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Structure Database (LMSD)

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Common Name

13S-HODE

Systematic Name

13S-hydroxy-9Z,11E-octadecadienoic acid

Synonyms

(9Z, 11E)-(13S)-13-Hydroxyoctadeca-9,11-dienoic acid
13-HODE

LM ID

LMFA02000228

Formula

C₁₈H₃₂O₃

Exact Mass

Calculate m/z

296.235145

Sum Composition

FA 18:2;O

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

13(S)-HODE is produced by incubation of linoleic acid with plant and mammalian lipoxygenases. It has been shown to inhibit the adhesion of tumor cells to the endothelium at concentrations around 1 µM,1,2 and down regulates the expression of the IRGpIIb/IIIa receptor.³

This information has been provided by Cayman Chemical

References

1. Grossi, I.M., Fitzgerald, L.A., Umbarger, L.A., et al. Bidirectional control of membrane expression and/or activation of the tumor cell IRGpIIb/IIIa receptor and tumor cell adhesion by lipoxygenase products of arachidonic acid and linoleic acid. Cancer Res. 49(4), 1029-1037 (1989).

2. Buchanan, M.R., Haas, T.A., Lagarde, M., et al. 13-Hydroxyoctadecadienoic acid is the vessel wall chemorepellant factor, LOX. The Journal of Biological Chemisty 260(30), 16056-16059 (1985).

3. Honn, K.V., Nelson, K.K., Renaud, C., et al. Fatty acid modulation of tumor cell adhesion to microvessel endothelium and experimental metastasis. Prostaglandins 44(5), 413-429 (1992).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Metabolism of oxidized linoleic acid by glutathione transferases: peroxidase activity toward 13-hydroperoxyoctadecadienoic acid.,
Biochim Biophys Acta, 2006

Pubmed ID: 16624487

Coriaria myrtifolia (#3460)

Magnoliopsida (#3398)

Structure and intraglyceride distribution of coriolic acid.,
Lipids, 1968

Pubmed ID: 17805822

String Representations

InChiKey (Click to copy)

HNICUWMFWZBIFP-IRQZEAMPSA-N

InChi (Click to copy)

InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15,17,19H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)/b9-7-,15-12+/t17-/m0/s1

SMILES (Click to copy)

OC(=O)CCCCCCC/C=C\C=C\[C@@H](O)CCCCC