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

• ChemBase ID: 165780
• Molecular Formular: C16H15ClO6
• Molecular Mass: 338.7397
• Monoisotopic Mass: 338.05571588
• SMILES: c1c(c(c2c(c1O)C(=O)[C@]1(O2)[C@@H](CC(=O)C=C1OC)C)Cl)OC
• Canonical SMILES: COC1=CC(=O)C[C@H]([C@@]21Oc1c(C2=O)c(O)cc(c1Cl)OC)C
• InChI: InChI=1S/C16H15ClO6/c1-7-4-8(18)5-11(22-3)16(7)15(20)12-9(19)6-10(21-2)13(17)14(12)23-16/h5-7,19H,4H2,1-3H3/t7-,16+/m1/s1
• InChIKey: KTICLSBYPHKDMM-QZTNRIJFSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 5128-41-6
• PubChem SID: 162259913
• PubChem CID: 44565921

CALCULATED PROPERTIES

• Acid pKa: 8.085656
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.6751268
• LogD (pH = 7.4): 2.5955563
• Log P: 2.6762433
• Molar Refractivity: 83.3636 cm^3
• Polarizability: 31.867096 Å^3
• Polar Surface Area: 82.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D231075

A metabolite of Griseofulvin (G787500).

REFERENCES

• Oda, T., et al.: J. Antibiot., 59, 114 (2006)
• Rebacz, B., et al.: Cancer Res., 67, 6342 (2006)
• Uen, Y., et al.: J. Cell Biochem., 101, 1165 (2006)