CHEBI:28666 - leukotriene D4

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ChEBI Name leukotriene D4
ChEBI ID CHEBI:28666
ChEBI ASCII Name leukotriene D4
Definition A leukotriene that is (7E,9E,11Z,14Z)-icosa-7,9,11,14-tetraenoic acid substituted by a hydroxy group at position 5 (5S) and a L-cysteinylglycinyl group at position 6 (6R).
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:6423, CHEBI:25026
Supplier Information ZINC000004632133
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Leukotriene D4 (LTD4) is one of the leukotrienes. Its main function in the body is to induce the contraction of smooth muscle, resulting in bronchoconstriction and vasoconstriction. It also increases vascular permeability. LTD4 is released by basophils. Other leukotrienes that function in a similar manner are leukotrienes C4 and E4. Pharmacological agents that inhibit the function of these leukotrienes are leukotriene receptor antagonists (e.g., zafirlukast, montelukast) and are useful for asthmatic individuals.
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Formulae C25H40N2O6S
C25H40N2O6S
Net Charge 0
Average Mass 496.66000
Monoisotopic Mass 496.26071
InChI InChI=1S/C25H40N2O6S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-22(21(28)15-14-17-23(29)30)34-19-20(26)25(33)27-18-24(31)32/h6-7,9-13,16,20-22,28H,2-5,8,14-15,17-19,26H2,1H3,(H,27,33)(H,29,30)(H,31,32)/b7-6-,10-9-,12-11+,16-13+/t20-,21-,22+/m0/s1
InChIKey YEESKJGWJFYOOK-IJHYULJSSA-N
SMILES CCCCC\C=C/C\C=C/C=C/C=C/[C@@H](SC[C@H](N)C(=O)NCC(O)=O)[C@@H](O)CCCC(O)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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).
Application(s): bronchoconstrictor agent
A drug which causes a narrowing of the lumen of a bronchus or bronchiole.
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ChEBI Ontology
Outgoing leukotriene D4 (CHEBI:28666) has functional parent icosa-7,9,11,14-tetraenoic acid (CHEBI:36038)
leukotriene D4 (CHEBI:28666) has role bronchoconstrictor agent (CHEBI:50141)
leukotriene D4 (CHEBI:28666) has role human metabolite (CHEBI:77746)
leukotriene D4 (CHEBI:28666) has role mouse metabolite (CHEBI:75771)
leukotriene D4 (CHEBI:28666) is a dipeptide (CHEBI:46761)
leukotriene D4 (CHEBI:28666) is a leukotriene (CHEBI:25029)
leukotriene D4 (CHEBI:28666) is a organic sulfide (CHEBI:16385)
leukotriene D4 (CHEBI:28666) is conjugate acid of leukotriene D4(1−) (CHEBI:63166)
Incoming leukotriene D4(1−) (CHEBI:63166) is conjugate base of leukotriene D4 (CHEBI:28666)
IUPAC Name
S-{(1R,2E,4E,6Z,9Z)-1-[(1S)-4-carboxy-1-hydroxybutyl]pentadeca-2,4,6,9-tetraen-1-yl}-L-cysteinylglycine
Synonyms Sources
(R-(R*,S*-(E,E,Z,Z)))-N-(S-(1-(4-Carboxy-1-hydroxybutyl)-2,4,6,9-pentadecatetraenyl)-L-cysteinyl)glycine ChemIDplus
5S-hydroxy-6R-(S-cysteinylglycinyl)-7E,9E,11E,14Z-eicosatetraenoic acid LIPID MAPS
Leukotriene D4 KEGG COMPOUND
LTD4 KEGG COMPOUND
Manual Xrefs Databases
C05951 KEGG COMPOUND
HMDB0003080 HMDB
Leukotriene_D4 Wikipedia
LMFA03020006 LIPID MAPS
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Registry Numbers Types Sources
4726738 Reaxys Registry Number Reaxys
73836-78-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
23825762 PubMed citation Europe PMC
9160411 PubMed citation Europe PMC
Last Modified
21 February 2017