You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 14:59:18 UTC
Secondary Accession Numbers
  • HMDB01337
Metabolite Identification
Common NameLeukotriene A4
DescriptionLeukotriene A4 (LTA4) is the first metabolite in the series of reactions leading to the synthesis of all leukotrienes. 5-Lipoxygenase (5-LO) catalyzes the two-step conversion of arachidonic acid to LTA4.The first step consists of the oxidation of arachidonic acid to the unstable intermediate 5-hydroperoxyeicosatetraenoic acid (5-HPETE), and the second step is the dehydration of 5-HPETE to form LTA4. Leukotriene A4, an unstable epoxide, is hydrolyzed to leukotriene B4 or conjugated with glutathione to yield leukotriene C4 and its metabolites, leukotriene D4 and leukotriene E4. The leukotrienes participate in host defense reactions and pathophysiological conditions such as immediate hypersensitivity and inflammation. Recent studies also suggest a neuroendocrine role for leukotriene C4 in luteinizing hormone secretion. (PMID: 10591081 , 2820055 ). 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.
(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyeicosa-7,9,11,14-tetraenoic acidChEBI
5(S)-5,6-Oxido-7,9-trans-11,14-cis-eicosatetraenoic acidChEBI
5S,6S-Epoxy-7E,9E,11Z,14Z-eicosatetraenoic acidChEBI
5S,6S-Leukotriene a4ChEBI
(5S,6S,7E,9E,11Z,14Z)-5,6-Epoxyicosa-7,9,11,14-tetraenoic acidGenerator
(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa-7,9,11,14-tetraenoic acidGenerator
(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa- 7,9,11,14-tetraenoateHMDB
(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa- 7,9,11,14-tetraenoic acidHMDB
(7E,9E,11Z,14Z)-(5S,6S)-5,6-Epoxyicosa-7,9,11,14-tetrenoioc acidHMDB
Leukotriene aHMDB
Leukotriene a 4HMDB
Leukotrienes aHMDB
Leukotriene a-4HMDB
Chemical FormulaC20H30O3
Average Molecular Weight318.4504
Monoisotopic Molecular Weight318.219494826
IUPAC Name4-[(2S,3S)-3-[(1E,3E,5Z,8Z)-tetradeca-1,3,5,8-tetraen-1-yl]oxiran-2-yl]butanoic acid
Traditional Nameleukotriene A4
CAS Registry Number72059-45-1
InChI Identifier
Chemical Taxonomy
Description Belongs to the class of organic compounds known as epoxy fatty acids. These are fatty acids containing an oxirane ring as part of the aliphatic chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentEpoxy fatty acids
Alternative Parents
  • Epoxy fatty acid
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors

Route of exposure:


Biological location:


Naturally occurring process:


Industrial application:

Biological role:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.00042 g/LALOGPS
pKa (Strongest Acidic)4.49ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.83 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity99.32 m³·mol⁻¹ChemAxon
Polarizability37.95 ųChemAxon
Number of Rings1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon


Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uec-8290000000-c9cb5a94725e337cb3e02017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00gr-9143000000-62d8773d6e2e97f538922017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0uec-8290000000-c9cb5a94725e337cb3e02021-09-05View Spectrum


Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-1129000000-fffe04743dab285e2ca82016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052g-9421000000-f30ef9628caae676c4c02016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9610000000-5d083c3562218df21b532016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0139000000-39394fbcd6b959bb3bf72016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-4396000000-97fa16078ceabe3f07db2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9230000000-62723f520381db54d71c2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-3529000000-0fbbeee57f59de11f1772021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fyn-9533000000-d9537938ec7f6d2477572021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9100000000-e99fd57f045ac7fdae482021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-144e64ffbb4253ee3d972021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-6339000000-eb15f4eeced3dd8bfaed2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9320000000-a3755453c278384f23ba2021-09-08View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biospecimen LocationsNot Available
Tissue Locations
  • Epidermis
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 IDFDB022561
KNApSAcK IDNot Available
Chemspider ID4444074
KEGG Compound IDC00909
BioCyc IDNot Available
BiGG ID36355
Wikipedia LinkLeukotriene
PubChem Compound5280383
PDB IDNot Available
ChEBI ID15651
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Luscinskas FW, Nicolaou KC, Webber SE, Veale CA, Gimbrone MA Jr, Serhan CN: Ca2+ mobilization with leukotriene A4 and epoxytetraenes in human neutrophils. Biochem Pharmacol. 1990 Jan 15;39(2):355-65. [PubMed:2154229 ]
  2. 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 ]
  3. MacMillan DK, Hill E, Sala A, Sigal E, Shuman T, Henson PM, Murphy RC: Eosinophil 15-lipoxygenase is a leukotriene A4 synthase. J Biol Chem. 1994 Oct 28;269(43):26663-8. [PubMed:7929400 ]
  4. Iversen L, Ziboh VA, Shimizu T, Ohishi N, Radmark O, Wetterholm A, Kragballe K: Identification and subcellular localization of leukotriene A4-hydrolase activity in human epidermis. J Dermatol Sci. 1994 Jun;7(3):191-201. [PubMed:7918238 ]
  5. Nicholson DW, Klemba MW, Rasper DM, Metters KM, Zamboni RJ, Ford-Hutchinson AW: Purification of human leukotriene C4 synthase from dimethylsulfoxide-differentiated U937 cells. Eur J Biochem. 1992 Oct 15;209(2):725-34. [PubMed:1425677 ]
  6. Silverman ES, Drazen JM: The biology of 5-lipoxygenase: function, structure, and regulatory mechanisms. Proc Assoc Am Physicians. 1999 Nov-Dec;111(6):525-36. [PubMed:10591081 ]
  7. Samuelsson B, Dahlen SE, Lindgren JA, Rouzer CA, Serhan CN: Leukotrienes and lipoxins: structures, biosynthesis, and biological effects. Science. 1987 Sep 4;237(4819):1171-6. [PubMed:2820055 ]


General function:
Involved in enzyme activator activity
Specific function:
Catalyzes the conjugation of leukotriene A4 with reduced glutathione to form leukotriene C4.
Gene Name:
Uniprot ID:
Molecular weight:
Leukotriene A4 + Glutathione → Leukotriene C4details
General function:
Involved in metal ion binding
Specific function:
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:
Uniprot ID:
Molecular weight:
5(S)-Hydroperoxyeicosatetraenoic acid → Leukotriene A4 + Waterdetails
Arachidonic acid + Oxygen → Leukotriene A4 + 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:
Uniprot ID:
Molecular weight:
Leukotriene A4 + Water → Leukotriene B4details