(11R,12S,13S,15R)-14-oxatetracyclo[8.5.0.02,7.013,15]pentadeca-1(10),2,4,6,8-pentaene-11,12-diol

• ChemBase ID: 167816
• Molecular Formular: C14H12O3
• Molecular Mass: 228.24328
• Monoisotopic Mass: 228.07864424
• SMILES: c1ccc2c(c1)ccc1c2[C@@H]2[C@H]([C@H]([C@@H]1O)O)O2
• Canonical SMILES: O[C@@H]1[C@@H]2O[C@@H]2c2c([C@H]1O)ccc1c2cccc1
• InChI: InChI=1S/C14H12O3/c15-11-9-6-5-7-3-1-2-4-8(7)10(9)13-14(17-13)12(11)16/h1-6,11-16H/t11-,12+,13-,14+/m1/s1
• InChIKey: YMUIEZKBBVSZNE-RQJABVFESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (11R,12S,13S,15R)-14-oxatetracyclo[8.5.0.0^2,^7.0^1^3,^1^5]pentadeca-1(10),2,4,6,8-pentaene-11,12-diol
• IUPAC Traditional name: (11R,12S,13S,15R)-14-oxatetracyclo[8.5.0.0^2,^7.0^1^3,^1^5]pentadeca-1(10),2,4,6,8-pentaene-11,12-diol
• Synonyms: (1aR,2R,3S,9cS)-rel-1a,2,3,9c-Tetrahydrophenanthro[3,4-b]oxirene-2,3-diol; (1aα,2β,3α,9cα)-1a,2,3,9c-Tetrahydrophenanthro[3,4-b]oxirene-2,3-diol; 1,2-Dihydroxy-3,4-epoxy-1,2,3,4-tetrahydrophenanthrene

Database IDs

• CAS Number: 67737-62-6
• PubChem SID: 162261949
• PubChem CID: 15928856

CALCULATED PROPERTIES

• Acid pKa: 12.815113
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.2770659
• LogD (pH = 7.4): 1.2770642
• Log P: 1.2770659
• Molar Refractivity: 61.9263 cm^3
• Polarizability: 25.660192 Å^3
• Polar Surface Area: 52.99 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 164°C (dec.)

DETAILS

Toronto Research Chemicals - D452810

A phenanthrene diol epoxide which shows a high mutagenicity and tumorigenicity effect in bacterial and mammalian cells.

REFERENCES

• Wood, A.W.; et al.: Cancer Res., 39, 4069 (1979)
• Adams, S.M., et al.: Molec. Pharmacol., 22, 459 (1979)
• Hradec, J., et al.: Carcinogenesis, 11, 1921 (1979)