Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:09:46 UTC
Update Date2022-03-07 02:51:27 UTC
HMDB IDHMDB0012914
Secondary Accession Numbers
  • HMDB12914
Metabolite Identification
Common NameCoA-omega-COOH-dinor-LTE4
DescriptionCoA-omega-COOH-dinor-LTE4 is a metabolite through lipid oxidation of Leukotriene E4 (LTE4).Leukotriene E4 (LTE4) is a cysteinyl leukotriene. Cysteinyl leukotrienes (CysLTs) are a family of potent inflammatory mediators that appear to contribute to the pathophysiologic features of allergic rhinitis. Nasal blockage induced by CysLTs is mainly due to dilatation of nasal blood vessels, which can be induced by the nitric oxide produced through CysLT1 receptor activation. LTE4, activate contractile and inflammatory processes via specific interaction with putative seven transmembrane-spanning receptors that couple to G proteins and subsequent intracellular signaling pathways. LTE4 is metabolized from leukotriene C4 in a reaction catalyzed by gamma-glutamyl transpeptidase and a particulate dipeptidase from kidney. (PMID: 12607939 , 12432945 , 6311078 ). 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?1582753077
Synonyms
ValueSource
Linoleoyl-coenzyme AHMDB
6-[(2-Amino-2-carboxyethyl)sulfanyl]-18-({2-[(3-{[4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulfanyl)-5-hydroxy-18-oxooctadeca-7,9,11,14-tetraenoateHMDB
6-[(2-Amino-2-carboxyethyl)sulphanyl]-18-({2-[(3-{[4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulphanyl)-5-hydroxy-18-oxooctadeca-7,9,11,14-tetraenoateHMDB
6-[(2-Amino-2-carboxyethyl)sulphanyl]-18-({2-[(3-{[4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,2-dihydroxy-3,3-dimethylbutylidene]amino}-1-hydroxypropylidene)amino]ethyl}sulphanyl)-5-hydroxy-18-oxooctadeca-7,9,11,14-tetraenoic acidHMDB
Chemical FormulaC42H65N8O22P3S2
Average Molecular Weight1191.06
Monoisotopic Molecular Weight1190.286769107
IUPAC Name6-[(2-amino-2-carboxyethyl)sulfanyl]-18-{[2-(3-{3-[({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-5-hydroxy-18-oxooctadeca-7,9,11,14-tetraenoic acid
Traditional Name6-[(2-amino-2-carboxyethyl)sulfanyl]-18-({2-[3-(3-{[({[5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-5-hydroxy-18-oxooctadeca-7,9,11,14-tetraenoic acid
CAS Registry NumberNot Available
SMILES
CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(O)C(=O)NCCC(=O)NCCSC(=O)CCC=CCC=CC=CC=CC(SCC(N)C(O)=O)C(O)CCCC(O)=O
InChI Identifier
InChI=1S/C42H65N8O22P3S2/c1-42(2,23-69-75(66,67)72-74(64,65)68-21-28-35(71-73(61,62)63)34(56)40(70-28)50-25-49-33-37(44)47-24-48-38(33)50)36(57)39(58)46-18-17-30(52)45-19-20-76-32(55)16-11-9-7-5-3-4-6-8-10-14-29(77-22-26(43)41(59)60)27(51)13-12-15-31(53)54/h3-4,6-10,14,24-29,34-36,40,51,56-57H,5,11-13,15-23,43H2,1-2H3,(H,45,52)(H,46,58)(H,53,54)(H,59,60)(H,64,65)(H,66,67)(H2,44,47,48)(H2,61,62,63)
InChI KeyQFIFJHIRXMCJMO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentLong-chain fatty acyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Octadecanoid
  • Long-chain fatty acid
  • Cysteine or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Hydroxy fatty acid
  • Monoalkyl phosphate
  • Thia fatty acid
  • Fatty acid
  • Imidolactam
  • Dicarboxylic acid or derivatives
  • Alkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Unsaturated fatty acid
  • Phosphoric acid ester
  • Pyrimidine
  • Imidazole
  • Oxolane
  • Azole
  • Heteroaromatic compound
  • Amino acid
  • Secondary alcohol
  • Thiocarboxylic acid ester
  • Carbothioic s-ester
  • Amino acid or derivatives
  • Dialkylthioether
  • Sulfenyl compound
  • Oxacycle
  • Thioether
  • Carboximidic acid
  • Azacycle
  • Thiocarboxylic acid or derivatives
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Primary aliphatic amine
  • Primary amine
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organosulfur compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
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
PropertyValueSource
Water Solubility0.92 g/LALOGPS
logP1.15ALOGPS
logP-4.6ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)0.81ChemAxon
pKa (Strongest Basic)9.13ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count23ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area484.48 ŲChemAxon
Rotatable Bond Count37ChemAxon
Refractivity279.65 m³·mol⁻¹ChemAxon
Polarizability115.06 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+317.11330932474
DeepCCS[M-H]-315.21730932474
DeepCCS[M-2H]-349.08730932474
DeepCCS[M+Na]+323.10230932474
AllCCS[M+H]+322.032859911
AllCCS[M+H-H2O]+322.832859911
AllCCS[M+NH4]+321.232859911
AllCCS[M+Na]+320.932859911
AllCCS[M-H]-308.532859911
AllCCS[M+Na-2H]-313.932859911
AllCCS[M+HCOO]-319.832859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CoA-omega-COOH-dinor-LTE4 10V, Positive-QTOFsplash10-000i-1900010000-3135169a1c613b6da3572019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CoA-omega-COOH-dinor-LTE4 20V, Positive-QTOFsplash10-000i-0900223000-c34a5f83c51dba8d9b272019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CoA-omega-COOH-dinor-LTE4 40V, Positive-QTOFsplash10-000i-1900101000-8d3f7ebb553e27cdff612019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CoA-omega-COOH-dinor-LTE4 10V, Negative-QTOFsplash10-0089-2900121200-b5b7037e246ae633fa672019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CoA-omega-COOH-dinor-LTE4 20V, Negative-QTOFsplash10-001i-4900110000-85dc377a7f7688f533d22019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CoA-omega-COOH-dinor-LTE4 40V, Negative-QTOFsplash10-057r-6900100000-2800ab6b6da497cd33fa2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CoA-omega-COOH-dinor-LTE4 10V, Negative-QTOFsplash10-0019-3900000000-50089ca60b1ab0c141132021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CoA-omega-COOH-dinor-LTE4 20V, Negative-QTOFsplash10-001i-9100000001-efe53501b5f113c77be02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CoA-omega-COOH-dinor-LTE4 40V, Negative-QTOFsplash10-0036-9001200000-747233a6bbddf0aa181b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CoA-omega-COOH-dinor-LTE4 10V, Positive-QTOFsplash10-0udi-9400000003-2dff6a3c296872834ae62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CoA-omega-COOH-dinor-LTE4 20V, Positive-QTOFsplash10-000i-5900000003-862760a0f1232aa5eda62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CoA-omega-COOH-dinor-LTE4 40V, Positive-QTOFsplash10-001i-1410509000-e354e3b65c2e72583f042021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029205
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound76043818
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mizutani N: [Studies on the experimental allergic rhinitis induced by Japanese cedar pollen--role of cysteinyl leukotrienes in nasal allergic symptoms]. Yakugaku Zasshi. 2003 Jan;123(1):1-8. [PubMed:12607939 ]
  2. Evans JF: Cysteinyl leukotriene receptors. Prostaglandins Other Lipid Mediat. 2002 Aug;68-69:587-97. [PubMed:12432945 ]
  3. Hammarstrom S: Leukotrienes. Annu Rev Biochem. 1983;52:355-77. [PubMed:6311078 ]
  4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  5. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  6. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.