LIPID MAPS

Structure Database (LMSD)

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Common Name

(+/-)14,15-DiHETrE-d11

Systematic Name

14,15-dihydroxy-5Z,8Z,11Z-eicosatrienoic 16,16,17,17,18,18,19,19,20,20,20-d11 acid

Synonyms

LM ID

LMFA03050034

Formula

C₂₀H₂₃D₁₁O₄

Exact Mass

Calculate m/z

349.314755

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View spectra on LIPID MAPS Standard Spectra DB

Classification

Biological Context

(±)14,15-DiHET-d11 is intended for use as an internal standard for the quantification of 14(15)-DiHET by GC- or LC-MS. 14(R),15(R)-DiHET and 14(S),15(S)-DiHET are vicinal diols formed via enzymatic hydration of 14(15)-EET by cytosolic or soluble epoxide hydrolases.^1,2 14(R),15(R)-DiHET is produced at a greater proportion than 14(S),15(S)-DiHET by cytosolic epoxide hydrolase.¹

This information has been provided by Cayman Chemical

References

1. Zeldin, D.C., Kobayashi, J., Falck, J.R., et al. Regio- and enantiofacial selectivity of epoxyeicosatrienoic acid hydration by cytosolic epoxide hydrolase. The Journal of Biological Chemisty 268(9), 6402-6407 (1993).

2. Zhang, G., Kodani, S., and Hammock, B.D. Stabilized epoxygenated fatty acids regulate inflammation, pain, angiogenesis and cancer. Prog. Lipid Res. 53, 108-123 (2014).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Synthetic deuterated standard

String Representations

InChiKey (Click to copy)

SYAWGTIVOGUZMM-LNTVGFLJSA-N

InChi (Click to copy)

InChI=1S/C20H34O4/c1-2-3-12-15-18(21)19(22)16-13-10-8-6-4-5-7-9-11-14-17-20(23)24/h4,6-7,9-10,13,18-19,21-22H,2-3,5,8,11-12,14-17H2,1H3,(H,23,24)/b6-4-,9-7-,13-10-/i1D3,2D2,3D2,12D2,15D2

SMILES (Click to copy)

C(/C=C\C/C=C\CCCC(=O)O)/C=C\CC(O)C(O)C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])[2H]