Structure Database (LMSD)

Common Name
14,15-LTD4
Systematic Name
15S-hydroxy,14R-(S-cysteinylglycinyl)-5Z,8Z,10E,12E-eicosatetraenoic acid
Synonyms
  • 14,15-Leukotriene D4
  • EXD4
LM ID
LMFA03020032
Formula
C25H40N2O6S
Exact Mass
Calculate m/z
496.260709
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View spectra on LIPID MAPS Standard Spectra DB

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Eicosanoids [FA03]
Leukotrienes [FA0302]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Hydroxy fatty acids [FA0105]
Amino fatty acids [FA0110]

Biological Context

14,15-Leukotriene D4 (14,15-LTD4) is a member of an alternate class of LTs synthesized by a pathway involving the dual actions of 15- and 12-lipoxygenases (15- and 12-LOs) on arachidonic acid via 15-HpETE and 14,15-LTA4 intermediates.1,2,3,4 14,15-LTD4 is classified as an eoxin (EXD4), because it is formed mostly by eosinophils.3 However, mast cells and nasal polyps can synthesize 14,15-LTD4 as well. Little is known about the physiological actions of 14,15-LTD4. It has weak contractile activity on both guinea pig ileum and pulmonary parenchyma in contrast to the effects of 5-LO-derived LTs.5,6 However, in an in vitro permeability assay, 14,15-LTD4 can increase vascular permeability of human endothelial cell monolayers, with similar potency to that of 5-LO-derived LTs, resulting in plasma leakage, a hallmark of inflammation.3

This information has been provided by Cayman Chemical

References

1. Feltenmark, S., Gautam, N., Brunnström, Å., et al. Eoxins are proinflammatory arachidonic acid metabolites produced via the 15-lipoxygenase-1 pathway in human eosinophils and mast cells. Proc. Natl. Acad. Sci. USA 105(2), 680-685 (2008).
2. Sala, A., Civelli, M., Oliva, D., et al. Contractile and binding activities of structural analogues of LTC4 in the longitudinal muscle of guinea-pig ileum. Eicosanoids 3(2), 105-110 (1990).
3. Sailesh, S., Kumar, Y.V.K., Prasad, M., et al. Sheep uterus dual lipoxygenase in the synthesis of 14,15-leukotrienes. Arch. Biochem. Biophys. 315(2), 362-368 (1994).
4. Drazen, J.M., Lewis, R.A., Austen, K.F., et al. Contractile activities of structural analogs of leukotrienes C and D: Necessity of a hydrophobic region. Proc. Natl. Acad. Sci. USA 78(5), 3195-3198 (1987).
5. Yokoyama, C., Shinjo, F., Yoshimoto, T., et al. Arachidonate 12-lipoxygenase purified from porcine leukocytes by immunoaffinity chromatography and its reactivity with hydroperoxyeicosatetraenoic acids. J. Biol. Chem. 261(35), 16714-16721 (1986).
6. Bryant, R.W., Schewe, T., Rapoport, S.M., et al. Leukotriene formation by a purified reticulocyte lipoxygenase enzyme. Conversion of arachidonic acid and 15-hydroperoxyeicosatetraenoic acid to 14,15-leukotriene A4. J. Biol. Chem. 260(6), 3548-3555 (1985).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
On the biosynthesis and biological role of eoxins and 15-lipoxygenase-1 in airway inflammation and Hodgkin lymphoma.,
Prostaglandins Other Lipid Mediat, 2009
Pubmed ID: 19130894

String Representations

InChiKey (Click to copy)
BUTLPEVGZIRJOA-SPCGXPCUSA-N
InChi (Click to copy)
InChI=1S/C25H40N2O6S/c1-2-3-12-15-21(28)22(34-19-20(26)25(33)27-18-24(31)32)16-13-10-8-6-4-5-7-9-11-14-17-23(29)30/h4,6-10,13,16,20-22,28H,2-3,5,11-12,14-15,17-19,26H2,1H3,(H,27,33)(H,29,30)(H,31,32)/b6-4-,9-7-,10-8+,16-13+/t20-,21-,22+/m0/s1
SMILES (Click to copy)
C(CCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](N)C(=O)NCC(O)=O)[C@@H](O)CCCCC)(=O)O

Other Databases

CHEBI ID
63985
PubChem CID
42607304
Cayman ID
10011361

Calculated Physicochemical Properties

Heavy Atoms 34
Rings 0
Aromatic Rings 0
Rotatable Bonds 20
Van der Waals Molecular Volume 515.83
Topological Polar Surface Area 149.95
Hydrogen Bond Donors 5
Hydrogen Bond Acceptors 6
logP 4.86
Molar Refractivity 140.20

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