Contents

Leukotriene C₄

Leukotriene C₄

Names
Systematic IUPAC name (5S,6R,7E,9E,11Z,14Z)-6-({(2R)-2-[(4S)-4-Amino-4-carboxybutanamido]-3-[(carboxymethyl)amino]-3-oxopropyl}sulfanyl)-5-hydroxyicosa-7,9,11,14-tetraenoic acid
Identifiers
CAS Number	72025-60-6 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16978 Y
ChemSpider	4444133 N
ECHA InfoCard	100.212.805
EC Number	200-659-6
KEGG	C02166 Y
MeSH	Leukotriene+C4
PubChem CID	5280493
UNII	2CU6TT9V48 Y
CompTox Dashboard (EPA)	DTXSID00903946
InChI 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 N Key: GWNVDXQDILPJIG-NXOLIXFESA-N N InChI=1/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 Key: GWNVDXQDILPJIG-NXOLIXFEBR
SMILES CCCCC/C=C\C/C=C\C=C\C=C\[C@H]([C@H](CCCC(=O)O)O)SC[C@@H](/C(=N/CC(=O)O)/O)/N=C(\CC[C@@H](C(=O)O)N)/O
Properties
Chemical formula	C30H47N3O9S
Molar mass	625.78 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Chemical compound

Leukotriene C₄ (LTC₄) is a leukotriene. LTC₄ has been extensively studied in the context of allergy and asthma.^[1][2] In cells of myeloid origin such as mast cells, its biosynthesis is orchestrated by translocation to the nuclear envelope along with co-localization of cytosolic phospholipase A2 (cPLA2), arachidonate 5-lipoxygenase (5-LO), 5-lipoxygenase-activating protein (FLAP) and LTC₄ synthase (LTC₄S), which couples glutathione to an LTA₄ intermediate. The MRP1 transporter then secretes cytosolic LTC₄ and cell surface proteases further metabolize it by sequential cleavage of the γ-glutamyl and glycine residues off its glutathione segment, generating the more stable products LTD₄ and LTE₄. All three leukotrienes then bind at different affinities to two G-protein coupled receptors: CYSLTR1 and CYSLTR2, triggering pulmonary vasoconstriction and bronchoconstriction.^[3]

In cells of non-haematopoietic lineage, endoplasmic reticulum (ER) stress and chemotherapy induce LTC₄ biosynthesis by transcriptionally upregulating and activating the enzyme microsomal glutathione-S-transferase 2 (MGST2). ER stress and chemotherapy also trigger nuclear translocation of the two LTC₄ receptors. Acting in an intracrine manner, LTC₄ then elicits nuclear translocation of NADPH oxidase 4 (NOX4), ROS accumulation and oxidative DNA damage.^[4] Besides being a potent lipid mediator in asthma and inflammation, LTC₄ was reported to be involved in several other diseases, such as allergic airway diseases, dermatological diseases, cardiovascular diseases, liver injury, atherosclerosis and colon cancer.^[5][6][7]