(2S,6'R)-7-chloro-4-(13C,2H3)methoxy-2',6-dimethoxy-6'-methyl-3H-spiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione

• ChemBase ID: 169779
• Molecular Formular: C17H17ClO6
• Molecular Mass: 353.75893484
• Monoisotopic Mass: 353.07472078
• SMILES: c1c(c(c2c(c1O[13CH3])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[13CH3])cc(c1Cl)OC)C
• InChI: InChI=1S/C17H17ClO6/c1-8-5-9(19)6-12(23-4)17(8)16(20)13-10(21-2)7-11(22-3)14(18)15(13)24-17/h6-8H,5H2,1-4H3/t8-,17+/m1/s1/i2+1
• InChIKey: DDUHZTYCFQRHIY-YTYVCTAOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,6'R)-7-chloro-4-(^1^3C,^2H₃)methoxy-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-(^1^3C,^2H₃)methoxy-2',6-dimethoxy-6'-methylspiro[1-benzofuran-2,1'-cyclohexan]-2'-ene-3,4'-dione
• Synonyms: (1'S,6'R)-7-Chloro-2',6-dimethoxy-4-(methoxy-d3)-6'-methyl-spiro[benzofuran-2(3H),1'-[2]cyclohexene]-3,4'-dione; Amudane-13C,d3; Fulcin-13C,d3; Grisovin-13C,d3; Spirofulvin-13C,d3; Sporostatin-13C,d3; Xuanjing-13C,d3; Griseofulvin-13C,d3

Database IDs

• PubChem SID: 162263911
• PubChem CID: 71317161

CALCULATED PROPERTIES

• Acid pKa: 17.688671
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 2.1721375
• LogD (pH = 7.4): 2.1721375
• Log P: 2.1721375
• Molar Refractivity: 87.8459 cm^3
• Polarizability: 33.759495 Å^3
• Polar Surface Area: 71.06 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 204-211°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - G787502

Lalelled Griseofulvin (G787500). It is an antifungal drug. It is used both in animal and in humans, to treat rigworm infections of the skin and nails. It is derived from the mold Penicillium griseofulvum.

REFERENCES

• Oxford, et al.: Biochem. J., 33, 240 (1939)
• Townley, E.R., et al.: Anal. Profiles Drug Subs., 8, 219 (1939)