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Structure Database (LMSD)

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Common Name

9S-HOTrE

Systematic Name

9S-hydroxy-10E,12Z,15Z-octadecatrienoic acid

Synonyms

9-HOTrE

LM ID

LMFA02000024

Formula

C₁₈H₃₀O₃

Exact Mass

Calculate m/z

294.219495

Sum Composition

FA 18:3;O

Status

Curated

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Classification

Biological Context

9(S)-HOTrE is a monohydroxy polyunsaturated fatty acid produced by the action of 5-lipoxygenase on α-linolenic acid.¹ 9(S)-HOTrE is predominantly localized in cellular ester lipids of Glechoma hederacea leaves and is partially released during artificial dehydration.² The biological role of 9(S)-HOTrE in G. hederacea leaves is still undetermined, but it may play a role in natural senescence.² 9(S)-HOTrE is an inhibitor of spore germination and germ tube elongation of rice blast fungus with ED50 values of 45 and 30 ppm, respectively.³

This information has been provided by Cayman Chemical

References

1. Namai, T., Kato, T., Yamaguchi, Y., et al. Anti-rice blast activity and resistance induction of C-18 oxygenated fatty acids. Biosci. Biotechnol. Biochem. 57, 611-613 (1993).

2. Kühn, H., Wisner, R., Alder, L., et al. Occurrence of free and esterified lipoxygenase products in leaves of Glechoma hederacea L. and other Labiatae. Eur. J. Biochem. 186, 155-162 (1989).

3. Galliard, T., and Phillips, D.R. Lipoxygenase from potato tubers. Partial purification and properties of an enzyme that specifically oxygenates the 9-position of linoleic acid. Biochem. J. 124, 431-438 (1971).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010

Pubmed ID: 20671299

DOI: 10.1194/jlr.M009449

String Representations

InChiKey (Click to copy)

RIGGEAZDTKMXSI-MEBVTJQTSA-N

InChi (Click to copy)

InChI=1S/C18H30O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h3-4,6,8,11,14,17,19H,2,5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b4-3-,8-6-,14-11+/t17-/m1/s1

SMILES (Click to copy)

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