Showing metabocard for PC(O-16:0/2:0) (BMDB0062818)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-08-29 17:12:06 UTC
Update Date2020-06-04 19:24:24 UTC
BMDB IDBMDB0062818
Secondary Accession Numbers
  • BMDB62818
Metabolite Identification
Common NamePC(O-16:0/2:0)
Description2-acetyl-1-alkyl-sn-glycero-3-phosphocholine, also known as 1-O-hexadecyl paf or 1-O-hexadecyl-platelet-activating factor, 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. Thus, 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine is considered to be a glycerophosphocholine lipid molecule. 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
StatusExpected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-7920100000-1c445dd863672863393fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-1912020000-cd0b0948116f9c94f643View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000090000-70514fe85c8e3c0890eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000090000-70514fe85c8e3c0890eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-5001920000-fed72cb85f07c7623fbeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-2000090000-17c9524659f9c78dd8aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000010000-a0c661c1c6e6ea6501ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-e49acc579337dc9681c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000090000-cb20f2bc7d50322718cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000090000-cb20f2bc7d50322718cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0089-1913460000-d473e16780d273cab196View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0062195
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.