CHEBI:15647 - leukotriene B4

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ChEBI Name leukotriene B4
ChEBI ID CHEBI:15647
ChEBI ASCII Name leukotriene B4
Definition A leukotriene composed of (6Z,8E,10E,14Z)-icosatetraenoic acid having (5S)- and (12R)-hydroxy substituents. It is a lipid mediator of inflammation that is generated from arachidonic acid via the 5-lipoxygenase pathway.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:6421, CHEBI:10933, CHEBI:25024
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Formula C20H32O4
Net Charge 0
Average Mass 336.472
Monoisotopic Mass 336.23006
InChI 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
InChIKey VNYSSYRCGWBHLG-AMOLWHMGSA-N
SMILES CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Phaseolus vulgaris (NCBI:txid3885) See: DOI
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): vasoconstrictor agent
Drug used to cause constriction of the blood vessels.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing leukotriene B4 (CHEBI:15647) has functional parent icosa-6,8,10,14-tetraenoic acid (CHEBI:36045)
leukotriene B4 (CHEBI:15647) has role human metabolite (CHEBI:77746)
leukotriene B4 (CHEBI:15647) has role mouse metabolite (CHEBI:75771)
leukotriene B4 (CHEBI:15647) has role plant metabolite (CHEBI:76924)
leukotriene B4 (CHEBI:15647) has role vasoconstrictor agent (CHEBI:50514)
leukotriene B4 (CHEBI:15647) is a dihydroxy monocarboxylic acid (CHEBI:35972)
leukotriene B4 (CHEBI:15647) is a hydroxy polyunsaturated fatty acid (CHEBI:140345)
leukotriene B4 (CHEBI:15647) is a leukotriene (CHEBI:25029)
leukotriene B4 (CHEBI:15647) is a long-chain fatty acid (CHEBI:15904)
leukotriene B4 (CHEBI:15647) is conjugate acid of leukotriene B4(1−) (CHEBI:57461)
Incoming 10,11-dihydro-12-oxoleukotriene B4 (CHEBI:134417) has functional parent leukotriene B4 (CHEBI:15647)
10,11-dihydro-20,20,20-trihydroxyleukotriene B4 (CHEBI:134442) has functional parent leukotriene B4 (CHEBI:15647)
10,11-dihydro-20,20-dihydroxyleukotriene B4 (CHEBI:134437) has functional parent leukotriene B4 (CHEBI:15647)
12,20-dioxoleukotriene B4 (CHEBI:134520) has functional parent leukotriene B4 (CHEBI:15647)
12-dehydro-leukotriene B4 (CHEBI:27814) has functional parent leukotriene B4 (CHEBI:15647)
12-oxo-20-hydroxyleukotriene B4 (CHEBI:134456) has functional parent leukotriene B4 (CHEBI:15647)
18-hydroxy-18-oxo-dinorleukotriene B4 (CHEBI:63980) has functional parent leukotriene B4 (CHEBI:15647)
18-hydroxyleukotriene B4 (CHEBI:138201) has functional parent leukotriene B4 (CHEBI:15647)
19-hydroxyleukotriene B4 (CHEBI:138196) has functional parent leukotriene B4 (CHEBI:15647)
20,20,20-trihydroxyleukotriene B4 (CHEBI:134515) has functional parent leukotriene B4 (CHEBI:15647)
20,20-dihydroxyleukotriene B4 (CHEBI:134516) has functional parent leukotriene B4 (CHEBI:15647)
20-hydroxy-20-oxoleukotriene B4 (CHEBI:27562) has functional parent leukotriene B4 (CHEBI:15647)
20-hydroxy-leukotriene B4 (CHEBI:15646) has functional parent leukotriene B4 (CHEBI:15647)
leukotriene B4(1−) (CHEBI:57461) is conjugate base of leukotriene B4 (CHEBI:15647)
IUPAC Name
(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid
Synonyms Sources
(5S,12R,6Z,8E,10E,14Z)-5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid ChEBI
(5S,6Z,8E,10E,12R,14Z)-5,12-dihydroxyeicosa-6,8,10,14-tetraenoic acid ChEBI
(S-(R*,S*-(E,Z,E,Z)))-5,12-Dihydroxy-6,8,10,14-eicosatetraenoic acid ChemIDplus
5(S),12(R)-dihydroxy-6(Z),8(E),10(E),14(Z)-eicosatetraenoic acid ChEBI
5(S),12(R)-dihydroxy-6(Z),8(E),10(E),14(Z)-icosatetraenoic acid ChEBI
5,12-Dihete ChEBI
5,12-Hete ChemIDplus
5S,12R-diHETE LIPID MAPS
5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acid LIPID MAPS
Leukotriene B4 KEGG COMPOUND
LTB4 ChEBI
LTB4 ChemIDplus
LTB4 KEGG COMPOUND
Manual Xrefs Databases
4444132 ChemSpider
C00053425 KNApSAcK
C02165 KEGG COMPOUND
DB12961 DrugBank
HMDB0001085 HMDB
Leukotriene_B4 Wikipedia
LMFA03020001 LIPID MAPS
LTB PDBeChem
View more database links
Registry Numbers Types Sources
4235309 Reaxys Registry Number Reaxys
71160-24-2 CAS Registry Number KEGG COMPOUND
71160-24-2 CAS Registry Number ChemIDplus
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Last Modified
10 June 2021
General Comment
2011-03-17 A leukotriene involved in inflammation. It is produced from leukocytes in response to inflammatory mediators and is able to induce the adhesion and activation of leukocytes on the endothelium, allowing them to bind to and cross it into the tissue.