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CHEBI:15647 - leukotriene B4

ChEBI IDCHEBI:15647
ChEBI Nameleukotriene B4
Stars
ASCII Nameleukotriene B4
DefinitionA 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.
Secondary ChEBI IDsCHEBI:6421, CHEBI:10933, CHEBI:25024
Last Modified10 June 2021
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC20H32O4
Net Charge0
Average Mass336.472
Monoisotopic Mass336.23006
SMILESCCCCC/C=C\C[C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(=O)O
InChIInChI=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
InChIKeyVNYSSYRCGWBHLG-AMOLWHMGSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Mus musculus (ncbitaxon:10090) - PubMed (19425150) Source: BioModels - MODEL1507180067
Phaseolus vulgaris (ncbitaxon:3885) - DOI (10.3390/ijms19041049)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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).
Application:
vasoconstrictor agent  Drug used to cause constriction of the blood vessels.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
10,11-dihydro-12-oxoleukotriene B4 (CHEBI:134417) has functional parent leukotriene B4 (CHEBI:15647)
10,11-dihydro-20,20-dihydroxyleukotriene B4 (CHEBI:134437) has functional parent leukotriene B4 (CHEBI:15647)
10,11-dihydro-20,20,20-trihydroxyleukotriene B4 (CHEBI:134442) 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)
12,20-dioxoleukotriene B4 (CHEBI:134520) 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-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)
20,20-dihydroxyleukotriene B4 (CHEBI:134516) has functional parent leukotriene B4 (CHEBI:15647)
20,20,20-trihydroxyleukotriene B4 (CHEBI:134515) 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  Source
Leukotriene B4KEGG COMPOUND
5,12-DiheteChEBI
5,12-HeteChemIDplus
(S-(R*,S*-(E,Z,E,Z)))-5,12-Dihydroxy-6,8,10,14-eicosatetraenoic acidChemIDplus
LTB4ChemIDplus
5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acidLIPID MAPS
Manual XrefsDatabases
C02165KEGG COMPOUND
LMFA03020001LIPID MAPS
Leukotriene_B4Wikipedia
HMDB0001085HMDB
4444132ChemSpider
LTBPDBeChem
DB12961DrugBank
C00053425KNApSAcK
Registry NumbersSources
Reaxys:4235309Reaxys
CAS:71160-24-2KEGG COMPOUND
CAS:71160-24-2ChemIDplus
Citations