Compound
leukotriene A4
(2S-(2 alpha,3 beta(1E,3E,5Z,8Z)))-3-(1,3,5,8-Tetradecatetraenyl)oxiranebutanoic acid. An unstable allylic epoxide, formed from the immediate precursor 5-hpete via the stereospecific removal of a proton at C-10 and dehydration. Its biological actions are determined primarily by its metabolites, i.e., leukotriene B4 and cysteinyl-leukotrienes. Alternatively, leukotriene A4 is converted into leukotriene C4 by glutathione-S-transferase or into 5,6-di-hete by the epoxide-hydrolase. (From Dictionary of Prostaglandins and Related Compounds, 1990)
Structure
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- Class
- Organic compound, anion
- Formula
- C20H29O3
- Mass
- 317.449 g/mol
- Charge
- -1
- InChIKey
- UFPQIRYSPUYQHK-WAQVJNLQSA-M
- SMILES
- CCCCC/C=CC/C=CC=CC=C[C@@H]1O[C@H]1CCCC(=O)[O-]
- Look it up
- ChEBIPubChemBy InChIKey
Identity from ChEBI, geometry from PubChem. Not evidence.
What it touches on the way
Mechanistic reach
10 entities
10 entities reached.
0 reported hops10 assembled from the scaffold
- ALOX12ProteinUNIPROT:P18054substrate ofInferred only112 paths28 endpoints
- ALOX5ProteinUNIPROT:P09917substrate ofInferred only110 paths55 endpoints
- LTC4SProteinUNIPROT:Q16873substrate ofInferred only60 paths20 endpoints
- LTA4HProteinUNIPROT:P09960substrate ofInferred only60 paths30 endpoints
- GSTM4ProteinUNIPROT:Q03013metabolized byInferred only26 paths26 endpoints
- SLCO2A1ProteinUNIPROT:Q92959transported byInferred only14 paths13 endpoints
- MGST3ProteinUNIPROT:O14880substrate ofInferred only11 paths11 endpoints
- MGST2ProteinUNIPROT:Q99735substrate ofInferred only10 paths10 endpoints
- SLCO1B1ProteinUNIPROT:Q9Y6L6transported byInferred only9 paths2 endpoints
- RNPEPProteinUNIPROT:Q9H4A4substrate ofInferred only4 paths4 endpoints
What the reference databases state
Statements
23 statements
23 statements · 2 reference databases · Subject: leukotriene A4 · Sources: Human-GEM, Rhea
- (5S)-hydroperoxy-(6E,8Z,11Z,14Z)-eicosatetraenoate is converted to leukotriene A4CompoundRhea RHEA:17961Inferred only
- (5Z,8Z,11Z,14Z)-eicosatetraenoate is converted to leukotriene A4CompoundRhea RHEA:32307Inferred only
- 5(S)-HPETE is converted to leukotriene A4CompoundHuman-GEM MAR00959Inferred only
- leukotriene A4 is metabolised by GSTM4ProteinRhea RHEA:17617Inferred only
- leukotriene A4 is a substrate of ALOX12ProteinHuman-GEM MAR01096Inferred only
- leukotriene A4 is a substrate of ALOX12ProteinHuman-GEM MAR01093Inferred only
- leukotriene A4 is a substrate of ALOX12ProteinRhea RHEA:48584Inferred only
- leukotriene A4 is a substrate of ALOX12ProteinRhea RHEA:48588Inferred only
- leukotriene A4 is a substrate of ALOX5ProteinHuman-GEM MAR01096Inferred only
- leukotriene A4 is a substrate of ALOX5ProteinHuman-GEM MAR01093Inferred only
- leukotriene A4 is a substrate of LTA4HProteinHuman-GEM MAR01080Inferred only
- leukotriene A4 is a substrate of LTA4HProteinRhea RHEA:22324Inferred only
Show the remaining 11
- leukotriene A4 is a substrate of LTC4SProteinHuman-GEM MAR08550Inferred only
- leukotriene A4 is a substrate of LTC4SProteinRhea RHEA:17617Inferred only
- leukotriene A4 is a substrate of LTC4SProteinHuman-GEM MAR01081Inferred only
- leukotriene A4 is a substrate of MGST2ProteinRhea RHEA:17617Inferred only
- leukotriene A4 is a substrate of MGST3ProteinRhea RHEA:17617Inferred only
- leukotriene A4 is a substrate of RNPEPProteinHuman-GEM MAR01080Inferred only
- leukotriene A4 is transported by SLC22A10ProteinHuman-GEM MAR06254Inferred only
- leukotriene A4 is transported by SLCO1B1ProteinHuman-GEM MAR06148Inferred only
- leukotriene A4 is transported by SLCO1B1ProteinHuman-GEM MAR06150Inferred only
- leukotriene A4 is transported by SLCO1B1ProteinHuman-GEM MAR06149Inferred only
- leukotriene A4 is transported by SLCO2A1ProteinHuman-GEM MAR06221Inferred only
Reactions
22 reactions
5(S)-HPETEwater+leukotriene A4
Catalysed by ALOX5
Reaction pageLeft to rightBalancedEC 1.13.11.34cytosol
Human-GEM MAR00959CC BY 4.0Reference data
water+leukotriene A4MAM02364c
Reaction pageLeft to rightBalancedEC 3.3.2.6, 3.4.11.6cytosol
Human-GEM MAR01080CC BY 4.0Reference data
CHEBI:16856+leukotriene A4leukotriene C4
Catalysed by LTC4S
Reaction pageLeft to rightBalancedEC 4.4.1.20cytosol
Human-GEM MAR01081CC BY 4.0Reference data
water+leukotriene A4MAM00320c
Reaction pageLeft to rightBalancedcytosol
Human-GEM MAR01092CC BY 4.0Reference data
MAM01058c+water+NADP(3-)proton+leukotriene A4+NADPH(4-)+dioxygen
Reaction pageReversibleBalancedEC 1.13.11.31, 1.13.11.34cytosol
Human-GEM MAR01093CC BY 4.0Reference data
Reaction pageReversibleBalancedcytosol, nucleus
Human-GEM MAR01094CC BY 4.0Reference data
proton+leukotriene A4+NADPH(4-)+dioxygenMAM01058n+water+NADP(3-)
Reaction pageLeft to rightBalancedEC 1.13.11.31, 1.13.11.34nucleus
Human-GEM MAR01096CC BY 4.0Reference data
MAM01980c+hydrogencarbonate+leukotriene A4MAM01980e+hydrogencarbonate+leukotriene A4
Transported by SLCO1B1
Reaction pageReversibleBalance undeterminablecytosol, extracellular space
Human-GEM MAR06148CC BY 4.0Reference data
hydrogencarbonate+leukotriene A4+2,4-dinitrophenyl-S-glutathionehydrogencarbonate+leukotriene A4+2,4-dinitrophenyl-S-glutathione
Transported by SLCO1B1
Reaction pageReversibleBalancedcytosol, extracellular space
Human-GEM MAR06149CC BY 4.0Reference data
hydrogencarbonate+leukotriene A4+MAM02901chydrogencarbonate+leukotriene A4+MAM02901e
Transported by SLCO1B1
Reaction pageReversibleBalancedcytosol, extracellular space
Human-GEM MAR06150CC BY 4.0Reference data
CHEBI:16856+hydrogencarbonate+leukotriene A4CHEBI:16856+hydrogencarbonate+leukotriene A4
Transported by SLCO2A1
Reaction pageReversibleBalancedcytosol, extracellular space
Human-GEM MAR06221CC BY 4.0Reference data
Transported by SLC22A10
Reaction pageReversibleBalancedcytosol, extracellular space
Human-GEM MAR06254CC BY 4.0Reference data
Where it reaches
5 systems, 8 regions, 15 tissues, 15 transporter routes — routes, not measurements: transporters known to carry leukotriene A4 are expressed there, and no source reports it arriving.
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Other names
7 names
Resolves to: leukotriene A4
- Also called
- (7E,9E,11Z,14Z)-(5S,6S)-5,6-epoxyicosa-7,9,11,14-tetraenoateleukotriene A4 anionLTA4LTA4 anionLTA4(1-)LTA4(1−)
- Systematic name
- (5S,6S,7E,9E,11Z,14Z)-5,6-epoxyicosa-7,9,11,14-tetraenoate