(3S,3aS,9aS,9bS)-3,6,9-trimethyl-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

• ChemBase ID: 179746
• Molecular Formular: C15H18O3
• Molecular Mass: 246.30162
• Monoisotopic Mass: 246.12559444
• SMILES: [C@@H]12[C@H]3OC(=O)[C@H]([C@@H]3CCC(=C1C(=O)C=C2C)C)C
• Canonical SMILES: C[C@@H]1C(=O)O[C@H]2[C@H]1CCC(=C1[C@@H]2C(=CC1=O)C)C
• InChI: InChI=1S/C15H18O3/c1-7-4-5-10-9(3)15(17)18-14(10)13-8(2)6-11(16)12(7)13/h6,9-10,13-14H,4-5H2,1-3H3/t9-,10-,13-,14-/m0/s1
• InChIKey: BJPSSVHNEGMBDQ-NUZBWSBOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,3aS,9aS,9bS)-3,6,9-trimethyl-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione
• IUPAC Traditional name: (3S,3aS,9aS,9bS)-3,6,9-trimethyl-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione
• Synonyms: Desacetoxymatricarin; Leukodin; Leucomisin; Axillin; Deacetoxymatricarin

Database IDs

• CAS Number: 17946-87-1
• PubChem SID: 164235656
• PubChem CID: 167683

CALCULATED PROPERTIES

• Acid pKa: 15.413396
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.4665372
• LogD (pH = 7.4): 2.4665372
• Log P: 2.4665372
• Molar Refractivity: 68.7163 cm^3
• Polarizability: 26.52878 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Effects NF-kB (Nuclear Factor-kB)

Product Information

• Biological Source: Constit. of Artemisia spp., Achillea spp., and Stevia pilosa
• Application(s): Cytitoxic; Hepatotropic

REFERENCES

• Rybalko, K.S., Zh. Obshch. Khim., 1963, 33, 2734; J. Gen. Chem. USSR (Engl. Transl.), 1963, 33, 2663, (Leucomisin)
• White, E.H.S. et al., Tetrahedron, 1969, 25, 2099, (synth)
• Marx, J.N. et al., Tetrahedron, 1969, 25, 2117, (isol)
• Shafizadeh, F. et al., J.O.C., 1972, 37, 3168, (isol)
• Bohlmann, F. et al., Tet. Lett., 1972, 621, (isol)
• Gonzlez, A.G. et al., An. Quim., Ser. C, 1976, 72C, 695, (isol)
• Martinez, V.M. et al., J. Nat. Prod., 1988, 51, 221, (pmr, cmr)
• Marco, J.A. et al., J. Nat. Prod., 1989, 52, 547, (cryst struct, pmr, cmr)
• Banerjee, A.K. et al., Tetrahedron, 1993, 49, 4761, (synth, rev)
• Ando, M. et al., J. Nat. Prod., 1994, 57, 433, (synth)
• Brengio, S.D. et al., J. Parasitol., 2000, 86, 407-412, (activity)