LIPID MAPS

Structure Database (LMSD)

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Common Name

(+/-)5,6-EpETrE-d11

Systematic Name

(+/-)5(6)-epoxy-8Z,11Z,14Z-eicosatrienoic-16,16,17,17,18,18,19,19,20,20,20-d11

Synonyms

5(6)-EET-d11

LM ID

LMFA03080026

Formula

C₂₀H₂₁D₁₁O₃

Exact Mass

Calculate m/z

331.30419

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View spectra on LIPID MAPS Standard Spectra DB

Classification

Biological Context

(±)5(6)-EET-d11 is intended for use as an internal standard for the quantification of 5(6)-EET by GC- or LC-MS. 5(S),6(R)-EET and 5(R),6(S)-EET are formed via epoxidation of arachidonic acid by a variety of cytochrome P450 (CYP) isoforms, including CYP2B1, CYP2B2, CYP2C11, CYP2C23, and CYP2C24.1,2

This information has been provided by Cayman Chemical

References

1. Spector, A.A., and Norris, A.W. Action of epoxyeicosatrienoic acids on cellular function. Am. J. Physiol. Cell Physiol. 292(3), C996-C1012 (2007).

2. Capdevila, J.H., Falck, J.R., and Harris, R.C. Cytochrome P450 and arachidonic acid bioactivation: Molecular and functional properties of the arachidonate monooxygenase. J. Lipid Res. 41(2), 163-181 (2000).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Synthetic deuterated standard

String Representations

InChiKey (Click to copy)

VBQNSZQZRAGRIX-UAPSQRHXSA-N

InChi (Click to copy)

InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-10,12-13,18-19H,2-5,8,11,14-17H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-/i1D3,2D2,3D2,4D2,5D2

SMILES (Click to copy)

C(/C=C\CC1OC1CCCC(=O)O)/C=C\C/C=C\C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])[2H]