MiMeDB: Showing metabocard for 2-O-Acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine (MMDBc0047890)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 15:47:45 UTC

Update Date

2024-10-11 04:17:58 UTC

Metabolite ID

MMDBc0047890

Metabolite Identification

Common Name

2-O-Acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine

Description

2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine, also known as platelet-activating factor, 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(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	ChEBI
1-O-Hexadecyl paf	ChEBI
1-O-Hexadecyl-2-acetyl-sn-glycero-3-phosphocholine	ChEBI
1-O-Hexadecyl-2-acetyl-sn-glyceryl-3-phosphorylcholine	ChEBI
1-O-Hexadecyl-2-O-acetyl-sn-glycero-3-phosophocholine	ChEBI
1-O-Hexadecyl-2-O-acetyl-sn-glyceryl-3-phosphorylcholine	ChEBI
1-O-Hexadecyl-platelet-activating factor	ChEBI
C16 PAF	ChEBI
C16-PAF	ChEBI
C16:0 PAF	ChEBI
PAF	ChEBI
Platelet activating factor	ChEBI
Platelet-activating factor	ChEBI
Platelet-activating factor C16	ChEBI
1-Hexadecyl-2-acetyl-glycerophosphocholine	HMDB
APRL	HMDB
Hexadecyl-paf-acether	HMDB
1-Hexadecyl-2-acetyl-glycero-3-phosphocholine	HMDB
HD-PAF	HMDB
PAF-16 CPD	HMDB
HAG-PC	HMDB
HAGPC	HMDB
Antihypertensive polar renomedullary lipid	HMDB
Aggregating factor, platelet	MeSH
PAF-acether	MeSH
Phosphorylcholine, acetyl glyceryl ether	MeSH
Platelet-activating substance	MeSH
AGEPC	MeSH
Platelet activating substance	MeSH
Platelet aggregation enhancing factor	MeSH
Factor, platelet activating	MeSH
PAF acether	MeSH
Thrombocyte aggregating activity	MeSH
1 Alkyl 2 acetyl sn glycerophosphocholine	MeSH
1-Alkyl-2-acetyl-sn-glycerophosphocholine	MeSH
Acetyl glyceryl ether phosphorylcholine	MeSH
Platelet aggregating factor	MeSH
1-Hexadecyl-2-acetyl-GPC	HMDB
1-Hexadecyl-2-acetyl-sn-glycero-phosphatidylcholine	HMDB
1-O-Hexadecyl-2-O-acetyl-sn-glycero-3-phosphocholine	HMDB
1-O-Hexadecyl-2-acetyl-sn-glycerophosphocholine	HMDB
Acetyl-glyceryl-ether-phosphorylcholine	HMDB
Blood platelet-activating factor	HMDB
Blood platelet-activating factor acether	HMDB
C16-PAF acether	HMDB
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 16	HMDB
PAF C 16	HMDB
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 acether	HMDB

Molecular Formula

C₂₆H₅₄NO₇P

Average Mass

523.6832

Monoisotopic Mass

523.363789599

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

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 Key

HVAUUPRFYPCOCA-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

1-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 Framework

Aliphatic acyclic compounds

External Descriptors

2-acetyl-1-alkyl-sn-glycero-3-phosphocholine (CHEBI:44811 )
1-alkyl,2-acylglycerophosphocholines (LMGP01020046 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0062195

DrugBank ID

DB02261

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

97241

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Platelet-activating_factor

METLIN ID

Not Available

PubChem Compound

108156

PDB ID

Not Available

ChEBI ID

44811

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. doi: 10.1016/0092-8674(95)90409-3. [PubMed:7834746 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
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. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
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. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
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 ]
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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.

Showing metabocard for 2-O-Acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine (MMDBc0047890)

MOL for #<Metabolite:0x00007fdb0486b3e8>

3D MOL for #<Metabolite:0x00007fdb0486b3e8>

3D SDF for #<Metabolite:0x00007fdb0486b3e8>

3D-SDF for #<Metabolite:0x00007fdb0486b3e8>

PDB for #<Metabolite:0x00007fdb0486b3e8>

3D PDB for #<Metabolite:0x00007fdb0486b3e8>

SMILES for #<Metabolite:0x00007fdb0486b3e8>

INCHI for #<Metabolite:0x00007fdb0486b3e8>

Structure for #<Metabolite:0x00007fdb0486b3e8>

3D Structure for #<Metabolite:0x00007fdb0486b3e8>