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

ChEBI IDCHEBI:44811
ChEBI Name2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine
Stars
ASCII Name2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine
DefinitionA 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.
Last Modified4 October 2013
DownloadsMolfile
FormulaC26H54NO7P
Net Charge0
Average Mass523.692
Monoisotopic Mass523.36379
SMILESCCCCCCCCCCCCCCCCOC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(C)=O
InChIInChI=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
InChIKeyHVAUUPRFYPCOCA-AREMUKBSSA-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:
antihypertensive agent  Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
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.
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.
ChEBI Ontology
Outgoing Relation(s)
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) has role β-adrenergic antagonist (CHEBI:35530)
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  Source
1-hexadecyl-2-acetyl-sn-glycero-3-phosphocholineLIPID MAPS
1-O-hexadecyl-2-O-acetyl-sn-glyceryl-3-phosphorylcholineChemIDplus
1-O-hexadecyl-2-O-acetyl-sn-glycero-3-phosophocholineChemIDplus
platelet-activating factor C16ChemIDplus
1-O-hexadecyl-platelet-activating factorChemIDplus
1-O-hexadecyl-2-acetyl-sn-glyceryl-3-phosphorylcholineChemIDplus
UniProt Name  Source
1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholineUniProt
Manual XrefsDatabases
PFSPDBeChem
LMGP01020046LIPID MAPS
Platelet-activating_factorWikipedia
DB02261DrugBank
Registry NumbersSources
Reaxys:3574588Reaxys
CAS:74389-68-7ChemIDplus
Citations