| Record Information |
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| Version | 1.0 |
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| Creation date | 2011-09-21 00:14:44 UTC |
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| Update date | 2015-07-21 06:57:14 UTC |
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| Primary ID | FDB022484 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Leukotriene C4 |
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| Description | Leukotriene 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, mucous 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 signaling pathways. [HMDB] |
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| CAS Number | 72025-60-6 |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C30H47N3O9S |
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| IUPAC name | (5S,6R)-6-{[(2R)-2-{[(4S)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid |
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| 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)/t22-,23-,24-,25+/m0/s1 |
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| InChI Key | GWNVDXQDILPJIG-OJJQZRKESA-N |
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| Isomeric SMILES | [H][C@](N)(CCC(=O)N[C@@]([H])(CS[C@]([H])(C=CC=CC=CCC=CCCCCC)[C@@]([H])(O)CCCC(O)=O)C(=O)NCC(O)=O)C(O)=O |
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| Average Molecular Weight | 625.774 |
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| Monoisotopic Molecular Weight | 625.303300807 |
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| Classification |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Amino acids, peptides, and analogues |
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| Direct Parent | Oligopeptides |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | |
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| Spectra |
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| Spectra | Not Available |
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| External Links |
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| ChemSpider ID | 4444133 |
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| ChEMBL ID | CHEMBL451509 |
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| KEGG Compound ID | C02166 |
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| Pubchem Compound ID | 5280493 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | 16978 |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB01198 |
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| CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | Not Available |
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| BIGG ID | 2212273 |
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| KNApSAcK ID | Not Available |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Leukotriene C4 |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | Not Available |
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| Enzymes | |
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| Pathways | |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | show |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | |
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