(9R,10S)-9,10-dihydrophenanthrene-9,10-diol

• ChemBase ID: 167810
• Molecular Formular: C14H12O2
• Molecular Mass: 212.24388
• Monoisotopic Mass: 212.08372962
• SMILES: c1ccc2c(c1)c1c([C@H]([C@H]2O)O)cccc1
• Canonical SMILES: O[C@@H]1[C@H](O)c2ccccc2c2c1cccc2
• InChI: InChI=1S/C14H12O2/c15-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)14(13)16/h1-8,13-16H/t13-,14+
• InChIKey: MFXNBQWUTDDOKE-OKILXGFUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (9R,10S)-9,10-dihydrophenanthrene-9,10-diol
• IUPAC Traditional name: (9R,10S)-9,10-dihydrophenanthrene-9,10-diol
• Synonyms: (9R,10S)-rel-9,10-Dihydro-9,10-dihydroxyphenanthrene; 9,10-Dihydrophenanthrene-cis-9,10-diol; Phenanthrene cis-9,10-Hihydrodiol; cis-9,10-Dihydro-9,10-phenanthrenediol; cis-9,10-Dihydroxy-9,10-dihydrophenanthrene

Database IDs

• CAS Number: 2510-71-6
• PubChem SID: 162261943
• PubChem CID: 818822

CALCULATED PROPERTIES

• Acid pKa: 13.135077
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.0337808
• LogD (pH = 7.4): 2.03378
• Log P: 2.0337808
• Molar Refractivity: 62.1974 cm^3
• Polarizability: 25.506145 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D452750

A dihydroxy metabolite of Phenanthrene with cis conformation. Produced via degradation by phenoloxidases and dioxygenases of Polyporus sp. S133.

REFERENCES

• Hadibarata, T. et al.: J. Microb. Biotech., 21, 299 (2011)
• Pathak, H. et al.: Bioremed., 12, 119 (2011)
• Moody, J.D. et al.: App. Env. Microbiol., 67, 1476 (2011)