(2S,6'R)-7-chloro-2'-hydroxy-4,6-dimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione

• ChemBase ID: 165779
• Molecular Formular: C16H15ClO6
• Molecular Mass: 338.7397
• Monoisotopic Mass: 338.05571588
• SMILES: c1c(c(c2c(c1OC)C(=O)[C@]1(O2)[C@@H](CC(=O)C=C1O)C)Cl)OC
• Canonical SMILES: COc1cc(OC)c(c2c1C(=O)[C@]1(O2)[C@H](C)CC(=O)C=C1O)Cl
• InChI: InChI=1S/C16H15ClO6/c1-7-4-8(18)5-11(19)16(7)15(20)12-9(21-2)6-10(22-3)13(17)14(12)23-16/h5-7,19H,4H2,1-3H3/t7-,16+/m1/s1
• InChIKey: KUTVEHNZHKAAAO-QZTNRIJFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,6'R)-7-chloro-2'-hydroxy-4,6-dimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione
• IUPAC Traditional name: (2S,6'R)-7-chloro-2'-hydroxy-4,6-dimethoxy-6'-methylspiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione
• Synonyms: (1'S,6'R)-7-Chloro-4'-hydroxy-4,6-dimethoxy-6'-methyl-spiro[benzofuran-2(3H),1'-[3]cyclohexene]-2',3-dione; 4'-O-Demethyl Griseofulvin

Database IDs

• CAS Number: 1158186-19-6
• PubChem SID: 162259912
• PubChem CID: 15086460

CALCULATED PROPERTIES

• Acid pKa: 4.2226887
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 0.76207334
• LogD (pH = 7.4): -0.95858103
• Log P: 2.05931
• Molar Refractivity: 83.0947 cm^3
• Polarizability: 31.866516 Å^3
• Polar Surface Area: 82.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Water
• Apperance: White Solid

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D231070

Griseofulvin (G787500) derivative.

REFERENCES

• Ronnest, M. et al.: J. Med. Chem. 52, 3342 (2009)