(1S,2R,4R,5R)-2-(2H3)methyl-1,7,7-trimethylbicyclo[2.2.1]heptane-2,5-diol

• ChemBase ID: 170858
• Molecular Formular: C11H20O2
• Molecular Mass: 184.2753
• Monoisotopic Mass: 184.14632988
• SMILES: C1[C@@]2([C@@](C[C@@H]([C@@H]1O)C2(C)C)(O)C)C
• Canonical SMILES: O[C@@H]1C[C@]2(C([C@H]1C[C@@]2(C)O)(C)C)C
• InChI: InChI=1S/C11H20O2/c1-9(2)7-5-11(4,13)10(9,3)6-8(7)12/h7-8,12-13H,5-6H2,1-4H3/t7-,8+,10-,11+/m0/s1
• InChIKey: YSYFMRPVURSGCW-GISOBZBCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,4R,5R)-2-(^2H₃)methyl-1,7,7-trimethylbicyclo[2.2.1]heptane-2,5-diol
• IUPAC Traditional name: (1S,2R,4R,5R)-2-(^2H₃)methyl-1,7,7-trimethylbicyclo[2.2.1]heptane-2,5-diol
• Synonyms: (1R,2R,4R,5R)-rel-1,2,7,7-Tetramethylbicyclo[2.2.1]heptane-2,5-diol-d3; 5-Hydroxy-2-MIB-d3; 5-Hydroxy-2-methyl Isoborneol-d3

Database IDs

• PubChem SID: 164226768
• PubChem CID: 71749162

CALCULATED PROPERTIES

• Acid pKa: 14.385195
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.96126974
• LogD (pH = 7.4): 0.96126974
• Log P: 0.96126974
• Molar Refractivity: 51.545 cm^3
• Polarizability: 20.77036 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H947942

A labelled metabolite of 2-Methylisoborneol (2-MIB). Many camphor-degrading bacteria which can transform 2-Methylisoborneol (2-MIB) have been identified. Rhodococcus wratislaviensis DLC-cam converts 2-MIB through 5-hydroxy-2-MIB to 5-keto-2-MIB.

REFERENCES

• Altschul, S., et al.: J. Mol. Biol., 215, 403 (1990)
• Raag, R., et al.: Biochemistry, 30, 2674 (1990)
• Eaton, R., et al.: J. Bacteriol., 183, 3689 (1990)