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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-02-24 01:29:40 UTC
Update Date2019-11-21 18:23:05 UTC
HMDB IDHMDB0062195
Secondary Accession Numbers
  • HMDB62195
Metabolite Identification
Common NamePlatelet-activating factor
DescriptionPlatelet-activating factor, also known as PAF and PC(O-16:0/2:0), is a ubiquitous, potent phospholipid activator and mediator of inflammation that has an important role in the pathogenesis of inflammatory disorders and cardiovascular disease. PAF is able to cause platelet aggregation and anaphylaxis. PAF is synthesized continuously in low quantities in many different types of cells, but especially those involved in host defence, such as macrophages, monocytes, granulocytes, neutrophils, platelets, and endothelial cells. Platelet-activating factor receptor (PAFR) is a G-protein coupled receptor (GPCR) located on the cell membranes of a variety of cells. Once bound to its receptor, PAF mobilizes calcium and activates a wide range of signalling pathways (e.g. phospholipase C-mediated signalling (PMID: 26616844 ).
Structure
Data?1574360583
Synonyms
ValueSource
(R)-7-(Acetyloxy)-4-hydroxy-N,N,N-trimethyl-3,5,9-trioxa-4-phosphapentacosan-1-aminium hydroxide inner salt 4-oxideChEBI
1-Hexadecyl-2-acetyl-sn-glycero-3-phosphocholineChEBI
1-O-Hexadecyl pafChEBI
1-O-Hexadecyl-2-acetyl-sn-glycero-3-phosphocholineChEBI
1-O-Hexadecyl-2-acetyl-sn-glyceryl-3-phosphorylcholineChEBI
1-O-Hexadecyl-2-O-acetyl-sn-glycero-3-phosophocholineChEBI
1-O-Hexadecyl-2-O-acetyl-sn-glyceryl-3-phosphorylcholineChEBI
1-O-Hexadecyl-platelet-activating factorChEBI
C16 PAFChEBI
C16-PAFChEBI
C16:0 PAFChEBI
PAFChEBI
Platelet activating factorChEBI
Platelet-activating factorChEBI
Platelet-activating factor C16ChEBI
1-Hexadecyl-2-acetyl-glycerophosphocholineHMDB
APRLHMDB
Hexadecyl-paf-acetherHMDB
1-Hexadecyl-2-acetyl-glycero-3-phosphocholineHMDB
HD-PAFHMDB
PAF-16 CPDHMDB
HAG-PCHMDB
HAGPCHMDB
Antihypertensive polar renomedullary lipidHMDB
Aggregating factor, plateletMeSH
PAF-acetherMeSH
Phosphorylcholine, acetyl glyceryl etherMeSH
Platelet-activating substanceMeSH
AGEPCMeSH
Platelet activating substanceMeSH
Platelet aggregation enhancing factorMeSH
Factor, platelet activatingMeSH
PAF acetherMeSH
Thrombocyte aggregating activityMeSH
1 Alkyl 2 acetyl sn glycerophosphocholineMeSH
1-Alkyl-2-acetyl-sn-glycerophosphocholineMeSH
Acetyl glyceryl ether phosphorylcholineMeSH
Platelet aggregating factorMeSH
1-Hexadecyl-2-acetyl-GPCHMDB
1-Hexadecyl-2-acetyl-sn-glycero-phosphatidylcholineHMDB
1-O-Hexadecyl-2-O-acetyl-sn-glycero-3-phosphocholineHMDB
1-O-Hexadecyl-2-acetyl-sn-glycerophosphocholineHMDB
Acetyl-glyceryl-ether-phosphorylcholineHMDB
Blood platelet-activating factorHMDB
Blood platelet-activating factor acetherHMDB
C16-PAF acetherHMDB
GPC(16:0/2:0)HMDB
GPC(18:0)HMDB
GPC(O-16:0/2:0)HMDB
GPCho(16:0/2:0)HMDB
GPCho(18:0)HMDB
GPCho(O-16:0/2:0)HMDB
PAF 16HMDB
PAF C 16HMDB
PC(16:0/2:0)HMDB
PC(18:0)HMDB
PC(O-16:0/2:0)HMDB
Phosphatidylcholine(16:0/2:0)HMDB
Phosphatidylcholine(18:0)HMDB
Phosphatidylcholine(O-16:0/2:0)HMDB
Platelet-activating factor (1-O-hexadecyl)HMDB
Platelet-activating factor acetherHMDB
Chemical FormulaC26H54NO7P
Average Molecular Weight523.6832
Monoisotopic Molecular Weight523.363789599
IUPAC Name(2-{[(S)-((2R)-2-(acetyloxy)-3-(hexadecyloxy)propyl phosphono)]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(S)-((2R)-2-(acetyloxy)-3-(hexadecyloxy)propyl phosphono)]oxy}ethyl)trimethylazanium
CAS Registry Number74389-68-7
SMILES
CCCCCCCCCCCCCCCCOC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(C)=O
InChI Identifier
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
InChI KeyHVAUUPRFYPCOCA-AREMUKBSSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-alkyl,2-acetylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acetyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-alkyl,2-acetylglycero-3-phosphocholines
Alternative Parents
Substituents
  • 1-alkyl,2-acetylglycero-3-phosphocholine
  • Phosphocholine
  • Glycerol ether
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00022 g/lALOGPS
LogP2.71ALOGPS
Predicted Properties
PropertyValueSource
logP2.71ALOGPS
logP2.01ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area94.12 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity151.67 m³·mol⁻¹ChemAxon
Polarizability62.86 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-7920100000-1c445dd863672863393fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-1912020000-cd0b0948116f9c94f643Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02261
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID97241
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPlatelet-activating_factor
METLIN IDNot Available
PubChem Compound108156
PDB IDNot Available
ChEBI ID44811
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Kelesidis T, Papakonstantinou V, Detopoulou P, Fragopoulou E, Chini M, Lazanas MC, Antonopoulou S: The Role of Platelet-Activating Factor in Chronic Inflammation, Immune Activation, and Comorbidities Associated with HIV Infection. AIDS Rev. 2015 Oct-Dec;17(4):191-201. [PubMed:26616844 ]
  7. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.