(3aS,11aR)-6,10-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one

• ChemBase ID: 126716
• Molecular Formular: C15H20O2
• Molecular Mass: 232.3181
• Monoisotopic Mass: 232.14632988
• SMILES: O=C1O[C@@H]2C=C(CCC=C(CC[C@H]2C1=C)C)C
• Canonical SMILES: CC1=C[C@H]2OC(=O)C(=C)[C@@H]2CCC(=CCC1)C
• InChI: InChI=1S/C15H20O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h5,9,13-14H,3-4,6-8H2,1-2H3/t13-,14+/m0/s1
• InChIKey: HRYLQFBHBWLLLL-UONOGXRCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aS,11aR)-6,10-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one
• IUPAC Traditional name: costunolide; (3aS,11aR)-6,10-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-2-one
• Synonyms: Costunolide; Costunolide

Database IDs

• CAS Number: 553-21-9
• PubChem SID: 162221044
• PubChem CID: 5281437
• CHEBI ID: 3900
• CHEMBL: 205612
• Chemspider ID: 4444782
• MeSH Name: (+)-Costunolide
• Unique Ingredient Identifier: 4IK578SA7Z
• Wikipedia Title: Costunolide

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 3.8161666
• LogD (pH = 7.4): 3.8161666
• Log P: 3.8161666
• Molar Refractivity: 69.9464 cm^3
• Polarizability: 26.945713 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Cryst.

Pharmacology Properties

• Mechanism of Action: Activator of Nrf2 leading to HO-1 expression; Effective HO-1 inducer inhibiting macrophage-derived pro-inflammatory cytokines; Suppressive on cytotoxic T lymphocytes

Product Information

• Purity: 97.5
• Biological Source: Constit. of costus root (Saussurea lappa) and Artemisia balchanorum. Also from Talauma mexicana and Cosmos sulphureus
• Application(s): Shows antimycobacterial activity

REFERENCES

• Rao, A.S. et al., Tetrahedron, 1960, 9, 275, (isol)
• Bouill, M.J. et al., Acta Cryst. B, 1976, 32, 3203, (cryst struct)
• Kanasaki, T. et al., Agric. Biol. Chem., 1976, 40, 1239
• Grieco, P.A. et al., J.O.C., 1977, 42, 1717, (synth)
• Shibuya, H. et al., Chem. Lett., 1986, 85, (synth)
• Takahashi, T. et al., Tetrahedron, 1987, 43, 5499, (synth)
• Banerjee, A.K. et al., Tetrahedron, 1993, 49, 4761, (synth, rev)
• Taniguchi, M. et al., Biosci., Biotechnol., Biochem., 1995, 59, 2064-2067, (activity)
• Jacobsson, U. et al., Phytochemistry, 1995, 39, 839, (Costunolide, pmr, cmr)
• Park, H.-J. et al., J. Nat. Prod., 1996, 59, 1128, (Costunolide, pmr, cmr)
• Fischer, N.H. et al., Phytochemistry, 1998, 49, 559-564, (activity)
• Jang, D.S. et al., Saengyak Hakhoechi, 1998, 29, 67-70, (activity)