1,2,7,7-tetramethylbicyclo[2.2.1]heptane-2,5-diol

• ChemBase ID: 170857
• Molecular Formular: C11H20O2
• Molecular Mass: 184.2753
• Monoisotopic Mass: 184.14632988
• SMILES: C1C2(C(CC(C1O)C2(C)C)(O)C)C
• Canonical SMILES: OC1CC2(C(C1CC2(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
• InChIKey: YSYFMRPVURSGCW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,2,7,7-tetramethylbicyclo[2.2.1]heptane-2,5-diol
• IUPAC Traditional name: 1,2,7,7-tetramethylbicyclo[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; 5-Hydroxy-2-MIB; 5-Hydroxy-2-methyl Isoborneol

Database IDs

• CAS Number: 604767-98-8
• PubChem SID: 164226767
• PubChem CID: 71749161

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 - H947940

A 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)