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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-10-25 14:18:43 UTC
Update Date2020-02-26 21:25:45 UTC
HMDB IDHMDB0005095
Secondary Accession Numbers
  • HMDB05095
Metabolite Identification
Common Name11-trans-Leukotriene C4
Description11-trans-Leukotriene C4 (11-trans-LTC4) is a leukotriene derivative formed by the metabolism of LTA4 and is found in human endothelial cells. Leukotrienes (LT) are a family of naturally occurring lipids that are oxygenated metabolites of arachidonic acid. Biosynthesis of the leukotrienes involves the action of a lipoxygenase on arachidonate to yield a hydroperoxy intermediate which is then dehydrated to the allylic epoxide, LTA4. LTA4 can be hydrolyzed to the dihydroxy acid, LTB4 or it can be conjugated with glutathione (GSH) to produce the parent slow reacting substance, LTC4. The leukotrienes are mediators of inflammation, hypersensitivity reactions, and respiratory disorders. On a cellular level, LTC4 and its metabolites, LTD4 and LTE4, are potent constrictors of vascular bronchial smooth muscle. LTC4 and LTD4 also induce plasma leakage from the microvasculature. LTB4 is a potent polymorphonuclear leukocyte (PMNL) chemotaxin and induces neutrophils to degranulate, generate superoxide, and adhere to vascular endothelium. Several investigations of leukotriene synthesis by blood vessels and cultured vascular cells have been undertaken. Vascular preparations have been shown to produce LTB4 and LTC4 and to metabolize LTC4 to LTD4 and LTE4. In addition, mast cells, macrophages, and PMNL, all of which may contaminate whole vessel preparations, are known to synthesize both peptide-containing and dihydroxy acid leukotrienes. Consequently, it is unclear what cells are contributing to vascular leukotriene synthesis. No evidence of isolated vascular cell leukotriene synthesis is currently available. Indeed, this report and others have been unable to detect endothelial cell conversion of arachidonic acid to the leukotrienes. The fact that vascular endothelium lacks the full complement of leukotriene biosynthetic enzymes does not preclude an active role for this tissue in leukotriene metabolism. In some cases, tissues which are not known to synthesize leukotrienes from arachidonate are able to catalyze one or more of the intermediate steps of the pathway. In the present investigation, the leukotriene metabolism of porcine aortic endothelium has been studied. Evidence is presented which indicates that endothelial cells are unable to convert arachidonic acid to LTC4 but, nevertheless, contain LTC4 synthetase. Additional experiments suggest that a neutrophil-endothelial cell interaction augments vascular LTC4 synthesis by the intercellular transfer of LTA4 from PMNL to endothelial cells (PMID: 3023351 ). 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
Data?1582752345
Synonyms
ValueSource
11-trans-LTC4HMDB
5S-Hydroxy-6R-(S-glutathionyl)-7E,9E,11E14Z-eicosatetraenoateHMDB
5S-Hydroxy-6R-(S-glutathionyl)-7E,9E,11E14Z-eicosatetraenoic acidHMDB
Leukotriene C2HMDB
[R-[R*,s*-(e,e,e,Z)]]-N-[S-[1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl]-N-L-g-glutamyl-L-cysteinyl]-glycineHMDB
[R-[R*,s*-(e,e,e,Z)]]-N-[S-[1-(4-carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl]-N-L-gamma-glutamyl-L-cysteinyl]-glycineHMDB
5(S)-Hydroxy-6(R)-S-glutathionyl-7,9,11-trans-14-cis-eicosatetraenoic acidHMDB
Leukotriene C-2HMDB
11-trans LeukotrieneHMDB
Leukotriene CMeSH
Leukotriene C 1MeSH
Leukotriene C 4MeSH
Leukotriene C-1MeSH
Leukotrienes CMeSH
LTC4MeSH
Leukotriene C4MeSH
Leukotriene C1MeSH
Leukotriene C-4MeSH
Chemical FormulaC30H47N3O9S
Average Molecular Weight625.774
Monoisotopic Molecular Weight625.303300807
IUPAC Name(5S,6R,7E,9E,11E,14Z)-6-{[(2R)-2-[(4S)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid
Traditional Name11-trans-LTC4
CAS Registry Number74841-69-3
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-CCHJCNDSSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as thromboxanes. These are eicosanoids structurally characterized by the presence of a 6-member ether containing ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentThromboxanes
Alternative Parents
Substituents
  • Thromboxane
  • Long-chain fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Oxane
  • Unsaturated fatty acid
  • Hemiacetal
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.571Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0025 g/LALOGPS
logP0.04ALOGPS
logP-0.015ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)1.8ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area216.35 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity168.51 m³·mol⁻¹ChemAxon
Polarizability69.08 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05o0-3202091000-c6dee8507ab8b61b0c02Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0zml-4302049000-ebdf4a1bf7a63bddbe22Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00di-0000009000-9ba4d29fb234bf629c19Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00di-0000009000-c2e3b5fb18c749bec683Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00di-0000009000-764950659a3ede43e5faSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00di-0000009000-84d0f40152dc35593991Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00di-0000009000-2b9de1e9017bddef56ffSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00di-0020019000-c37ade6bbbbb0db63082Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0c00-0290044000-556a3c7aef20c3fd1ba2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0un9-0492001000-2801dff9e15f1a96421cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-01t9-0970000000-e6b8d4063abe84fe54f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0bwc-1011195000-27df91ea69a303a3b692Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-7403490000-a761a2807aa7a3cb8f28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9547230000-ffbfa2fdb737a3d1d7d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pir-0116059000-63fb8e625f40ffbca3d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kai-0139110000-287fbebe3e5ea0115fa5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0h2b-2913000000-0b8b08aa7450d274f719Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000009 +/- 0.000002 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023628
KNApSAcK IDNot Available
Chemspider ID4446258
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLeukotriene C4
METLIN IDNot Available
PubChem Compound5283134
PDB IDNot Available
ChEBI ID607671
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Feinmark SJ, Cannon PJ: Endothelial cell leukotriene C4 synthesis results from intercellular transfer of leukotriene A4 synthesized by polymorphonuclear leukocytes. J Biol Chem. 1986 Dec 15;261(35):16466-72. [PubMed:3023351 ]
  2. Lipid Maps (LMFA03020020) [Link]