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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-07-12 23:05:07 UTC
HMDB IDHMDB0001085
Secondary Accession Numbers
  • HMDB0005072
  • HMDB01085
  • HMDB05072
Metabolite Identification
Common NameLeukotriene B4
DescriptionLeukotriene B4 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 omega-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the omega-carboxy position and after CoA ester formation. Other specific pathways of leukotriene metabolism include the 12-hydroxydehydrogenase/15-oxo-prostaglandin-13-reductase that form a series of conjugated diene metabolites that have been observed to be excreted in human urine. Metabolism of LTC4 occurs by sequential peptide cleavage reactions involving a gamma-glutamyl transpeptidase that forms LTD4 (leukotriene D4) and a membrane-bound dipeptidase that converts LTD4 into LTE4 (leukotriene E4) before omega-oxidation. These metabolic transformations of the primary leukotrienes are critical for termination of their biological activity, and defects in expression of participating enzymes may be involved in specific genetic disease. The term leukotriene was coined to indicate the presence of three conjugated double bonds within the 20-carbon structure of arachidonic acid as well as the fact that these compounds were derived from leucocytes such as PMNNs or transformed mast cells. Interestingly, most of the cells known to express 5-LO are of myeloid origin, which includes neutrophils, eosinophils, mast cells, macrophages, basophils, and monocytes. Leukotriene biosynthesis begins with the specific oxidation of arachidonic acid by a free radical mechanism as a consequence of interaction with 5-LO. The first enzymatic step involves the abstraction of a hydrogen atom from C-7 of arachidonate followed by the addition of molecular oxygen to form 5-HpETE (5-hydroperoxyeicosatetraenoic acid). A second enzymatic step is also catalyzed by 5-LO and involves removal of a hydrogen atom from C-10, resulting in the formation of the conjugated triene epoxide LTA4. LTA4 must then be released by 5-LO and encounter either LTA4-H (LTA4 hydrolase) or LTC4-S [LTC4 (leukotriene C4) synthase]. LTA4-H can stereospecifically add water to C-12 while retaining a specific double-bond geometry, leading to LTB4 [leukotriene B4, 5(S),12(R)-dihydroxy-6,8,10,14-(Z,E,E,Z)-eicosatetraenoic acid]. If LTA4 encounters LTC4-S, then the reactive epoxide is opened at C-6 by the thiol anion of glutathione to form the product LTC4 [5(S)-hydroxy-6(R)-S-glutathyionyl-7,9,11,14- (E,E,Z,Z)-eicosatetraenoic acid], essentially a glutathionyl adduct of oxidized arachidonic acid. Both of these terminal leukotrienes are biologically active in that specific GPCRs recognize these chemical structures and receptor recognition initiates complex intracellular signalling cascades. In order for these molecules to serve as lipid mediators, however, they must be released from the biosynthetic cell into the extracellular milieu so that they can encounter the corresponding GPCRs. Surprising features of this cascade include the recognition of the assembly of critical enzymes at the perinuclear region of the cell and even localization of 5-LO within the nucleus of some cells. Under some situations, the budding phagosome has been found to assemble these proteins. Non-enzymatic proteins such as FLAP are now known as critical partners of this protein-machine assembly. An unexpected pathway of leukotriene biosynthesis involves the transfer of the chemically reactive intermediate, LTA4, from the biosynthetic cell followed by conversion into LTB4 or LTC4 by other cells that do not express 5-LO (PMID: 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?1582752175
Synonyms
ValueSource
(5S,12R,6Z,8E,10E,14Z)-5,12-Dihydroxy-6,8,10,14-eicosatetraenoic acidChEBI
(5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoic acidChEBI
(S-(R*,s*-(e,Z,e,Z)))-5,12-dihydroxy-6,8,10,14-eicosatetraenoic acidChEBI
5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-eicosatetraenoic acidChEBI
5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-icosatetraenoic acidChEBI
5,12-DiheteChEBI
5,12-HeteChEBI
5S,12R-Dihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acidChEBI
LTB4ChEBI
(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoateKegg
(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyicosa-6,8,10,14-tetraenoateKegg
(5S,12R,6Z,8E,10E,14Z)-5,12-Dihydroxy-6,8,10,14-eicosatetraenoateGenerator
(5S,6Z,8E,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoateGenerator
(S-(R*,s*-(e,Z,e,Z)))-5,12-dihydroxy-6,8,10,14-eicosatetraenoateGenerator
5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-eicosatetraenoateGenerator
5(S),12(R)-Dihydroxy-6(Z),8(e),10(e),14(Z)-icosatetraenoateGenerator
5S,12R-Dihydroxy-6Z,8E,10E,14Z-eicosatetraenoateGenerator
(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoic acidGenerator
(6Z,8E,10E,14Z)-(5S,12R)-5,12-Dihydroxyicosa-6,8,10,14-tetraenoic acidGenerator
5,12 HETEHMDB
5,12 DiHETEHMDB
Leukotriene b-4HMDB
Leukotrienes bHMDB
b-4, LeukotrieneHMDB
Leukotriene b 4HMDB
Leukotriene bHMDB
5,12-Dihydroxy-6,10-trans -8,14-cis -eicosatetraenoateHMDB
5,12-Dihydroxy-6,10-trans -8,14-cis -eicosatetraenoic acidHMDB
Leukotriene b4 ethanol solutionHMDB
(+)-Leukotriene b4HMDB
(5S,12R)-Leukotriene b4HMDB
5(S),12(R)-Dihydroxy-6-cis,8,10-trans,14-cis-eicosatetraenoic acidHMDB
Leucotriene b4HMDB
cis-Leukotriene b4HMDB
Leukotriene B4HMDB
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid
Traditional Nameleukotriene B4
CAS Registry Number71160-24-2
SMILES
CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t18-,19-/m1/s1
InChI KeyVNYSSYRCGWBHLG-AMOLWHMGSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentLeukotrienes
Alternative Parents
Substituents
  • Leukotriene
  • Hydroxyeicosatetraenoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker187.43530932474
[M-H]-Not Available187.435http://allccs.zhulab.cn/database/detail?ID=AllCCS00001866
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.015 g/LALOGPS
logP5.46ALOGPS
logP4.13ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity102.98 m³·mol⁻¹ChemAxon
Polarizability39.51 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]+193.02431661259
DarkChem[M-H]-187.38631661259
AllCCS[M+H]+190.77432859911
AllCCS[M-H]-187.88132859911
DeepCCS[M+H]+197.1830932474
DeepCCS[M-H]-194.58930932474
DeepCCS[M-2H]-229.11430932474
DeepCCS[M+Na]+204.45630932474
AllCCS[M+H]+190.832859911
AllCCS[M+H-H2O]+188.032859911
AllCCS[M+NH4]+193.432859911
AllCCS[M+Na]+194.132859911
AllCCS[M-H]-187.932859911
AllCCS[M+Na-2H]-189.732859911
AllCCS[M+HCOO]-191.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Leukotriene B4CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O4605.7Standard polar33892256
Leukotriene B4CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O2645.4Standard non polar33892256
Leukotriene B4CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O2873.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Leukotriene B4,1TMS,isomer #1CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C3003.9Semi standard non polar33892256
Leukotriene B4,1TMS,isomer #2CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C2997.2Semi standard non polar33892256
Leukotriene B4,1TMS,isomer #3CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C2902.7Semi standard non polar33892256
Leukotriene B4,2TMS,isomer #1CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C3062.5Semi standard non polar33892256
Leukotriene B4,2TMS,isomer #2CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2960.7Semi standard non polar33892256
Leukotriene B4,2TMS,isomer #3CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2958.3Semi standard non polar33892256
Leukotriene B4,3TMS,isomer #1CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3003.4Semi standard non polar33892256
Leukotriene B4,1TBDMS,isomer #1CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C3251.3Semi standard non polar33892256
Leukotriene B4,1TBDMS,isomer #2CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C3244.7Semi standard non polar33892256
Leukotriene B4,1TBDMS,isomer #3CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C3148.3Semi standard non polar33892256
Leukotriene B4,2TBDMS,isomer #1CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3518.0Semi standard non polar33892256
Leukotriene B4,2TBDMS,isomer #2CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3449.6Semi standard non polar33892256
Leukotriene B4,2TBDMS,isomer #3CCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3444.0Semi standard non polar33892256
Leukotriene B4,3TBDMS,isomer #1CCCCC/C=C\C[C@H](/C=C/C=C/C=C\[C@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3735.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Leukotriene B4 GC-MS (Non-derivatized) - 70eV, Positivesplash10-066r-7896000000-60973fb1d8ff05c73e4e2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Leukotriene B4 GC-MS (3 TMS) - 70eV, Positivesplash10-01rl-9113530000-205b0d713aeb42a9afc22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Leukotriene B4 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Leukotriene B4 LC-ESI-QIT , negative-QTOFsplash10-000i-0419000000-061132d646cd5dd85a1b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Leukotriene B4 LC-ESI-QIT , negative-QTOFsplash10-00ks-0829000000-7da7ab59ee0d4812767b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Leukotriene B4 LC-ESI-QIT , negative-QTOFsplash10-0002-0933000000-3fb381ce0f3609a902222017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Leukotriene B4 LC-ESI-QIT , negative-QTOFsplash10-0udj-0931000000-ccfdaa3226146fe9edc32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Leukotriene B4 LC-ESI-QIT , negative-QTOFsplash10-0udj-1940000000-ef988be204f5c54f4b212017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Leukotriene B4 LC-ESI-QIT , negative-QTOFsplash10-0r00-1910000000-e16cc958487f06dc42872017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Leukotriene B4 LC-ESI-QIT , negative-QTOFsplash10-0006-6900000000-a356f0334bf220eb54cc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Leukotriene B4 LC-ESI-QIT , negative-QTOFsplash10-052f-9700000000-66a6a217eba63b4874d12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Leukotriene B4 LC-ESI-QIT , negative-QTOFsplash10-0a4l-7900000000-aeb350579ea4a84117d02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Leukotriene B4 LC-ESI-QQ , negative-QTOFsplash10-000i-0619000000-dc49d3f4ab097db18f182017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 10V, Positive-QTOFsplash10-0gb9-0019000000-39d0f0947681f1f7fc372015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 20V, Positive-QTOFsplash10-0v4i-5498000000-4599d3006831091f926c2015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 40V, Positive-QTOFsplash10-052f-9450000000-b6647dcbb40f3175983d2015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 10V, Negative-QTOFsplash10-00kr-0029000000-d2d2e17f68f90518361e2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 20V, Negative-QTOFsplash10-014r-2269000000-1a60fcc2f712b3beea2a2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 40V, Negative-QTOFsplash10-0a4l-9340000000-edfb4e3fd8a8f4667ead2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 10V, Negative-QTOFsplash10-000i-0009000000-74962f74765b30de04ac2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 20V, Negative-QTOFsplash10-00kr-3659000000-98607094f1fa036e16e22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 40V, Negative-QTOFsplash10-052f-5191000000-91a6c7d4dfff9bd709672021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 10V, Positive-QTOFsplash10-0uxr-0019000000-bbfb0bde6a04ea9b05bc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 20V, Positive-QTOFsplash10-0udi-3439000000-d8140c418a63ad2159a32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leukotriene B4 40V, Positive-QTOFsplash10-0ar0-9320000000-afb563cb7a2b51e028362021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Locations
  • Epidermis
  • Leukocyte
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000037 +/- 0.000007 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0309 +/- 0.00178 uMInfant (0-1 year old)Not SpecifiedNormal details
BloodDetected and Quantified0.000296 +/- 0.000292 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00009686 +/- 0.0000062 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified<0.0001 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00011 +/- 0.00006 uMChildren (1-13 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000115 +/- 0.00005710 uMNot SpecifiedNot SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00363 +/- 0.000480 uMChildren (1-13 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000115 +/- 0.00005706 uMInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected and Quantified0 - 0.000005 umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified0.00003 +/- 0.000014 umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified<0.000000005 umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.082 uMInfant (0-1 year old)FemaleLeukotriene C4-Synthesis Deficiency details
BloodDetected and Quantified0.00015 +/- 0.00005 uMInfant (0-1 year old)Both
Postoperative pulmonary hypertension
details
BloodDetected and Quantified0.00016 +/- 0.00006 uMInfant (0-1 year old)Both
Postoperative pulmonary hypertension
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00477 +/- 0.000813 uMChildren (1-13 years old)Not SpecifiedAseptic meningitis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000177 uMAdult (>18 years old)Maleglutathione synthetase deficiency, acute metabolic crisis details
Cerebrospinal Fluid (CSF)Detected and Quantified<0.000149 uMNot SpecifiedNot Specifiedclosed head injury details
Cerebrospinal Fluid (CSF)Detected and Quantified<0.000149 uMNot SpecifiedNot Specifiedgunshot wound details
Cerebrospinal Fluid (CSF)Detected and Quantified<0.000595 uMNot SpecifiedNot Specifiedhydrocephalus details
Cerebrospinal Fluid (CSF)Detected and Quantified<0.000297 uMNot SpecifiedNot Specifiedmeningitis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00014 +/- 0.00002 uMChildren (1-13 years old)BothSjögren-Larsson syndrome details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0002 uMInfant (0-1 year old)FemaleLeukotriene C4-Synthesis Deficiency details
UrineDetected and Quantified<0.000000005 umol/mmol creatinineInfant (0-1 year old)FemaleLeukotriene C4-Synthesis Deficiency details
Associated Disorders and Diseases
Disease References
Cardiopulmonary bypass
  1. Pearl JM, Manning PB, McNamara JL, Saucier MM, Thomas DW: Effect of modified ultrafiltration on plasma thromboxane B2, leukotriene B4, and endothelin-1 in infants undergoing cardiopulmonary bypass. Ann Thorac Surg. 1999 Oct;68(4):1369-75. [PubMed:10543508 ]
Leukotriene C4-Synthesis Deficiency
  1. Mayatepek E, Flock B: Leukotriene C4-synthesis deficiency: a new inborn error of metabolism linked to a fatal developmental syndrome. Lancet. 1998 Nov 7;352(9139):1514-7. [PubMed:9820300 ]
Sjögren-Larsson syndrome
  1. Willemsen MA, Rotteveel JJ, de Jong JG, Wanders RJ, IJlst L, Hoffmann GF, Mayatepek E: Defective metabolism of leukotriene B4 in the Sjogren-Larsson syndrome. J Neurol Sci. 2001 Jan 15;183(1):61-7. [PubMed:11166796 ]
Aseptic meningitis
  1. Matsuo M, Hamasaki Y, Masuyama T, Ohta M, Miyazaki S: Leukotriene B4 and C4 in cerebrospinal fluid from children with meningitis and febrile seizures. Pediatr Neurol. 1996 Feb;14(2):121-4. [PubMed:8703223 ]
Glutathione synthetase deficiency
  1. Mayatepek E, Meissner T, Grobe H: Acute metabolic crisis with extreme deficiency of glutathione in combination with decreased levels of leukotriene C4 in a patient with glutathione synthetase deficiency. J Inherit Metab Dis. 2004;27(2):297-9. [PubMed:15243994 ]
Hydrocephalus
  1. Westcott JY, Murphy RC, Stenmark K: Eicosanoids in human ventricular cerebrospinal fluid following severe brain injury. Prostaglandins. 1987 Dec;34(6):877-87. [PubMed:2835791 ]
Meningitis
  1. Westcott JY, Murphy RC, Stenmark K: Eicosanoids in human ventricular cerebrospinal fluid following severe brain injury. Prostaglandins. 1987 Dec;34(6):877-87. [PubMed:2835791 ]
Associated OMIM IDs
  • 614037 (Leukotriene C4-Synthesis Deficiency)
  • 270200 (Sjögren-Larsson syndrome)
  • 266130 (Glutathione synthetase deficiency)
DrugBank IDDB12961
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC02165
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLeukotriene_B4
METLIN IDNot Available
PubChem Compound5280492
PDB IDNot Available
ChEBI ID15647
Food Biomarker OntologyNot Available
VMH IDLEUKTRB4
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceHan, Chao Qi; DiTullio, Dennis; Wang, Yi Fong; Sih, Charles J. A chemoenzymatic synthesis of leukotriene B4. Journal of Organic Chemistry (1986), 51(8), 1253-8.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Crocker I, Lawson N, Daniels I, Baker P, Fletcher J: Significance of fatty acids in pregnancy-induced immunosuppression. Clin Diagn Lab Immunol. 1999 Jul;6(4):587-93. [PubMed:10391868 ]
  2. Emingil G, Coker I, Atilla G, Huseyinov A: Levels of leukotriene B4 and platelet activating factor in gingival crevicular fluid in renal transplant patients receiving cyclosporine A. J Periodontol. 2000 Jan;71(1):50-7. [PubMed:10695938 ]
  3. Ahmadzadeh N, Shingu M, Nobunaga M, Tawara T: Relationship between leukotriene B4 and immunological parameters in rheumatoid synovial fluids. Inflammation. 1991 Dec;15(6):497-503. [PubMed:1661709 ]
  4. Lambiase A, Bonini S, Rasi G, Coassin M, Bruscolini A, Bonini S: Montelukast, a leukotriene receptor antagonist, in vernal keratoconjunctivitis associated with asthma. Arch Ophthalmol. 2003 May;121(5):615-20. [PubMed:12742837 ]
  5. Nathan H, Naveh N, Meyer E: Levels of prostaglandin E2 and leukotriene B4 in tears of vernal conjunctivitis patients during a therapeutic trial with indomethacin. Doc Ophthalmol. 1994;85(3):247-57. [PubMed:7924852 ]
  6. Yanagisawa Y, Nagai T: [The relationship between serum leukotriene B4 and smoking]. Nihon Eiseigaku Zasshi. 1993 Aug;48(3):698-706. [PubMed:8397308 ]
  7. Iversen L, Fogh K, Ziboh VA, Kristensen P, Schmedes A, Kragballe K: Leukotriene B4 formation during human neutrophil keratinocyte interactions: evidence for transformation of leukotriene A4 by putative keratinocyte leukotriene A4 hydrolase. J Invest Dermatol. 1993 Mar;100(3):293-8. [PubMed:8382716 ]
  8. Mancuso P, Nana-Sinkam P, Peters-Golden M: Leukotriene B4 augments neutrophil phagocytosis of Klebsiella pneumoniae. Infect Immun. 2001 Apr;69(4):2011-6. [PubMed:11254552 ]
  9. Mozalevskii AF, Travianko TD, Iakovlev AA, Smirnova EA, Novikova NP, Sapa IIu: [Content of arachidonic acid metabolites in blood and saliva of children with bronchial asthma]. Ukr Biokhim Zh (1978). 1997 Sep-Dec;69(5-6):162-8. [PubMed:9606840 ]
  10. Shindo K, Koide K, Fukumura M: Enhancement of leukotriene B4 release in stimulated asthmatic neutrophils by platelet activating factor. Thorax. 1997 Dec;52(12):1024-9. [PubMed:9516893 ]
  11. Sieunarine K, Lawrence-Brown MM, Goodman MA, Prendergast FJ, Rocchetta S: Plasma levels of the lipid mediators, leukotriene B4 and lyso platelet-activating factor, in intraoperative salvaged blood. Vox Sang. 1992;63(3):168-71. [PubMed:1333134 ]
  12. Blackburn WD Jr, Heck LW, Loose LD, Eskra JD, Carty TJ: Inhibition of 5-lipoxygenase product formation and polymorphonuclear cell degranulation by tenidap sodium in patients with rheumatoid arthritis. Arthritis Rheum. 1991 Feb;34(2):204-10. [PubMed:1847289 ]
  13. Soyombo O, Spur BW, Soh C, Lee TH: Structure/activity relationship of leukotriene B4 and its structural analogues in chemotactic, lysosomal-enzyme release and receptor-binding assays. Eur J Biochem. 1993 Nov 15;218(1):59-66. [PubMed:8243477 ]
  14. Garcia-Pastor P, Randazzo A, Gomez-Paloma L, Alcaraz MJ, Paya M: Effects of petrosaspongiolide M, a novel phospholipase A2 inhibitor, on acute and chronic inflammation. J Pharmacol Exp Ther. 1999 Apr;289(1):166-72. [PubMed:10087000 ]
  15. Nieminen MM, Moilanen EK, Koskinen MO, Karvonen JI, Tuomisto L, Metsa-Ketela TJ, Vapaatalo H: Inhaled budesonide fails to inhibit the PAF-induced increase in plasma leukotriene B4 in man. Br J Clin Pharmacol. 1992 Jun;33(6):645-52. [PubMed:1327049 ]
  16. Seyger MM, van Pelt JP, van den Born J, Latijnhouwers MA, de Jong EM: Epicutaneous application of leukotriene B4 induces patterns of tenascin and a heparan sulfate proteoglycan epitope that are typical for psoriatic lesions. Arch Dermatol Res. 1997 May;289(6):331-6. [PubMed:9209678 ]
  17. Berry KA, Borgeat P, Gosselin J, Flamand L, Murphy RC: Urinary metabolites of leukotriene B4 in the human subject. J Biol Chem. 2003 Jul 4;278(27):24449-60. Epub 2003 Apr 22. [PubMed:12709426 ]
  18. Pacheco Y, Hosni R, Chabannes B, Gormand F, Moliere P, Grosclaude M, Piperno D, Lagarde M, Perrin-Fayolle M: Leukotriene B4 level in stimulated blood neutrophils and alveolar macrophages from healthy and asthmatic subjects. Effect of beta-2 agonist therapy. Eur J Clin Invest. 1992 Nov;22(11):732-9. [PubMed:1335872 ]
  19. Bentancur AG, Naveh N, Lancri J, Selah BA, Livneh A: Urine leukotriene B4 in familial Mediterranean fever. Clin Exp Rheumatol. 2004 Jul-Aug;22(4 Suppl 34):S56-8. [PubMed:15515787 ]
  20. Fogh J, Poulsen LK, Bisgaard H: A specific assay for leukotriene B4 in human whole blood. J Pharmacol Toxicol Methods. 1992 Dec;28(4):185-90. [PubMed:1338371 ]
  21. Murphy RC, Gijon MA: Biosynthesis and metabolism of leukotrienes. Biochem J. 2007 Aug 1;405(3):379-95. [PubMed:17623009 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP4F2
Uniprot ID:
P78329
Molecular weight:
59852.825
Reactions
Leukotriene B4 + NADPH + Oxygen → 20-Hydroxy-leukotriene B4 + NADP + Waterdetails
Leukotriene B4 + NADPH + Hydrogen Ion + Oxygen → 20-Hydroxy-leukotriene B4 + NADP + Waterdetails
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. This enzyme requires molecular oxygen and NADPH for the omega-hydroxylation of LTB4, a potent chemoattractant for polymorphonuclear leukocytes.
Gene Name:
CYP4F3
Uniprot ID:
Q08477
Molecular weight:
59846.085
Reactions
Leukotriene B4 + NADPH + Oxygen → 20-Hydroxy-leukotriene B4 + NADP + Waterdetails
Leukotriene B4 + NADPH + Hydrogen Ion + Oxygen → 20-Hydroxy-leukotriene B4 + NADP + Waterdetails
General function:
Involved in binding
Specific function:
Epoxide hydrolase that catalyzes the final step in the biosynthesis of the proinflammatory mediator leukotriene B4. Has also aminopeptidase activity.
Gene Name:
LTA4H
Uniprot ID:
P09960
Molecular weight:
69284.64
Reactions
Leukotriene A4 + Water → Leukotriene B4details
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Not Available
Gene Name:
CYP4F11
Uniprot ID:
Q9HBI6
Molecular weight:
60145.165
Reactions
Leukotriene B4 + NADPH + Hydrogen Ion + Oxygen → 20-Hydroxy-leukotriene B4 + NADP + Waterdetails
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Hydroxylates arachidonic acid (20:4n-6) to (18R)-hydroxyarachidonate. Shows little activity against prostaglandin (PG) D2, PGE1, PGE2, PGF2alpha, and leukotriene B4. Catalyzes omega-2 and omega-3-hydroxylation of PGH1 and PGH2. Catalyzes epoxidation of 4,7,10,13,16,19-(Z)-docosahexaenoic acid (22:6n-3) and 7,10,13,16,19-(Z)-docosapentaenoic acid (22:5n-3) and omega-3-hydroxylation of 4,7,10,13,16-(Z)-docosapentaenoic acid (22:5n-6). Catalyzes hydroxylation of PGI2 and carbaprostacyclin.
Gene Name:
CYP4F8
Uniprot ID:
P98187
Molecular weight:
59993.995
Reactions
Leukotriene B4 + NADPH + Hydrogen Ion + Oxygen → 20-Hydroxy-leukotriene B4 + NADP + Waterdetails
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for extracellular ATP > UTP and ADP. The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol-calcium second messenger system. May be the cardiac P2Y receptor involved in the regulation of cardiac muscle contraction through modulation of L-type calcium currents. Is a receptor for leukotriene B4, a potent chemoattractant involved in inflammation and immune response
Gene Name:
LTB4R
Uniprot ID:
Q15722
Molecular weight:
37556.9
General function:
Involved in transcription regulator activity
Specific function:
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues
Gene Name:
AHR
Uniprot ID:
P35869
Molecular weight:
96146.7
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Low-affinity receptor for leukotrienes including leukotriene B4. Mediates chemotaxis of granulocytes and macrophages. The response is mediated via G-proteins that activate a phosphatidylinositol-calcium second messenger system. The rank order of affinities for the leukotrienes is LTB4 > 12-epi-LTB4 > LTB5 > LTB3
Gene Name:
LTB4R2
Uniprot ID:
Q9NPC1
Molecular weight:
41524.3
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP4F22
Uniprot ID:
Q6NT55
Molecular weight:
Not Available
Reactions
Leukotriene B4 + NADPH + Hydrogen Ion + Oxygen → 20-Hydroxy-leukotriene B4 + NADP + Waterdetails