(1S,2S,3R,4S)-2-(2H3)methyl-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol

• ChemBase ID: 170856
• Molecular Formular: C11H20O2
• Molecular Mass: 184.2753
• Monoisotopic Mass: 184.14632988
• SMILES: C1[C@@]2([C@@]([C@@H]([C@@H](C1)C2(C)C)O)(O)C)C
• Canonical SMILES: O[C@@H]1[C@H]2CC[C@]([C@]1(C)O)(C2(C)C)C
• InChI: InChI=1S/C11H20O2/c1-9(2)7-5-6-10(9,3)11(4,13)8(7)12/h7-8,12-13H,5-6H2,1-4H3/t7-,8-,10+,11-/m1/s1
• InChIKey: GROZVIRKNWHGSN-DEKFOEGESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S)-2-(^2H₃)methyl-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol
• IUPAC Traditional name: (1S,2S,3R,4S)-2-(^2H₃)methyl-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diol
• Synonyms: (1R,2S,3R,4S)-rel-1,2,7,7-Tetramethyl-Bicyclo[2.2.1]heptane-2,3-diol-d3; 3-Hydroxy-2-MIB-d3; 3-Hydroxy-2-methyl Isoborneol-d3

Database IDs

• PubChem SID: 164226766
• PubChem CID: 71749160

CALCULATED PROPERTIES

• Acid pKa: 13.399665
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.2730846
• LogD (pH = 7.4): 1.2730843
• Log P: 1.2730846
• Molar Refractivity: 51.237 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 - H947937

A metabolite of 2-Methylisoborneol (2-MIB). Many camphor-degrading bacteria which can transform 2-Methylisoborneol (2-MIB) have been identified. Rhodococcus ruber T1, which metabolizes camphor through 6-hydroxycamphor, converts 2-MIB to 3-hydroxy-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)