LBF20406CV10

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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	XPR8006
LipidMaps	LMFA03120006
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF20406CV10

20-Acetoxyclavulone II
Structural Information
Systematic Name	Methyl-4R- (5-trans,7-trans) -4-acetoxy-7- [ 2S-acetoxy-2- [cis-7-acetoxy-2-octenyl] -5-oxo-3-cyclopentenylidene ] -5-heptenoic acid
Common Name	20-Acetoxyclavulone II Methyl-4R- (5E,7E) -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 +3.7°(C 0.54, 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 14200),292 nm( ε 18700) IguchiKet al.
IR Spectra	ν max(film)1730,1700,1640,and 1235cm-1 IguchiKet al.
NMR Spectra	1H-NMR(270MHz,CDCl3) δ ppm2.05(3H,s),2.07(3H,s),2.08(3H,s),2.38(2H,t,J=7.3Hz),2.69(1H,dd,J=7.6,16Hz),2.87(1H,dd,J=7.3,16Hz),3.68(3H,s),4.04(2H,t,J=6.9Hz),5.20(1H,m),5.41(1H,q,J=7Hz),5.51(1H,dt,J=11,7.3Hz),6.03(1H,dd,J=7,14.8Hz),6.41(1H,d,J=6.9Hz),6.74(1H,dd,J=12.2,14.8Hz),6.86(1H,d,J=12.2Hz),7.47(1H,d,J=5.9Hz). IguchiKet al.13C-NMR(67.8MHz,CDCl3) δ ppm21.0(q,2C),21.2(q),25.6(t),27.3(t),28.5(t),29.2(t,2C),29.5(t),36.0(t),51.8(q),64.4(t),72.8(d),85.0(s),121.5(d),126.8(d),129.3(d),134.5(d),135.0(d),136.8(s),141.3(d),158.1(d),169.5(s),169.9(s),171.2(s),172.9(s),193.3(s). IguchiKet al.
Other Spectra	CD λ ext(EtOH)( Δ ε )nm 247(+2.6),295(-1.0). KikuchiHet al. IguchiKet al.
Chromatograms

Reported Metabolites, References
Biospecies ID Compound Name Reference Comment n.a. LBF20406CV10 See above. Iguchi_K et al. 1983 n.a. LBF20406CV10 See above. Kikuchi_H et al. 1983