(3S,3aR,4S,9aS,9bR)-3,6,9-trimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

• ChemBase ID: 179766
• Molecular Formular: C17H20O5
• Molecular Mass: 304.3377
• Monoisotopic Mass: 304.13107374
• SMILES: [C@@H]12[C@H]3OC(=O)[C@H]([C@@H]3[C@H](CC(=C1C(=O)C=C2C)C)OC(=O)C)C
• Canonical SMILES: CC(=O)O[C@H]1CC(=C2[C@@H]([C@@H]3[C@@H]1[C@H](C)C(=O)O3)C(=CC2=O)C)C
• InChI: InChI=1S/C17H20O5/c1-7-5-11(19)13-8(2)6-12(21-10(4)18)15-9(3)17(20)22-16(15)14(7)13/h5,9,12,14-16H,6H2,1-4H3/t9-,12-,14-,15+,16+/m0/s1
• InChIKey: QONYNSMAVSRIRD-UPQAZBFISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,3aR,4S,9aS,9bR)-3,6,9-trimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate
• IUPAC Traditional name: (3S,3aR,4S,9aS,9bR)-3,6,9-trimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate
• Synonyms: Artilesin A; Matricarin

Database IDs

• CAS Number: 5989-43-5
• PubChem SID: 164235676
• PubChem CID: 3083923

CALCULATED PROPERTIES

• Acid pKa: 15.018363
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.5625007
• LogD (pH = 7.4): 1.5625007
• Log P: 1.5625007
• Molar Refractivity: 79.4385 cm^3
• Polarizability: 31.019188 Å^3
• Polar Surface Area: 69.67 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Inhibitor of metabotropic glutamate receptors

Product Information

• Biological Source: Constit. of Achillea lanulosa
• Application(s): Cytostatic

REFERENCES

• Herz, W. et al., J.A.C.S., 1961, 83, 1139, (isol)
• White, E.H. et al., Tet. Lett., 1969, 25, 2099, (struct)
• Bachelor, F.W. et al., Can. J. Chem., 1972, 50, 333, (struct)
• Zakharov, P.I. et al., Khim. Prir. Soedin., 1977, 13, 344; Chem. Nat. Compd. (Engl. Transl.), 1977, 13, 293, (ms)
• Collado, I.G. et al., J.C.S. Perkin 1, 1987, 1641-1644, (struct)
• Martinez V'., M. et al., J. Nat. Prod., 1988, 51, 221-228, (pmr, cmr)
• Campos, V. et al., Acta Cryst. C, 1989, 45, 678, (cryst struct)
• Turdybekov, K.M. et al., Khim. Prir. Soedin., 1989, 788; Chem. Nat. Compd. (Engl. Transl.), 1989, 25, 699, (cryst struct)
• Rychlewzka, U. et al., Acta Cryst. C, 1991, 47, 1872, (cryst struct)
• Okunade, A.L. et al., Phytochemistry, 1994, 35, 191-194, (tigloyl)