Structure Database (LMSD)
Common Name
9S-HODE
Systematic Name
9S-hydroxy-10E,12Z-octadecadienoic acid
Synonyms
- 10,12-Octadecadienoic acid, 9-hydroxy-, [S-(E,Z)]-
- alpha-Dimorphecolic acid
3D model of 9S-HODE
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
9(S)-HODE is a metabolite of the ω-6 polyunsaturated fatty acid linoleic acid .1,2 It is formed from linoleic acid by lipoxygenases. 9(S)-HODE (68 µM) increases transactivation of peroxisome proliferator-activated receptor α (PPARα) and PPARγ in reporter assays using mouse aortic endothelial cells.3 It induces chemotaxis of primary human monocytes when used at a concentration of 10 µM.4 9(S)-HODE has been found in oxidized LDL (oxLDL).5
This information has been provided by Cayman Chemical
References
1. Gardner, H.W. Soybean lipoxygenase-1 enzymically forms both (9S)- and (13S)-hydroperoxides from linoleic acid by a pH-dependent mechanism. Biochim. Biophys. Acta 1001(3), 274-281 (1989).
2. Kühn, H., Belkner, J., and Wiesner, R. Subcellular distribution of lipoxygenase products in rabbit reticulocyte membranes. Eur. J. Biochem. 191(1), 221-227 (1990).
3. Ku, G., Thomas, C.E., Akeson, A.L., et al. Induction of interleukin 1β expression from human peripheral blood monocyte-derived macrophages by 9-hydroxyoctadecadienoic acid. The Journal of Biological Chemisty 267(20), 14183-14188 (1992).
4. Hourton, D., Delerive, P., Stanková, J., et al. Oxidized low-density lipoprotein and peroxisome-proliferator-activated receptor α down-regulate platelet-activating-factor receptor expression in human macrophages. Biochem. J. 354(Pt 1), 225-232 (2001).
5. Rolin, J., Vego, H., and Maghazachi, A.A. Oxidized lipids and lysophosphatidylcholine induce the chemotaxis, up-regulate the expression of CCR9 and CXCR4 and abrogate the release of IL-6 in human monocytes. Toxins (Basel) 6(9), 2840-2856 (2014).
String Representations
InChiKey (Click to copy)
NPDSHTNEKLQQIJ-UINYOVNOSA-N
InChi (Click to copy)
InChI=1S/C18H32O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14,17,19H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6-,14-11+/t17-/m1/s1
SMILES (Click to copy)
C(CCCCCCC[C@H](O)/C=C/C=C\CCCCC)(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
21
Rings
0
Aromatic Rings
0
Rotatable Bonds
14
Van der Waals Molecular Volume
338.41
Topological Polar Surface Area
57.53
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
3
logP
5.14
Molar Refractivity
88.90
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Updated at
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