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

Default Structure
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:
bronchoconstrictor agent  A drug which causes a narrowing of the lumen of a bronchus or bronchiole.
vasodilator agent  A drug used to cause dilation of the blood vessels.
antihypertensive agent  Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
hematologic agent  Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.
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.
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 
(2R)-2-acetoxy-3-(octadecyloxy)propyl 2-(trimethylammonio)ethyl phosphate
(2RR)-2-acetoxy-3-(octadecyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate
Synonyms  Source
1-0-octadecyl 2-0-acetyl sn-glycero-3-phosphorylcholineChemIDplus
1-O-octadecyl-2-acetyl-sn-glyceryl-3-phosphorylcholineChemIDplus
1-O-octadecyl-2-O-acetyl-sn-glycero-3-phosphocholineChEBI
1-O-octadecyl 2-O-acetyl sn-glycero-3-phosphorylcholineChemIDplus
1-O-octadecyl-2-O-acetyl-sn-glyceryl-3-phosphorylcholineChemIDplus
1-O-octadecyl-PAFChEBI
UniProt Name  Source
1-O-octadecyl-2-acetyl-sn-glycero-3-phosphocholineUniProt
Manual XrefsDatabases
DB02261DrugBank
LMGP01020094LIPID MAPS
LMGP01020094LIPID MAPS
Platelet-activating_factorWikipedia
Registry NumbersSources
Reaxys:5364572Reaxys
Reaxys:5364572Reaxys
Beilstein:5364572Beilstein
CAS:74389-69-8ChemIDplus
CAS:74389-69-8ChemIDplus