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Structure Database (LMSD)

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Common Name

13R-HODE

Systematic Name

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

Synonyms

Coriolic acid

LM ID

LMFA02000035

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

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Classification

Biological Context

13(R)-HODE is the opposite enantiomer of the 13(S)-HODE produced when linoleic acid is incubated with soybean lipoxygenase. The presence of 13(R)-HODE in the supernatants and membranes of cultured bovine endothelial cells has been attributed to COX metabolism.¹ 13(R)-HODE is a weak (IC50 = 2.7 µM) inhibitor of U-46619-induced platelet aggregation.²

This information has been provided by Cayman Chemical

References

1. Lagarde, M., Boutillon, M.M., Guichardant, M., et al. Further studies on the anti-thromboxane A2 activity of monohydroxylated fatty acids. Biochem. Pharmacol. 38, 1863-1864 (1989).

2. Baer, A.N., Costello, P.B., and Green, F.A. Stereospecificity of the hydroxyeicosatetraenoic and hydroxyoctadecadienoic acids produced by cultured bovine endothelial cells. Biochim. Biophys. Acta 1085(1), 45-52 (1991).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Bos taurus (#9913)

Mammalia (#40674)

Stereospecificity of the hydroxyeicosatetraenoic and hydroxyoctadecadienoic acids produced by cultured bovine endothelial cells.,
Biochim Biophys Acta, 1991

Pubmed ID: 1892877

Coriaria (#3459)

Magnoliopsida (#3398)

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

Pubmed ID: 17805822

String Representations

InChiKey (Click to copy)

HNICUWMFWZBIFP-PIHGWCCBSA-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-/m1/s1

SMILES (Click to copy)

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