Structure Database (LMSD)

Common Name
9-Oxo-ODE-d3
Systematic Name
9-oxo-10E,12Z-10,12,13-d3-octadecadienoic acid
Synonyms
  • 9-KODE-d3
LM ID
LMFA02000455
Formula
C18H27D3O3
Exact Mass
Calculate m/z
297.238326
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View spectra on LIPID MAPS Standard Spectra DB

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Octadecanoids [FA02]
Other Octadecanoids [FA0200]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Oxo fatty acids [FA0106]

Biological Context

9-OxoODE-d3 contains three deuterium atoms at the 10, 12, and 13 positions. It is intended for use as an internal standard for the quantification of 9-OxoODE by GC- or LC-mass spectrometry. 9-OxoODE results from oxidation of the allylic hydroxyl of either 9(S)- or 9(R)-HODE. Rabbit reticulocyte plasma and mitochondrial membranes contain both 9- and 13-oxoODEs, representing about 2% of the total linoleate residues in the membranes. Most of these oxidized linoleate residues are esterified to membrane lipids.1,2,3

This information has been provided by Cayman Chemical

References

1. Kühn, H., Belkner, J., and Wiesner, R. Subcellular distribution of lipoxygenase products in rabbit reticulocyte membranes. Eur. J. Biochem. 191(1), 221-227 (1990).
2. Kühn, H., Belkner, J., and Wiesner, R. Metabolism of polyenoic fatty acids by rabbit reticulocytes. Intracellular action of the erythroid lipoxygenase on membrane lipids. Biomedica Biochimica Acta 49, S25-S30 (1990).
3. Kühn, H., Belkner, J., Wiesner, R., et al. Occurrence of 9- and 13-keto-octadecadienoic acid in biological membranes oxygenated by the reticulocyte lipoxygenase. Arch. Biochem. Biophys. 279, 218-224 (1990).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Synthetic deuterated standard

String Representations

InChiKey (Click to copy)
LUZSWWYKKLTDHU-NWDBFPNJSA-N
InChi (Click to copy)
InChI=1S/C18H30O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6-,14-11+/i6D,8D,14D
SMILES (Click to copy)
OC(=O)CCCCCCCC(=O)/C(/[2H])=C/C(/[2H])=C(/[2H])\CCCCC

Other Databases

PubChem CID
162640773
Cayman ID
338420

Calculated Physicochemical Properties

Heavy Atoms 21
Rings
Aromatic Rings
Rotatable Bonds 14
Van der Waals Molecular Volume 335.77
Topological Polar Surface Area 54.37
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 3
logP 5.06
Molar Refractivity 87.38

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Created at
3rd Dec 2024
Updated at
5th Dec 2024