Structure Database (LMSD)
Common Name
9-HODE
Systematic Name
9-hydroxy-10E,12Z-octadecadienoic acid
Synonyms
- 9-hydroxy-trans-10,cis-12-octadecadienoic acid
3D model of 9-HODE
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
(±)9-HODE is one of the two racemic monohydroxy fatty acids resulting from the non-enzymatic oxidation of linoleic acid. Approximately equal proportions of both isomers are found in mitochondrial and plasma membranes of rabbit reticulocytes.1,2 Oxidized LDL contains significant amounts of esterified 9- and 13-HpODEs and HODEs.3,4
This information has been provided by Cayman Chemical
References
1. 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. J. Biol. Chem. 267(20), 14183-14188 (1992).
2. Folcik, V.A., and Cathcart, M.K. Predominance of esterified hydroperoxy-linoleic acid in human monocyte-oxidized LDL. J. Lipid Res. 35(9), 1570-1582 (1994).
3. 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).
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).
String Representations
InChiKey (Click to copy)
NPDSHTNEKLQQIJ-ZJHFMPGASA-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+
SMILES (Click to copy)
C(CCCCCCC(=O)O)C(O)/C=C/C=C\CCCCC
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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