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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-10-25 12:27:12 UTC
Update Date2022-03-07 02:49:25 UTC
HMDB IDHMDB0005085
Secondary Accession Numbers
  • HMDB05085
Metabolite Identification
Common NameLeukotriene B4 dimethylamide
DescriptionLeukotriene 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 , 17623009 )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?1582752344
Synonyms
ValueSource
LTB4 Dimethyl amideHMDB
LTB4-DimethylamideHMDB
N,N-Dimethyl-5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraen-1-amideHMDB
[S-[R*,s*-(e,Z,e,Z)]]-5,12-dihydroxy-N,N-dimethyl-6,8,10,14-eicosatetraenamideHMDB
LTB4dMAHMDB
Leukotriene b4 dimethylamideMeSH
Chemical FormulaC22H37NO3
Average Molecular Weight363.5341
Monoisotopic Molecular Weight363.277344055
IUPAC Name(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxy-N,N-dimethylicosa-6,8,10,14-tetraenamide
Traditional NameLTB4-dimethylamide
CAS Registry Number83024-92-4
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 KeyBBJRTSLPWQUASB-UKODYPNASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty amides
Direct ParentN-acyl amines
Alternative Parents
Substituents
  • N-acyl-amine
  • Tertiary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.493Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP4.84ALOGPS
logP3.77ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)17.72ChemAxon
pKa (Strongest Basic)-0.18ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area60.77 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity114.6 m³·mol⁻¹ChemAxon
Polarizability43.72 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+200.70931661259
DarkChem[M-H]-194.3431661259
DeepCCS[M+H]+201.12230932474
DeepCCS[M-H]-198.72630932474
DeepCCS[M-2H]-232.48330932474
DeepCCS[M+Na]+207.62630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Leukotriene B4 dimethylamideCCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(=O)N(C)C4068.3Standard polar33892256
Leukotriene B4 dimethylamideCCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(=O)N(C)C2912.6Standard non polar33892256
Leukotriene B4 dimethylamideCCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(=O)N(C)C3150.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Leukotriene B4 dimethylamide,1TMS,isomer #1CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)N(C)C)O[Si](C)(C)C3101.4Semi standard non polar33892256
Leukotriene B4 dimethylamide,1TMS,isomer #2CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)N(C)C)O[Si](C)(C)C3114.4Semi standard non polar33892256
Leukotriene B4 dimethylamide,2TMS,isomer #1CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)N(C)C)O[Si](C)(C)C)O[Si](C)(C)C3136.5Semi standard non polar33892256
Leukotriene B4 dimethylamide,1TBDMS,isomer #1CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)N(C)C)O[Si](C)(C)C(C)(C)C3362.2Semi standard non polar33892256
Leukotriene B4 dimethylamide,1TBDMS,isomer #2CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)N(C)C)O[Si](C)(C)C(C)(C)C3368.5Semi standard non polar33892256
Leukotriene B4 dimethylamide,2TBDMS,isomer #1CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)N(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3633.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Leukotriene B4 dimethylamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-6579000000-8c934e9462d2d7c37ac62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Leukotriene B4 dimethylamide GC-MS (2 TMS) - 70eV, Positivesplash10-0006-9102600000-ee229477075ad47100742017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Leukotriene B4 dimethylamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 dimethylamide 10V, Positive-QTOFsplash10-01ot-0009000000-998e72a31c13593784012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 dimethylamide 20V, Positive-QTOFsplash10-0gxt-5679000000-527bebcda5b12fba53f62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 dimethylamide 40V, Positive-QTOFsplash10-000f-9530000000-88c8cb32eeb9889740402017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 dimethylamide 10V, Negative-QTOFsplash10-03di-0009000000-8fb4339f3468eb35a70f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 dimethylamide 20V, Negative-QTOFsplash10-03xu-1129000000-0e3ae91fe1d964d014982017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 dimethylamide 40V, Negative-QTOFsplash10-00di-9241000000-5f90e31e4be94fdd9bfb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 dimethylamide 10V, Negative-QTOFsplash10-03di-0009000000-5845818a3db0506615282021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 dimethylamide 20V, Negative-QTOFsplash10-03dl-1239000000-ec456dee5f30473017262021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 dimethylamide 40V, Negative-QTOFsplash10-007c-9274000000-1631deb55769407a4d342021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 dimethylamide 10V, Positive-QTOFsplash10-002b-0119000000-33de9f29a7c0db4ef9632021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 dimethylamide 20V, Positive-QTOFsplash10-0fba-3229000000-3b7b404fcc3d15cfd8042021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 dimethylamide 40V, Positive-QTOFsplash10-0aos-9220000000-d48f0f349576a05fc4e02021-09-24Wishart 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 IDFDB023624
KNApSAcK IDNot Available
Chemspider ID4446250
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283126
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. 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 ]
  2. Murphy RC, Gijon MA: Biosynthesis and metabolism of leukotrienes. Biochem J. 2007 Aug 1;405(3):379-95. [PubMed:17623009 ]
  3. Lipid Maps (LMFA03020011) [Link]