(13R,14R)-13-(acetyloxy)-12,12-dimethyl-4-oxo-3,11-dioxatricyclo[8.4.0.02,7]tetradeca-1,5,7,9-tetraen-14-yl (2Z)-2-methylbut-2-enoate

• ChemBase ID: 179769
• Molecular Formular: C21H22O7
• Molecular Mass: 386.39518
• Monoisotopic Mass: 386.13655304
• SMILES: c12[C@H]([C@H](C(Oc2ccc2c1oc(=O)cc2)(C)C)OC(=O)C)OC(=O)/C(=C\C)/C
• Canonical SMILES: C/C=C(\C(=O)O[C@@H]1c2c(ccc3c2oc(=O)cc3)OC([C@@H]1OC(=O)C)(C)C)/C
• InChI: InChI=1S/C21H22O7/c1-6-11(2)20(24)27-18-16-14(28-21(4,5)19(18)25-12(3)22)9-7-13-8-10-15(23)26-17(13)16/h6-10,18-19H,1-5H3/b11-6-/t18-,19-/m1/s1
• InChIKey: LYUZYPKZQDYMEE-YRCPKEQFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (13R,14R)-13-(acetyloxy)-12,12-dimethyl-4-oxo-3,11-dioxatricyclo[8.4.0.0^2,^7]tetradeca-1,5,7,9-tetraen-14-yl (2Z)-2-methylbut-2-enoate
• IUPAC Traditional name: (13R,14R)-13-(acetyloxy)-12,12-dimethyl-4-oxo-3,11-dioxatricyclo[8.4.0.0^2,^7]tetradeca-1,5,7,9-tetraen-14-yl (2Z)-2-methylbut-2-enoate
• Synonyms: Pterixin; Pteryxin

Database IDs

• CAS Number: 13161-75-6
• PubChem SID: 164235679
• PubChem CID: 5281425

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.4674602
• LogD (pH = 7.4): 3.4674602
• Log P: 3.4674602
• Molar Refractivity: 100.5297 cm^3
• Polarizability: 39.08222 Å^3
• Polar Surface Area: 88.13 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Product Information

• Biological Source: Isol. from Pteryxia terebinthina, Ammi ursina, Musineon diviricatum and Seseli libanotis
• Application(s): Antiaggregant; Muscle-relaxant

REFERENCES

• Schroeder, H.D. et al., Chem. Ber., 1959, 92, 2338, (synth, isol)
• Soine, T.O. et al., J. Pharm. Sci., 1962, 51, 149, (Pteryxin, Suksdorfin)
• Shanbhag, S.N. et al., Tetrahedron, 1965, 21, 3591; 1967, 23, 1235, (isol)
• Lemmich, J. et al., Acta Chem. Scand., 1966, 20, 2497; 1971, 25, 529, (isol, synth, derivs)
• Bernotat-Wulf, H. et al., Helv. Chim. Acta, 1969, 52, 1165, (cryst struct, abs config)
• Yamada, Y. et al., Tet. Lett., 1974, 2513, (isol)
• Shaath, N.A. et al., J. Pharm. Sci., 1976, 65, 1028, (ms)
• Nielsen, B.E. et al., Phytochemistry, 1976, 15, 1049, (derivs)
• Murray, R.D.H. et al., Prog. Chem. Org. Nat. Prod., 1978, 35, 200; 1991, 58, 83, (rev, bibl)
• Gonzlez, A.G. et al., Phytochemistry, 1979, 18, 1021, (deriv)
• Murray, R.D.H. et al., The Natural Coumarins, J. Wiley, 1982, 400, (occur, rev)
• Hamburger, M. et al., Helv. Chim. Acta, 1984, 67, 1729, (deriv)
• Swager, T.M. et al., Phytochemistry, 1985, 24, 805-813, (derivs)
• Bal-Tembe, S. et al., Heterocycles, 1987, 26, 1239; 1989, 29, 1675, (synth)
• Reisch, J. et al., J.C.S. Perkin 1, 1994, 3251, (synth)
• Chen, I.-S. et al., Phytochemistry, 1996, 41, 525-530, (isol, derivs)