LIPID MAPS

Structure Database (LMSD)

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Common Name

LTC4-d5

Systematic Name

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

Synonyms

Leukotriene C4-d5

LM ID

LMFA03020088

Formula

C₃₀H₄₂D₅N₃O₉S

Exact Mass

Calculate m/z

630.334686

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View spectra on LIPID MAPS Standard Spectra DB

Classification

Biological Context

Leukotriene C4-d5 (LTC4-d5) contains five deuterium atoms at the 19, 19', 20, 20 and 20 positions. It is intended for use as an internal standard for the quantification of LTC4 by GC- or LC-mass spectrometry. LTC4 is the parent cysteinyl leukotriene produced by the LTC4 synthase catalyzed conjugation of glutathione to LTA4. LTC4 is produced by neutrophils, macrophages, and mast cells, and by transcellular metabolism in platelets.¹ It is one of the constituents of slow-reacting substance of anaphylaxis (SRS-A) and exhibits potent smooth muscle contracting activity.² LTC4-induced bronchoconstriction and enhanced vascular permeability contribute to the pathogenesis of asthma and acute allergic hypersensitivity.^3,4 The concentration of LTC4 required to produce marked contractions of lung parenchymal strips and isolated tracheal rings is about 1 nM.⁴

This information has been provided by Cayman Chemical

References

1. Maclouf, J.A., and Murphy, R.C. Transcellular metabolism of neutrophil-derived leukotriene A4 by human platelets. A potential cellular source of leukotriene C4. The Journal of Biological Chemisty 263(1), 174-181 (1988).

2. Piper, P.J. Formation and actions of leukotrienes. Physiol. Rev. 64(2), 744-761 (1984).

3. Samuelsson, B. Leukotrienes: Mediators of immediate hypersensitivity reactions and inflammation. Science 220(4597), 568-575 (1983).

4. 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)

GWNVDXQDILPJIG-IHTYDPOPSA-N

InChi (Click to copy)

InChI=1S/C30H47N3O9S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-25(24(34)15-14-17-27(36)37)43-21-23(29(40)32-20-28(38)39)33-26(35)19-18-22(31)30(41)42/h6-7,9-13,16,22-25,34H,2-5,8,14-15,17-21,31H2,1H3,(H,32,40)(H,33,35)(H,36,37)(H,38,39)(H,41,42)/b7-6-,10-9-,12-11+,16-13+/t22-,23-,24-,25+/m0/s1/i1D3,2D2

SMILES (Click to copy)

C(=O)(NCC(O)=O)[C@@H](NC(=O)CC[C@H](N)C(=O)O)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]