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

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ChEBI Name 2-O-acetyl-1-O-octadecyl-sn-glycero-3-phosphocholine
ChEBI ID CHEBI:52450
ChEBI ASCII Name 2-O-acetyl-1-O-octadecyl-sn-glycero-3-phosphocholine
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Bijay
Lucila Aimo
Secondary ChEBI IDs CHEBI:26164, CHEBI:52390, CHEBI:75217
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Formulae C28H58NO7P
C28H58NO7P
Net Charge 0
Average Mass 551.737
Monoisotopic Mass 551.395
InChI InChI=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
InChIKey ZXCIEWBDUAPBJF-MUUNZHRXSA-N
SMILES P(OC[C@@H](COCCCCCCCCCCCCCCCCCC)OC(C)=O)(=O)(OCC[N+](C)(C)C)[O-]
Roles Classification
Biological Role(s): beta-adrenergic antagonist
An agent that binds to but does not activate beta-adrenergic receptors thereby blocking the actions of endogenous or exogenous beta-adrenergic agonists. beta-Adrenergic antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches and anxiety.
Application(s): beta-adrenergic antagonist
An agent that binds to but does not activate beta-adrenergic receptors thereby blocking the actions of endogenous or exogenous beta-adrenergic agonists. beta-Adrenergic antagonists are used for treatment of hypertension, cardiac arrhythmias, angina pectoris, glaucoma, migraine headaches and anxiety.
antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
vasodilator agent
A drug used to cause dilation of the blood vessels.
bronchoconstrictor agent
A drug which causes a narrowing of the lumen of a bronchus or bronchiole.
hematologic agent
Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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) 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) 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 Sources
(−)-1-O-octadeyl-2-O-acetyl-sn-glycerylphosphocholine ChEBI
(R)-7-(acetyloxy)-4-hydroxy-N,N,N-trimethyl-3,5,9-trioxa-4-phosphaheptaconasan-1-aminium hydroxide inner salt 4-oxide ChEBI
1-0-octadecyl 2-0-acetyl sn-glycero-3-phosphorylcholine ChemIDplus
1-O-octadecyl 2-O-acetyl sn-glycero-3-phosphorylcholine ChemIDplus
1-O-octadecyl-2-acetyl-sn-glycero-3-phosphocholine UniProt
1-O-octadecyl-2-acetyl-sn-glyceryl-3-phosphorylcholine ChemIDplus
1-O-octadecyl-2-O-acetyl-sn-glycero-3-phosphocholine ChEBI
1-O-octadecyl-2-O-acetyl-sn-glyceryl-3-phosphorylcholine ChemIDplus
1-O-octadecyl-PAF ChEBI
1-O-Octadecyl-platelet-activating factor ChemIDplus
1-O-octadecyl-platelet-activating factor ChemIDplus
1-O-Stearoyl-2-acetyl-sn-glyceryl-3-phosphorylcholine ChemIDplus
1-O-Stearyl-2-acetyl-sn-glyceryl-3-phosphorylcholine ChemIDplus
1-octadecyl-2-acetyl-sn-glycero-3-phosphocholine LIPID MAPS
acetyl-glyceryl-ether-phosphorylcholine SUBMITTER
AGEPC SUBMITTER
blood platelet activating factor-acether LIPID MAPS
Blood platelet activating factor-aether ChemIDplus
Blood platelet-activating factor ChemIDplus
Blood platelet-activating factor ChemIDplus
C18-Paf ChemIDplus
C18-PAF ChEBI
C18-PAF-acether LIPID MAPS
C18:0 PAF ChEBI
PAF SUBMITTER
PAF acether LIPID MAPS
PAF-acether SUBMITTER
PC(O-18:0/2:0) SUBMITTER
PC(O-18:0/2:0) LIPID MAPS
phosphatidylcholine (O-18:0/2:0) SUBMITTER
platelet activating factor ChEBI
platelet activating factor-acether LIPID MAPS
Platelet-activating factor ChemIDplus
platelet-activating factor LIPID MAPS
Ro 14-8161 LIPID MAPS
Manual Xrefs Databases
DB02261 DrugBank
LMGP01020094 LIPID MAPS
LMGP01020094 LIPID MAPS
Platelet-activating_factor Wikipedia
View more database links
Registry Numbers Types Sources
5364572 Reaxys Registry Number Reaxys
5364572 Beilstein Registry Number Beilstein
5364572 Reaxys Registry Number Reaxys
74389-69-8 CAS Registry Number ChemIDplus
74389-69-8 CAS Registry Number ChemIDplus
Last Modified
02 December 2016