Structure Database (LMSD)

Common Name
13-Oxo-ODE-d3
Systematic Name
13-oxo-9Z,11E-9,10,12-d3-octadecadienoic acid
Synonyms
  • 13-KODE-d3
  • 13-keto-9Z,11E-9,10,12-d3-octadecadienoic acid
LM ID
LMFA02000454
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

13-OxoODE-d3 contains three deuterium atoms at the 9, 10, and 12 positions. It is intended for use as an internal standard for the quantification of 13-OxoODE by GC- or LC-mass spectrometry. 13-oxoODE is produced from 13-HODE by a NAD+-dependent dehydrogenase present in rat colonic mucosa.1 13-OxoODE stimulates cell proliferation when instilled intrarectally in rats.2 13-OxoODE has also been detected in preparations of rabbit reticulocyte plasma and mitochondrial membranes, mostly esterified to phospholipids. Production of 13-oxoODE is putatively linked to the maturation of reticulocytes to erythrocytes through the activity of 15-LO.3,4

This information has been provided by Cayman Chemical

References

1. Earles, S.M., Bronstein, J.C., Winner, D.L., et al. Metabolism of oxidized linoleic acid: Characterization of 13-hydroxyoctadecadienoic acid dehydrogenase activity from rat colonic tissue. Biochim. Biophys. Acta 1081, 174-180 (1991).
2. Bull, A.W., and Bronstein, J.C. Production of unsaturated carbonyl compounds during metabolism of hydroperoxy fatty acids by colonic homogenates. Carcinogenesis 11, 1699-1704 (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).
4. Kühn, H., Belkner, J., and Wiesner, R. Subcellular distribution of lipoxygenase products in rabbit reticulocyte membranes. Eur. J. Biochem. 191(1), 221-227 (1990).

References

Taxonomy Information

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

String Representations

InChiKey (Click to copy)
JHXAZBBVQSRKJR-POQBIENVSA-N
InChi (Click to copy)
InChI=1S/C18H30O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)/b9-7-,15-12+/i7D,9D,15D
SMILES (Click to copy)
C(CCCCCCC/C(/[2H])=C(/[2H])\C=C(/[2H])\C(=O)CCCCC)(=O)O

Other Databases

PubChem CID
168322904
Cayman ID
338620

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