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Structure Database (LMSD)

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Common Name

8R-HETE

Systematic Name

8R-hydroxy-5Z,9E,11Z,14Z-eicosatetraenoic acid

Synonyms

8-HETE

LM ID

LMFA03060021

Formula

C₂₀H₃₂O₃

Exact Mass

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320.235146

Sum Composition

FA 20:4;O

Status

Curated

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Classification

Biological Context

8(R)-HETE is biosynthesized by lipoxygenation of arachidonic acid in marine invertebrates such as gorgonian corals and starfish.^1,2 Stereochemical assignment of the (R) enantiomer is based on comparison of chiral HPLC retention times to published results. 3

This information has been provided by Cayman Chemical

References

1. Schneider, C., Yu, Z., Boeglin, W.E., et al. Enantiomeric separation of hydroxy and hydroperoxy eicosanoids by chiral column chromatography. Methods Enzymol. 433, 145-157 (2007).

2. Brash, A.R., Baertschi, S.W., Ingram, C.D., et al. On non-cyclooxygenase prostaglandin synthesis in the sea whip coral, Plexaura Homomalla: An 8(R)-lipoxygenase pathway leads to formation of an α-ketol and a racemic prostanoid. J. Biol. Chem. 262(33), 15829-15839 (1987).

3. Meijer, L., Brash, A.R., Bryant, R.W., et al. Stereospecific induction of starfish oocyte maturation by (8R)-hydroxyeicosatetraenoic acid. J. Biol. Chem. 261(36), 17040-17047 (1986).

String Representations

InChiKey (Click to copy)

NLUNAYAEIJYXRB-GTYUHVKWSA-N

InChi (Click to copy)

InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-13-16-19(21)17-14-11-12-15-18-20(22)23/h6-7,9-11,13-14,16,19,21H,2-5,8,12,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,14-11-,16-13+/t19-/m0/s1

SMILES (Click to copy)

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