(1R,4S,5R)-5-hydroxy-5-(2H3)methyl-4,7,7-trimethylbicyclo[2.2.1]heptan-2-one

• ChemBase ID: 172076
• Molecular Formular: C11H18O2
• Molecular Mass: 182.25942
• Monoisotopic Mass: 182.13067982
• SMILES: C1[C@@]2([C@@](C[C@@H](C1=O)C2(C)C)(O)C)C
• Canonical SMILES: O=C1C[C@]2(C([C@H]1C[C@@]2(C)O)(C)C)C
• InChI: InChI=1S/C11H18O2/c1-9(2)7-5-11(4,13)10(9,3)6-8(7)12/h7,13H,5-6H2,1-4H3/t7-,10-,11+/m0/s1
• InChIKey: WWCDYKJHABHQJH-BKDNQFJXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4S,5R)-5-hydroxy-5-(^2H₃)methyl-4,7,7-trimethylbicyclo[2.2.1]heptan-2-one
• IUPAC Traditional name: (1R,4S,5R)-5-hydroxy-5-(^2H₃)methyl-4,7,7-trimethylbicyclo[2.2.1]heptan-2-one
• Synonyms: (1R,4R,5R)-rel-5-Hydroxy-4,5,7,7-tetramethyl-bicyclo[2.2.1]heptan-2-one-d3; 5-Keto-2-methyl Isoborneol-d3

Database IDs

• PubChem SID: 164227986
• PubChem CID: 71749685

CALCULATED PROPERTIES

• Acid pKa: 14.517264
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.346784
• LogD (pH = 7.4): 1.346784
• Log P: 1.346784
• Molar Refractivity: 50.6198 cm^3
• Polarizability: 20.224808 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - K192502

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)