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Structure Database (LMSD)

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Common Name

8R,11S-DiHODE

Systematic Name

8R,11S-dihydroxy-9Z,12Z-octadecadienoic acid

Synonyms

LM ID

LMFA02000064

Formula

C₁₈H₃₂O₄

Exact Mass

Calculate m/z

312.23006

Sum Composition

FA 18:2;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

8(R),11(S)-DiHODE is a fungal oxylipin that has been found in Aspergillus.^1,2 It is formed via isomerization of an 8(R)-HpODE intermediate during the oxidation of linoleic acid in several species of Aspergillus.

This information has been provided by Cayman Chemical

References

1. Jernerén, F., Garscha, U., Hoffmann, I., et al. Reaction mechanism of 5,8-linoleate diol synthase, 10R-dioxygenase, and 8,11-hydroperoxide isomerase of Aspergillus clavatus. Biochim. Biophys. Acta 1801(4), 503-507 (2010).

2. Garscha, U., Jernerén, F., Chung, D., et al. Identification of dioxygenases required for Aspergillus development. Studies of products, stereochemistry, and the reaction mechanism. The Journal of Biological Chemisty 282(48), 34707-34718 (2007).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Stereoselective oxidation of regioisomeric octadecenoic acids by fatty acid dioxygenases.,
J Lipid Res, 2011

Pubmed ID: 21852690

DOI: 10.1194/jlr.M018259

String Representations

InChiKey (Click to copy)

PIQZTMSSBGKFNU-UZDJSAAESA-N

InChi (Click to copy)

InChI=1S/C18H32O4/c1-2-3-4-5-8-11-16(19)14-15-17(20)12-9-6-7-10-13-18(21)22/h8,11,14-17,19-20H,2-7,9-10,12-13H2,1H3,(H,21,22)/b11-8-,15-14-/t16-,17+/m0/s1

SMILES (Click to copy)

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