Structure Database (LMSD)

Common Name
5S-HETE di-endoperoxide
Systematic Name
5S,15S-dihydroxy-9S,11R,8S,12S-diperoxy-6E,13E-eicosadienoic acid
Synonyms
LM ID
LMFA03000011
Formula
C20H34O8
Exact Mass
Calculate m/z
402.22537
Sum Composition
FA 20:3;O6
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Eicosanoids [FA03]
Other Eicosanoids [FA0300]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Hydroxy fatty acids [FA0105]
Carbocyclic fatty acids [FA0114]

References

Reference
Convergence of the 5-LOX and COX-2 pathways:
heme-catalyzed cleavage of the 5S-HETE-derived di-endoperoxide into aldehyde fragments.
Griesser M, Boeglin WE, Suzuki T, Schneider C.
J Lipid Res. 2009 Dec;50(12):2455-62

String Representations

InChiKey (Click to copy)
DOXGUXRZAOCYPM-IPIAXWAYSA-N
InChi (Click to copy)
InChI=1S/C20H34O8/c1-2-3-4-6-14(21)9-11-16-18-13-19(28-27-18)17(26-25-16)12-10-15(22)7-5-8-20(23)24/h10,12,14-19,21-22H,2-9,11,13H2,1H3,(H,23,24)/b12-10+/t14-,15-,16-,17-,18+,19-/m0/s1
SMILES (Click to copy)
[C@@H]12OO[C@@H]([C@H](CC[C@@H](O)CCCCC)OO[C@H]1/C=C/[C@@H](O)CCCC(=O)O)C2

Other Databases

CHEBI ID
138496
PubChem CID
52921873

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 2
Aromatic Rings 0
Rotatable Bonds 13
Van der Waals Molecular Volume 394.88
Topological Polar Surface Area 122.96
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 8
logP 4.39
Molar Refractivity 103.20

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Updated at
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