LBF20406CV09

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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	XPR8005
LipidMaps	LMFA03120005
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF20406CV09

20-Acetoxyclavulone I
Structural Information
Systematic Name	Methyl-4R- (5-cis,7-trans) -4-acetoxy-7- [ 2S-acetoxy-2- [cis-7-acetoxy-2-octenyl] -5-oxo-3-cyclopentenylidene ] -5-heptenoic acid
Common Name	20-Acetoxyclavulone I Methyl-4R- (5Z,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 -31.1°(C 0.09, 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 10900),288 nm( ε 13700) IguchiKet al.
IR Spectra	ν max(film)1735,1705,1640,and 1235cm-1 IguchiKet al.
NMR Spectra	1H-NMR(270MHz,CDCl3) δ ppm2.03(3H,s),2.05(6H,s),2.38(2H,t,J=7.5Hz),2.66(1H,dd,J=8,14.5Hz),3.00(1H,dd,J=7,14.5Hz),3.70(3H,s),4.04(2H,t,J=6.6Hz),5.22(1H,m),5.47(1H,m),5.79(1H,m),5.79(1H,m),5.84(1H,t,J=10.2Hz),6.42(1H,d,J=6.3Hz),6.58(1H,dd,J=10.2,12.5Hz),7.27(1H,d,J=12.5Hz), 7.47(1H,d,J=6.3Hz). IguchiKet al.13C-NMR(67.8MHz,CDCl3) δ ppm21.0(q,2C),21.3(q),25.6(t),27.3(t),28.5(t),29.0(t),29.8(t,2C),35.8(t),51.8(q),64.5(t),69.4(d),85.1(s),121.5(d),124.2(d),124.6(d),134.5(d),135.2(d),137.4(s),138.9(d),157.8(d),169.1(s),169.9(s),171.2(s),172.9(s),193.1(s). IguchiKet al.
Other Spectra	CD λ ext(EtOH)( Δ ε )nm 247(+2.6),290(-3.6). KikuchiHet al. IguchiKet al.
Chromatograms

Reported Metabolites, References
Biospecies ID Compound Name Reference Comment n.a. LBF20406CV09 See above. Iguchi_K et al. 1983 n.a. LBF20406CV09 See above. Kikuchi_H et al. 1983