LBF20406CV11

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Fatty acid (脂肪酸)

Glycerolipid (グリセロ脂質)

Sphingolipid (スフィンゴ脂質)

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Upper classes: LB LBF

IDs and Links
LipidBank	XPR8007
LipidMaps	LMFA03120007
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF20406CV11

20-Acetoxyclavulone III
Structural Information
Systematic Name	Methyl-4R- (5-trans,7-cis) -4-acetoxy-7- [ 2S-acetoxy-2- [cis-7-acetoxy-2-octenyl] -5-oxo-3-cyclopentenylidene ] -5-heptenoic acid
Common Name	20-Acetoxyclavulone III Methyl-4R- (5E,7Z) -4-acetoxy-7- [ 2S-acetoxy-2- [(Z)-7-acetoxy-2-octenyl] -5-oxo-3-cyclopentenylidene ] -5-heptenoic acid
Symbol
Formula	C27H36O9
Exact Mass	504.23593274999996
Average Mass	504.56934
SMILES	C(C[C@](OC(C)=O)(C=1)C(=CC=C[C@@H](CCC(=O)OC)OC(C)=O)C(=O)C1)=CCCCCCOC(C)=O
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation	[ α ]D +26.4°(C 0.86, CHCl3) IguchiKet al.
Refractive Index
Solubility	20-Acetoxyclavulones are soluble in MeOH, EtOH, CHCl3, or hexane.
Source	20-Acetoxyclavulones were isolated from Japanese soft coral, Stolonifer Clavularia viridis Quoy and Gaimard. Iguchi_K et al.
Chemical Synthesis
Metabolism
Biological Activity	20-Acetoxyclavulones showed a significant anti-inflammatory effect at 30 mu g/ml by the fertile egg test. Kikuchi_H et al.
Genetic Information
Note
Spectral Information
Mass Spectra
UV Spectra	λ max(EtOH) 230 nm( ε 12400),295 nm( ε 12100) IguchiKet al.
IR Spectra	ν max(film)1730,1695,1640,and 1235cm-1 IguchiKet al.
NMR Spectra	1H-NMR(270MHz,CDCl3) δ ppm2.02(3H,s),2.05(3H,s),2.10(3H,s),2.39(2H,t,J=7.6Hz),2.62(1H,dd,J=7.6,14.2Hz),2.87(1H,dd,J=7.3,14.2Hz),3.68(3H,s),4.04(2H,t,J=6.9Hz),5.21(1H,m),5.44(1H,q,J=5.9Hz),5.51(1H,m),6.03(1H,dd,J=5.9,15.5Hz),6.36(1H,d,J=6.3Hz),6.52(1H,d,J=11.2Hz),7.50(1H,d,J=6.3Hz),7.47(1H,dd,J=11.2,15.5Hz). IguchiKet al.13C-NMR(67.8MHz,CDCl3) δ ppm21.0(q,2C),21.7(q),25.6(t),27.3(t),28.5(t),29.0(t),29.2(t),29.8(t),35.6(t),51.7(q),64.4(t),72.5(d),85.2(s),121.8(d),126.4(d),133.5(d),134.2(d),135.6(s),136.9(d),141.1(d),156.0(d),169.9(s),170.1(s),171.2(s),173.1(s),194.0(s). IguchiKet al.
Other Spectra	CD λ ext(EtOH)( Δ ε )nm 243(+2.5),291(-0.6). KikuchiHet al. IguchiKet al.
Chromatograms

Reported Metabolites, References
Biospecies ID Compound Name Reference Comment n.a. LBF20406CV11 See above. Iguchi_K et al. 1983 n.a. LBF20406CV11 See above. Kikuchi_H et al. 1983