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Human Metabolome Database Version 3.5

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Showing metabocard for CoA-20-COOH-LTE4 (HMDB12913)

Record Information
Version 3.5
Creation Date 2009-07-24 18:09:45 -0600
Update Date 2013-02-08 17:29:32 -0700
HMDB ID HMDB12913
Secondary Accession Numbers None
Metabolite Identification
Common Name CoA-20-COOH-LTE4
Description CoA-20-COOH-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 Link_out, 12432945 Link_out, 6311078 Link_out). 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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Linoleoyl-coenzyme a
Chemical Formula C44H65N8O22P3S2
Average Molecular Weight 1215.079
Monoisotopic Molecular Weight 1214.28676672
IUPAC Name 3-({2-[(2-{[(6E,9E,11E,13E,15R,16S)-15-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-19-carboxy-16-hydroxynonadeca-6,9,11,13-tetraenoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-3-hydroxy-2,2-dimethylpropyl ({[(2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphonate
Traditional IUPAC Name 3-({2-[(2-{[(6E,9E,11E,13E,15R,16S)-15-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-19-carboxy-16-hydroxynonadeca-6,9,11,13-tetraenoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-3-hydroxy-2,2-dimethylpropyl {[(2R,3R,4S,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(pho
CAS Registry Number Not Available
SMILES O[C@@H](CCCC(O)=O)[C@H](SC[C@@H](N)C(O)=O)\C=C\C=C\C=C\C\C=C\CCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@@H](O)[C@H]1OP([O-])([O-])=O)N1C=NC2=C1N=CN=C2N
InChI Identifier InChI=1S/C44H69N8O22P3S2/c1-44(2,25-71-77(68,69)74-76(66,67)70-23-30-37(73-75(63,64)65)36(58)42(72-30)52-27-51-35-39(46)49-26-50-40(35)52)38(59)41(60)48-20-19-32(54)47-21-22-78-34(57)18-13-11-9-7-5-3-4-6-8-10-12-16-31(79-24-28(45)43(61)62)29(53)15-14-17-33(55)56/h4-8,10,12,16,26-31,36-38,42,53,58-59H,3,9,11,13-15,17-25,45H2,1-2H3,(H,47,54)(H,48,60)(H,55,56)(H,61,62)(H,66,67)(H,68,69)(H2,46,49,50)(H2,63,64,65)/p-4/b6-4+,7-5+,10-8+,16-12+/t28-,29+,30-,31-,36+,37+,38?,42-/m1/s1
InChI Key KONKGRIDBYMNKG-VSGWDHNFSA-J
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class Acyl CoAs
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Organic Compounds
  • Unsaturated Fatty Acids
Substituents
  • 1 Phosphoribosyl Imidazole
  • Alpha Amino Acid Or Derivative
  • Carboxamide Group
  • Carboxylic Acid Salt
  • Carboxylic Thioester
  • Coenzyme A
  • Dicarboxylic Acid Derivative
  • Glyco Amino Acid
  • Glycosyl Compound
  • Hydroxyeicosapolyenoic Acid
  • Imidazole
  • Imidazopyrimidine
  • Leukotriene
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Primary Aliphatic Amine (Alkylamine)
  • Purine
  • Purine Ribonucleoside Diphosphate
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Thiocarboxylic Acid Ester
  • Thioether
Direct Parent Acyl CoAs
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.52 g/L ALOGPS
LogP 0.62 ALOGPS
LogP -4.8 ChemAxon
LogS -3.40 ALOGPS
pKa (strongest acidic) 0.81 ChemAxon
pKa (strongest basic) 9.13 ChemAxon
Hydrogen Acceptor Count 23 ChemAxon
Hydrogen Donor Count 9 ChemAxon
Polar Surface Area 495.8 A2 ChemAxon
Rotatable Bond Count 39 ChemAxon
Refractivity 284.36 ChemAxon
Polarizability 117.23 ChemAxon
Formal Charge -4 ChemAxon
Physiological Charge -5 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB029204
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB12913 Link_out
Metagene Link HMDB12913 Link_out
METLIN ID Not Available
PubChem Compound 53481544 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available