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Human Metabolome Database Version 3.5

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Showing metabocard for Leukotriene B4 dimethylamide (HMDB05085)

Record Information
Version 3.5
Creation Date 2006-10-25 06:27:12 -0600
Update Date 2013-02-08 17:13:53 -0700
HMDB ID HMDB05085
Secondary Accession Numbers None
Metabolite Identification
Common Name Leukotriene B4 dimethylamide
Description Leukotriene B4 dimethylamide is a derivative of Leukotriene B4 (LTB4) and was shown to inhibit neutrophil degranulation induced by LTB4. 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: 6288032 Link_out, 17623009 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. LTB4 dimethyl amide
  2. LTB4-dimethylamide
  3. N,N-Dimethyl-5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraen-1-amide
  4. [S-[R*,S*-(E,Z,E,Z)]]-5,12-dihydroxy-N,N-dimethyl-6,8,10,14-Eicosatetraenamide
Chemical Formula C22H37NO3
Average Molecular Weight 363.5341
Monoisotopic Molecular Weight 363.277344055
IUPAC Name (5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxy-N,N-dimethylicosa-6,8,10,14-tetraenamide
Traditional IUPAC Name LTB4 dimethyl amide
CAS Registry Number 83024-92-4
SMILES CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(=O)N(C)C
InChI Identifier InChI=1S/C22H37NO3/c1-4-5-6-7-8-11-15-20(24)16-12-9-10-13-17-21(25)18-14-19-22(26)23(2)3/h8-13,16-17,20-21,24-25H,4-7,14-15,18-19H2,1-3H3/b10-9+,11-8-,16-12+,17-13-/t20-,21-/m1/s1
InChI Key BBJRTSLPWQUASB-UKODYPNASA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Amides
Sub Class N-acyl Amines
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Acyclic Alkene
  • Allyl Alcohol
  • Carboxamide Group
  • Secondary Alcohol
  • Tertiary Carboxylic Acid Amide
Direct Parent N-acyl Amines
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 3.493 Not Available
Predicted Properties
Property Value Source
Water Solubility 0.012 g/L ALOGPS
LogP 4.84 ALOGPS
LogP 3.77 ChemAxon
LogS -4.47 ALOGPS
pKa (strongest acidic) 17.72 ChemAxon
pKa (strongest basic) -0.18 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 60.77 A2 ChemAxon
Rotatable Bond Count 14 ChemAxon
Refractivity 114.6 ChemAxon
Polarizability 43.72 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 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 FDB023624
KNApSAcK ID Not Available
Chemspider ID 4446250 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB05085 Link_out
Metagene Link HMDB05085 Link_out
METLIN ID Not Available
PubChem Compound 5283126 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Showell HJ, Otterness IG, Marfat A, Corey EJ: Inhibition of leukotriene B4-induced neutrophil degranulation by leukotriene B4-dimethylamide. Biochem Biophys Res Commun. 1982 Jun 15;106(3):741-7. Pubmed: 6288032 Link_out