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

Default Structure
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:
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-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-O-hexadecyl-2-acetyl-sn-glyceryl-3-phosphorylcholineChemIDplus
1-O-hexadecyl-2-O-acetyl-sn-glycero-3-phosophocholineChemIDplus
1-O-hexadecyl-2-O-acetyl-sn-glyceryl-3-phosphorylcholineChemIDplus
1-O-hexadecyl PAFChEBI
1-O-hexadecyl-platelet-activating factorChemIDplus
1-hexadecyl-2-acetyl-sn-glycero-3-phosphocholineLIPID MAPS
UniProt Name  Source
1-O-hexadecyl-2-acetyl-sn-glycero-3-phosphocholineUniProt
Manual XrefsDatabases
DB02261DrugBank
LMGP01020046LIPID MAPS
PFSPDBeChem
Platelet-activating_factorWikipedia
Registry NumbersSources
Reaxys:3574588Reaxys
CAS:74389-68-7ChemIDplus
Citations