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Human Metabolome Database Version 3.5

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Showing metabocard for 18E-20-oxo-20-CoA-LTB4 (HMDB12609)

Record Information
Version 3.5
Creation Date 2009-07-24 18:03:52 -0600
Update Date 2013-02-08 17:29:23 -0700
HMDB ID HMDB12609
Secondary Accession Numbers None
Metabolite Identification
Common Name 18E-20-oxo-20-CoA-LTB4
Description 18E-20-oxo-20-CoA-LTB4 is formed when leukotriene B4 (LTB4) is metabolized by beta-oxidation. LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. (PMID: 8632343 Link_out, 9667737 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. CoA-20-COOH-19E-LTB(,4)
  2. Coenzyme A-20-COOH-19E-LTB(,4)
Chemical Formula C41H58N7O21P3S
Average Molecular Weight 1109.92
Monoisotopic Molecular Weight 1109.261932179
IUPAC Name 3-({2-[(2-{[(2E,6Z,9S,10E,12E,14Z,16R)-19-carboxy-9,16-dihydroxynonadeca-2,6,10,12,14-pentaenoyl]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-{[(2E,6Z,9S,10E,12E,14Z,16R)-19-carboxy-9,16-dihydroxynonadeca-2,6,10,12,14-pentaenoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-3-hydroxy-2,2-dimethylpropyl {[(2R,3R,4S,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl ph
CAS Registry Number Not Available
SMILES O[C@H](CCCC(O)=O)\C=C/C=C/C=C/[C@@H](O)C\C=C/CC\C=C\C(=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/C41H62N7O21P3S/c1-41(2,24-66-72(63,64)69-71(61,62)65-23-29-35(68-70(58,59)60)34(55)40(67-29)48-26-47-33-37(42)45-25-46-38(33)48)36(56)39(57)44-20-19-30(51)43-21-22-73-32(54)18-11-5-3-4-8-13-27(49)14-9-6-7-10-15-28(50)16-12-17-31(52)53/h4,6-11,14-15,18,25-29,34-36,40,49-50,55-56H,3,5,12-13,16-17,19-24H2,1-2H3,(H,43,51)(H,44,57)(H,52,53)(H,61,62)(H,63,64)(H2,42,45,46)(H2,58,59,60)/p-4/b7-6+,8-4-,14-9+,15-10-,18-11+/t27-,28-,29+,34-,35-,36?,40+/m0/s1
InChI Key PBPMTFAECBJRFW-KBPAAJSHSA-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
  • Allyl Alcohol
  • Carboxamide Group
  • Carboxylic Acid Salt
  • Carboxylic Thioester
  • Coenzyme A
  • Enone
  • Glycosyl Compound
  • Hydroxyeicosapolyenoic Acid
  • Imidazole
  • Imidazopyrimidine
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Purine
  • Purine Ribonucleoside Diphosphate
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Thiocarboxylic Acid Ester
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 0.62 g/L ALOGPS
LogP 1.96 ALOGPS
LogP -3.7 ChemAxon
LogS -3.28 ALOGPS
pKa (strongest acidic) 0.83 ChemAxon
pKa (strongest basic) 5.1 ChemAxon
Hydrogen Acceptor Count 21 ChemAxon
Hydrogen Donor Count 8 ChemAxon
Polar Surface Area 452.71 A2 ChemAxon
Rotatable Bond Count 34 ChemAxon
Refractivity 260.82 ChemAxon
Polarizability 105.17 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 FDB029147
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 HMDB12609 Link_out
Metagene Link HMDB12609 Link_out
METLIN ID Not Available
PubChem Compound 53481492 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