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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 14:59:13 UTC
HMDB IDHMDB0001198
Secondary Accession Numbers
  • HMDB0006015
  • HMDB01198
  • HMDB06015
Metabolite Identification
Common NameLeukotriene C4
DescriptionLeukotriene C4 (LTC4) is a cysteinyl leukotriene (CysLT), a family of potent inflammatory mediators. Eosinophils, one of the principal cell types recruited to and activated at sites of allergic inflammation, is capable of elaborating lipid mediators, including leukotrienes derived from the oxidative metabolism of arachidonic acid (AA). Potentially activated eosinophils may elaborate greater quantities of LTC4, than normal eosinophils. These activated eosinophils thus are primed for enhanced LTC4 generation in response to subsequent stimuli. Some recognized priming stimuli are chemoattractants (e.g. eotaxin, PAF) that may participate in the recruitment of eosinophils to sites of allergic inflammation. The mechanisms by which chemoattractants and other activating cytokines (e.g. interleukin (IL)-5) or extracellular matrix components (e.g. fibronectin) enhance eosinophil eicosanoid formation are pertinent to the functions of these eicosanoids as paracrine mediators of allergic inflammation. Some eosinophil-derived eicosanoids may be active in down-regulating inflammation. It is increasingly likely that eicosanoids synthesized within cells, including eosinophils, may have intracellular (e.g. intracrine) roles in regulating cell functions, in addition to the more recognized activities of eicosanoids as paracrine mediators of inflammation. Acting extracellularly, the cysteinyl leukotrienes (CysLTs) LTC4 and its extracellular derivatives, LTD4 and LTE4 are key paracrine mediators pertinent to asthma and allergic diseases. Based on their receptor-mediated capabilities, they can elicit bronchoconstriction, mucus hypersecretion, bronchial hyperresponsiveness, increased microvascular permeability, and additional eosinophil infiltration. Eosinophils are a major source of CysLTs and have been identified as the principal LTC4 synthase expressing cells in bronchial mucosal biopsies of asthmatic subjects (PMID: 12895596 ). Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways.
Structure
Thumb
Synonyms
Chemical FormulaC30H47N3O9S
Average Molecular Weight625.774
Monoisotopic Molecular Weight625.303300807
IUPAC Name(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid
Traditional Nameleukotriene C4
CAS Registry Number72025-60-6
SMILES
CCCCC\C=C/C\C=C/C=C/C=C/[C@@H](SC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O)[C@@H](O)CCCC(O)=O
InChI Identifier
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
InChI KeyGWNVDXQDILPJIG-NXOLIXFESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Gamma-glutamyl alpha peptide
  • Leukotriene
  • Hydroxyeicosatetraenoic acid
  • Eicosanoid
  • Glutamine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Cysteine or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Alpha-amino acid
  • N-substituted-alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Hydroxy fatty acid
  • Thia fatty acid
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Secondary alcohol
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Dialkylthioether
  • Carboxylic acid
  • Sulfenyl compound
  • Thioether
  • Primary amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Naturally occurring process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Locations
  • Epidermis
  • Eye Lens
  • Intestine
  • Leukocyte
  • Platelet
  • Smooth Muscle
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Eczema
  1. Hua Z, Fei H, Mingming X: Evaluation and interference of serum and skin lesion levels of leukotrienes in patients with eczema. Prostaglandins Leukot Essent Fatty Acids. 2006 Jul;75(1):51-5. Epub 2006 Jun 6. [PubMed:16757158 ]
Leukotriene C4-Synthesis Deficiency
  1. Mayatepek E, Flock B: Leukotriene C4-synthesis deficiency: a new inborn error of metabolism linked to a fatal developmental syndrome. Lancet. 1998 Nov 7;352(9139):1514-7. [PubMed:9820300 ]
AIDS
  1. Froldi M, Castagna A, Parma M, Piona A, Tedeschi A, Miadonna A, Lorini M, Orazio EN, Lazzarin A: Mediator release in cerebrospinal fluid of human immunodeficiency virus-positive patients with central nervous system involvement. J Neuroimmunol. 1992 May;38(1-2):155-61. [PubMed:1315794 ]
Aseptic meningitis
  1. Matsuo M, Hamasaki Y, Masuyama T, Ohta M, Miyazaki S: Leukotriene B4 and C4 in cerebrospinal fluid from children with meningitis and febrile seizures. Pediatr Neurol. 1996 Feb;14(2):121-4. [PubMed:8703223 ]
Glutathione synthetase deficiency
  1. Mayatepek E, Meissner T, Grobe H: Acute metabolic crisis with extreme deficiency of glutathione in combination with decreased levels of leukotriene C4 in a patient with glutathione synthetase deficiency. J Inherit Metab Dis. 2004;27(2):297-9. [PubMed:15243994 ]
Hydrocephalus
  1. Westcott JY, Murphy RC, Stenmark K: Eicosanoids in human ventricular cerebrospinal fluid following severe brain injury. Prostaglandins. 1987 Dec;34(6):877-87. [PubMed:2835791 ]
Associated OMIM IDs
DrugBank IDDB08855
Phenol Explorer Compound IDNot Available
FooDB IDFDB030979
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC02166
BioCyc IDLEUKOTRIENE-C4
BiGG IDNot Available
Wikipedia LinkLeukotriene_C4
METLIN IDNot Available
PubChem Compound5280493
PDB IDNot Available
ChEBI ID16978
Food Biomarker OntologyNot Available
VMH IDLEUKTRC4
MarkerDB IDMDB00000307
Good Scents IDNot Available
References
Synthesis ReferenceRokach, Joshua; Young, Robert N.; Kakushima, Masatoshi; Lau, Cheuk-Kun; Seguin, Rick; Frenette, Richard; Guindon, Yvan. Synthesis of leukotrienes. New synthesis of natural leukotriene A4. Tetrahedron Letters (1981), 22(11), 979-82.
Material Safety Data Sheet (MSDS)Not Available
General References

Enzymes

General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Initiates extracellular glutathione (GSH) breakdown, provides cells with a local cysteine supply and contributes to maintain intracellular GSH level. It is part of the cell antioxidant defense mechanism. Catalyzes the transfer of the glutamyl moiety of glutathione to amino acids and dipeptide acceptors. Alternatively, glutathione can be hydrolyzed to give Cys-Gly and gamma glutamate. Isoform 3 seems to be inactive.
Gene Name:
GGT1
Uniprot ID:
P19440
Molecular weight:
61409.67
Reactions
Leukotriene C4 + Amino acid → Leukotriene D4 + 5-L-Glutamyl amino aciddetails
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves glutathione conjugates (By similarity).
Gene Name:
GGT7
Uniprot ID:
Q9UJ14
Molecular weight:
70466.015
Reactions
Leukotriene C4 + Amino acid → Leukotriene D4 + 5-L-Glutamyl amino aciddetails
General function:
Involved in enzyme activator activity
Specific function:
Catalyzes the conjugation of leukotriene A4 with reduced glutathione to form leukotriene C4.
Gene Name:
LTC4S
Uniprot ID:
Q16873
Molecular weight:
16566.465
Reactions
Leukotriene A4 + Glutathione → Leukotriene C4details
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves glutathione conjugates (By similarity).
Gene Name:
GGT6
Uniprot ID:
Q6P531
Molecular weight:
50508.83
Reactions
Leukotriene C4 + Amino acid → Leukotriene D4 + 5-L-Glutamyl amino aciddetails
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Not Available
Gene Name:
GGT7
Uniprot ID:
A0PJJ9
Molecular weight:
62565.3
General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Cleaves the gamma-glutamyl peptide bond of glutathione conjugates, but maybe not glutathione itself. Converts leukotriene C4 (LTC4) to leukotriene D4 (LTD4).
Gene Name:
GGT5
Uniprot ID:
P36269
Molecular weight:
62331.75
Reactions
Leukotriene C4 + Amino acid → Leukotriene D4 + 5-L-Glutamyl amino aciddetails

Transporters

General function:
Involved in ATP binding
Specific function:
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o- glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency
Gene Name:
ABCC1
Uniprot ID:
P33527
Molecular weight:
171589.5