CHEBI:44811 - 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine

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ChEBI Name 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine
ChEBI ID CHEBI:44811
ChEBI ASCII Name 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine
Definition A 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine betaine which has hexadecyl 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.
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Formula C26H54NO7P
Net Charge 0
Average Mass 523.68320
Monoisotopic Mass 523.364
InChI InChI=1S/C26H54NO7P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-21-31-23-26(34-25(2)28)24-33-35(29,30)32-22-20-27(3,4)5/h26H,6-24H2,1-5H3/t26-/m1/s1
InChIKey HVAUUPRFYPCOCA-AREMUKBSSA-N
SMILES CCCCCCCCCCCCCCCCOC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(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.
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.
vasodilator agent
A drug used to cause dilation of the blood vessels.
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ChEBI Ontology
Outgoing 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine (CHEBI:44811) has role β-adrenergic antagonist (CHEBI:35530)
2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine (CHEBI:44811) has role antihypertensive agent (CHEBI:35674)
2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine (CHEBI:44811) has role bronchoconstrictor agent (CHEBI:50141)
2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine (CHEBI:44811) has role hematologic agent (CHEBI:50248)
2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine (CHEBI:44811) has role vasodilator agent (CHEBI:35620)
2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine (CHEBI:44811) is a 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine (CHEBI:36707)
IUPAC Name
(2R)-2-acetoxy-3-(hexadecyloxy)propyl 2-(trimethylammonio)ethyl phosphate
Synonyms Sources
(R)-7-(acetyloxy)-4-hydroxy-N,N,N-trimethyl-3,5,9-trioxa-4-phosphapentacosan-1-aminium hydroxide inner salt 4-oxide ChEBI
1-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine LIPID MAPS
1-O-hexadecyl PAF ChEBI
1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine UniProt
1-O-hexadecyl-2-acetyl-sn-glyceryl-3-phosphorylcholine ChemIDplus
1-O-hexadecyl-2-O-acetyl-sn-glycero-3-phosophocholine ChemIDplus
1-O-hexadecyl-2-O-acetyl-sn-glyceryl-3-phosphorylcholine ChemIDplus
1-O-hexadecyl-platelet-activating factor ChemIDplus
C16 PAF ChEBI
C16-PAF ChEBI
C16:0 PAF ChEBI
PAF ChEBI
Platelet activating factor ChemIDplus
platelet-activating factor ChEBI
platelet-activating factor C16 ChemIDplus
Manual Xrefs Databases
DB02261 DrugBank
LMGP01020046 LIPID MAPS
PFS PDBeChem
Platelet-activating_factor Wikipedia
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Registry Numbers Types Sources
3574588 Reaxys Registry Number Reaxys
74389-68-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
19075994 PubMed citation Europe PMC
19827129 PubMed citation Europe PMC
20431963 PubMed citation Europe PMC
21347278 PubMed citation Europe PMC
21804199 PubMed citation Europe PMC
22924390 PubMed citation Europe PMC
23169529 PubMed citation Europe PMC
Last Modified
04 October 2013