Structure Database (LMSD)

OH OH O O O OH
Common Name
8S,15S-diHPETE
Systematic Name
8S,15S-dihydroperoxy-5Z,9E,11Z,13E-eicosatetraenoic acid
Synonyms
LM ID
LMFA03060098
Formula
C20H32O6
Exact Mass
Calculate m/z
368.21989
Sum Composition
FA 20:4;O4
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Eicosanoids [FA03]
Hydroxy/hydroperoxyeicosatetraenoic acids [FA0306]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]

String Representations

InChiKey (Click to copy)
CXDIKCDVBUPCCG-HCCKYKKOSA-N
InChi (Click to copy)
InChI=1S/C20H32O6/c1-2-3-8-13-18(25-23)14-9-4-5-10-15-19(26-24)16-11-6-7-12-17-20(21)22/h4-6,9-11,14-15,18-19,23-24H,2-3,7-8,12-13,16-17H2,1H3,(H,21,22)/b5-4-,11-6-,14-9+,15-10+/t18-,19+/m0/s1
SMILES (Click to copy)
C(/C=C/[C@@H](OO)C/C=C\CCCC(=O)O)=C/C=C/[C@@H](OO)CCCCC

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

Other Databases

CHEBI ID
136400
PubChem CID
52921888

Calculated Physicochemical Properties

Heavy Atoms 26
Rings 0
Aromatic Rings 0
Rotatable Bonds 16
Van der Waals Molecular Volume 394.10
Topological Polar Surface Area 96.22
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 6
logP 6.07
Molar Refractivity 102.56

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Created at
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Updated at
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