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CHEBI:52450 - 2-O-acetyl-1-O-octadecyl-sn-glycero-3-phosphocholine

ChEBI IDCHEBI:52450
ChEBI Name2-O-acetyl-1-O-octadecyl-sn-glycero-3-phosphocholine
Stars
ASCII Name2-O-acetyl-1-O-octadecyl-sn-glycero-3-phosphocholine
DefinitionA 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine betaine which has octadecyl as the alkyl group. PAF is a potent phospholipid activator and mediator of many leukocyte functions, including platelet aggregation, inflammation, and anaphylaxis.
Secondary ChEBI IDsCHEBI:26164, CHEBI:52390, CHEBI:75217
Last Modified2 December 2016
SubmitterBijay, laimo, Marcus Ennis
DownloadsMolfile
FormulaC28H58NO7P
Net Charge0
Average Mass551.746
Monoisotopic Mass551.39509
SMILESCCCCCCCCCCCCCCCCCCOC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(C)=O
InChIInChI=1S/C28H58NO7P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-23-33-25-28(36-27(2)30)26-35-37(31,32)34-24-22-29(3,4)5/h28H,6-26H2,1-5H3/t28-/m1/s1
InChIKeyZXCIEWBDUAPBJF-MUUNZHRXSA-N
Wikipedia
Roles Classification
Biological Role:
beta-adrenergic antagonist  An agent that binds to but does not activate β-adrenergic receptors thereby blocking the actions of endogenous or exogenous β-adrenergic agonists. β-Adrenergic antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches and anxiety.
Applications:
hematologic agent  Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.
vasodilator agent  A drug used to cause dilation of the blood vessels.
beta-adrenergic antagonist  An agent that binds to but does not activate β-adrenergic receptors thereby blocking the actions of endogenous or exogenous β-adrenergic agonists. β-Adrenergic antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches and anxiety.
bronchoconstrictor agent  A drug which causes a narrowing of the lumen of a bronchus or bronchiole.
antihypertensive agent  Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
ChEBI Ontology
Outgoing Relation(s)
2-O-acetyl-1-O-octadecyl-sn-glycero-3-phosphocholine (CHEBI:52450) has role antihypertensive agent (CHEBI:35674)
2-O-acetyl-1-O-octadecyl-sn-glycero-3-phosphocholine (CHEBI:52450) has role bronchoconstrictor agent (CHEBI:50141)
2-O-acetyl-1-O-octadecyl-sn-glycero-3-phosphocholine (CHEBI:52450) has role hematologic agent (CHEBI:50248)
2-O-acetyl-1-O-octadecyl-sn-glycero-3-phosphocholine (CHEBI:52450) has role vasodilator agent (CHEBI:35620)
2-O-acetyl-1-O-octadecyl-sn-glycero-3-phosphocholine (CHEBI:52450) has role β-adrenergic antagonist (CHEBI:35530)
2-O-acetyl-1-O-octadecyl-sn-glycero-3-phosphocholine (CHEBI:52450) is a 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine (CHEBI:36707)
IUPAC Names 
(2RR)-2-acetoxy-3-(octadecyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate
(2R)-2-acetoxy-3-(octadecyloxy)propyl 2-(trimethylammonio)ethyl phosphate
Synonyms  Source
platelet activating factorChEBI
PAFSUBMITTER
PAF-acetherSUBMITTER
AGEPCSUBMITTER
acetyl-glyceryl-ether-phosphorylcholineSUBMITTER
1-O-octadecyl 2-O-acetyl sn-glycero-3-phosphorylcholineChemIDplus
UniProt Name  Source
1-O-octadecyl-2-acetyl-sn-glycero-3-phosphocholineUniProt
Manual XrefsDatabases
DB02261DrugBank
LMGP01020094LIPID MAPS
LMGP01020094LIPID MAPS
Platelet-activating_factorWikipedia
Registry NumbersSources
Beilstein:5364572Beilstein
Reaxys:5364572Reaxys
Reaxys:5364572Reaxys
CAS:74389-69-8ChemIDplus
CAS:74389-69-8ChemIDplus