agric. Biol. Chem., 52, 207 (1988)