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Showing Compound 16,18-Oxo-18-CoA-dinor-LTE4 (FDB029139)

Record Information
Version1.0
Creation date2011-09-21 01:50:41 UTC
Update date2015-07-21 06:59:38 UTC
Primary IDFDB029139
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name16,18-Oxo-18-CoA-dinor-LTE4
Description16,18-oxo-18-CoA-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 signaling pathways. [HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility1.84 g/LALOGPS
logP0ALOGPS
logP-6ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)0.81ChemAxon
pKa (Strongest Basic)9.13ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area512.87 ŲChemAxon
Rotatable Bond Count38ChemAxon
Refractivity274.74 m³·mol⁻¹ChemAxon
Polarizability113.88 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC42H61N8O23P3S2
IUPAC name3-({2-[(2-{[(7Z,9E,11E,13R,14S)-13-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-17-carboxy-14-hydroxy-3-oxoheptadeca-7,9,11-trienoyl]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
InChI IdentifierInChI=1S/C42H65N8O23P3S2/c1-42(2,22-70-76(67,68)73-75(65,66)69-20-28-35(72-74(62,63)64)34(57)40(71-28)50-24-49-33-37(44)47-23-48-38(33)50)36(58)39(59)46-16-15-30(53)45-17-18-77-32(56)19-25(51)11-8-6-4-3-5-7-9-13-29(78-21-26(43)41(60)61)27(52)12-10-14-31(54)55/h3-5,7,9,13,23-24,26-29,34-36,40,52,57-58H,6,8,10-12,14-22,43H2,1-2H3,(H,45,53)(H,46,59)(H,54,55)(H,60,61)(H,65,66)(H,67,68)(H2,44,47,48)(H2,62,63,64)/p-4/b4-3-,7-5+,13-9+/t26-,27+,28-,29-,34+,35+,36?,40-/m1/s1
InChI KeyIPTNGKBINTWILB-MOGVCQQGSA-J
Isomeric SMILESO[C@@H](CCCC(O)=O)[C@H](SC[C@@H](N)C(O)=O)\C=C\C=C\C=C/CCCC(=O)CC(=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
Average Molecular Weight1203.025
Monoisotopic Molecular Weight1202.250381214
Classification
Description Belongs to the class of organic compounds known as long-chain 3-oxoacyl coas. These are organic compounds containing a coenzyme A derivative, which is 3-oxo acylated 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 3-oxoacyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • Ribonucleoside 3'-phosphate
  • Pentose-5-phosphate
  • Pentose phosphate
  • Long-chain fatty acid
  • Cysteine or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • Beta amino acid or derivatives
  • S-alkyl-l-cysteine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • 6-aminopurine
  • D-alpha-amino acid
  • Imidazopyrimidine
  • Purine
  • Hydroxy fatty acid
  • Thia fatty acid
  • Aminopyrimidine
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • Fatty acid
  • Imidolactam
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • 1,3-dicarbonyl compound
  • Unsaturated fatty acid
  • Pyrimidine
  • Tetrahydrofuran
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Thiocarboxylic acid ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carbothioic s-ester
  • Amino acid
  • Amino acid or derivatives
  • Ketone
  • Thiocarboxylic acid or derivatives
  • Thioether
  • Dialkylthioether
  • Carboxylic acid derivative
  • Sulfenyl compound
  • Carboxylic acid
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Primary amine
  • Carbonyl group
  • Organic nitrogen compound
  • Alcohol
  • Amine
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organosulfur compound
  • Organic anion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
SpectraNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53481480
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12594
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
No data available in table
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Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference