(3aS,6S,6aR,9aS,9bR)-6a-hydroxy-6,9a-dimethyl-3-methylidene-dodecahydroazuleno[4,5-b]furan-2,9-dione

• ChemBase ID: 179735
• Molecular Formular: C15H20O4
• Molecular Mass: 264.3169
• Monoisotopic Mass: 264.13615912
• SMILES: [C@@]12([C@@H]3OC(=O)C(=C)[C@@H]3CC[C@@H]([C@@]1(CCC2=O)O)C)C
• Canonical SMILES: O=C1O[C@@H]2[C@H](C1=C)CC[C@@H]([C@]1([C@@]2(C)C(=O)CC1)O)C
• InChI: InChI=1S/C15H20O4/c1-8-4-5-10-9(2)13(17)19-12(10)14(3)11(16)6-7-15(8,14)18/h8,10,12,18H,2,4-7H2,1,3H3/t8-,10-,12+,14-,15+/m0/s1
• InChIKey: GEUJJEYGSRWXPC-JISBIHODSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aS,6S,6aR,9aS,9bR)-6a-hydroxy-6,9a-dimethyl-3-methylidene-dodecahydroazuleno[4,5-b]furan-2,9-dione
• IUPAC Traditional name: (3aS,6S,6aR,9aS,9bR)-6a-hydroxy-6,9a-dimethyl-3-methylidene-dodecahydroazuleno[4,5-b]furan-2,9-dione
• Synonyms: 1,2-Dihydroparthenin; Coronopilin

Database IDs

• CAS Number: 2571-81-5
• PubChem SID: 164235645
• PubChem CID: 257278

CALCULATED PROPERTIES

• Acid pKa: 13.925014
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.1128993
• LogD (pH = 7.4): 2.112899
• Log P: 2.1128993
• Molar Refractivity: 68.4102 cm^3
• Polarizability: 27.41733 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Product Information

• Biological Source: Constit. of Parthenium incanum, Ambrosia psilostachya, Ambrosia artemisiifolia, Iva nevadensis and Iva acerosa
• Application(s): Antiinflamatory agent; Antineoplastic

REFERENCES

• Herz, W. et al., J.O.C., 1961, 26, 5011, (Coronopilin)
• Herz, W. et al., J.A.C.S., 1962, 84, 2601, (isol, struct, pharmacol)
• Geissman, T.A. et al., J.O.C., 1964, 29, 2553, (Coronopilin)
• Kok, P. et al., Bull. Soc. Chim. Belg., 1978, 87, 615, (synth)
• Heathcock, C.H. et al., J.A.C.S., 1982, 104, 6081, (synth)
• Balza, F. et al., Phytochemistry, 1988, 27, 1421; 1787, (isol, pmr, cmr)
• Hooper, M. et al., Eur. J. Med. Chem. (Chim. Ther.), 1990, 25, 717, (antimalarial props)
• Asaoka, M. et al., Tetrahedron, 1995, 51, 3115, (synth)
• Shimoma, F. et al., J.O.C., 1998, 63, 3758-3763, (synth)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, PAM175