Structure Database (LMSD)

OH O OH O OH O
Common Name
5S,15S-diHPETE
Systematic Name
5S,15S-dihydroperoxy-6E,8Z,11Z,13E-eicosatetraenoic acid
Synonyms
LM ID
LMFA03060097
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)
PCIOUQYHTPPZEM-BVHTXILBSA-N
InChi (Click to copy)
InChI=1S/C20H32O6/c1-2-3-9-13-18(25-23)14-10-7-5-4-6-8-11-15-19(26-24)16-12-17-20(21)22/h5-8,10-11,14-15,18-19,23-24H,2-4,9,12-13,16-17H2,1H3,(H,21,22)/b7-5-,8-6-,14-10+,15-11+/t18-,19+/m0/s1
SMILES (Click to copy)
C(/C=C\C=C\[C@@H](OO)CCCC(=O)O)/C=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
138291
PubChem CID
52921887

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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