LIPID MAPS

Structure Database (LMSD)

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Common Name

LTD4-d5

Systematic Name

5S-hydroxy-6R-(S-cysteinylglycinyl)),7E,9E,11Z,14Z-eicosatetraenoic-19,19,20,20,20-d5 acid

Synonyms

Leukotriene D4-d5

LM ID

LMFA03020089

Formula

C₂₅H₃₅D₅N₂O₆S

Exact Mass

Calculate m/z

501.292092

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View spectra on LIPID MAPS Standard Spectra DB

Classification

Biological Context

Leukotriene D4-d5 (LTD4-d5) is intended for use as an internal standard for the quantification of LTD4 by GC- or LC-MS. LTD4 is an active metabolite of LTC4 and a constituent of slow-reacting substance of anaphylaxis (SRS-A).^1,2 It is formed via metabolism of LTC4 by γ-glutamyl transpeptidase. Like LTC4, LTD4 (0.01-0.1 pM) induces contractions in isolated guinea pig parenchymal strips and tracheal spirals.³ In vivo, LTD4 increases insufflation pressure, a marker of bronchoconstriction, in anesthetized guinea pigs by 100% when administered at a dose of 89 pmol per animal.⁴ It also increases vascular permeability in guinea pig skin when administered intradermally at a dose of 0.1 pmol per animal.

This information has been provided by Cayman Chemical

References

1. Örning, L., Hammarström, S., and Samuelsson, B. Leukotriene D: A slow reacting substance from rat basophilic leukemia cells. Proc. Natl. Acad. Sci. USA 77(4), 2014-2017 (1980).

2. Hammarström, S., Örning, L., and Bernström, K. Metabolism of leukotrienes. Mol. Cell Biochem. 69(1), 7-16 (1985).

3. Lefer, A.M. Leukotrienes as mediators of ischemia and shock. Biochem. Pharmacol. 35(2), 123-127 (1986).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Synthetic deuterated standard

String Representations

InChiKey (Click to copy)

YEESKJGWJFYOOK-HXHZKDJLSA-N

InChi (Click to copy)

InChI=1S/C25H40N2O6S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-22(21(28)15-14-17-23(29)30)34-19-20(26)25(33)27-18-24(31)32/h6-7,9-13,16,20-22,28H,2-5,8,14-15,17-19,26H2,1H3,(H,27,33)(H,29,30)(H,31,32)/b7-6-,10-9-,12-11+,16-13+/t20-,21-,22+/m0/s1/i1D3,2D2

SMILES (Click to copy)

C(=O)(NCC(O)=O)[C@@H](N)CS[C@@H]([C@@H](O)CCCC(O)=O)/C=C/C=C/C=C\C/C=C\CCCC([2H])([2H])C([2H])([2H])[2H]