(2S,6'R)-7-chloro-4,6-dimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexane]-2',3,4'-trione

• ChemBase ID: 169778
• 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)CC1=O)C)Cl)OC
• Canonical SMILES: COc1cc(OC)c(c2c1C(=O)[C@]1(O2)[C@H](C)CC(=O)CC1=O)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/h6-7H,4-5H2,1-3H3/t7-,16+/m1/s1
• InChIKey: YIQRSAKVWZVLDN-QZTNRIJFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,6'R)-7-chloro-4,6-dimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexane]-2',3,4'-trione
• IUPAC Traditional name: (2S,6'R)-7-chloro-4,6-dimethoxy-6'-methylspiro[1-benzofuran-2,1'-cyclohexane]-2',3,4'-trione
• Synonyms: (1'S,6'R)-7-Chloro-4,6-dimethoxy-6'-methyl-,Spiro[benzofuran-2(3H),1'-cyclohexane]-2',3,4'-trione; trans-7-Chloro-4,6-dimethoxy-6'-methylspiro[benzofuran-2(3H),1'-cyclohexane]-2',3,4'-trione; (+/-)-Griseofulvic Acid; Griseofulvic Acid

Database IDs

• CAS Number: 469-54-5
• PubChem SID: 162263910
• PubChem CID: 71317160

CALCULATED PROPERTIES

• Acid pKa: 8.030868
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 2.5757082
• LogD (pH = 7.4): 2.4857516
• Log P: 2.5769844
• Molar Refractivity: 80.8541 cm^3
• Polarizability: 31.58115 Å^3
• Polar Surface Area: 78.9 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 260-262°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - G787490

A newly 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)