FComEx: PA(16:0/16:0) (PC000442)

Record Information

Version

1.0

Creation date

2015-10-09 22:30:45 UTC

Update date

2017-01-19 02:36:24 UTC

FoodComEx ID

PC000442

FoodDB Record

FDB022175

Chemical Information

Name

PA(16:0/16:0)

Description

PA(16:0/16:0) is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(16:0/16:0), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. Indeed, the concentration of phosphatidic acids is often over-estimated in tissues and biofluids as it can arise by inadvertent enzymatic hydrolysis during inappropriate storage or extraction conditions during analysis. The main biosynthetic route of phosphatidic acid in animal tissues involves sequential acylation of alpha-glycerophosphate by acyl-coA derivatives of fatty acids. PAs are biologically active lipids that can stimulate a large range of responses in many different cell types, such as platelet aggregation, smooth muscle contraction, in vivo vasoactive effects, chemotaxis, expression of adhesion molecules, increased tight junction permeability of endothelial cells, induction of stress fibres, modulation of cardiac contractility, and many others. Diacylglycerols (DAGs) can be converted to PAs by DAG kinases and indirect evidence supports the notion that PAs alter the excitability of neurons. Phospholipase Ds (PLDs), which catalyze the conversion of glycerolphospholipids, particularly phosphatidylcholine, to PAs and the conversion of N-arachidonoyl-phosphatidylethanolamine (NAPE) to anandamide and PAs are activated by several inflammatory mediators including bradykinin, ATP and glutamate. PAs activate downstream signaling pathways such as PKCs and mitogen-activated protein kinases (MAPKs), which are linked to an increase in sensitivity of sensory neurons either during inflammation or in chronic pain models. Circumstantial evidence that PAs are converted to DAGs. (PMID: 12618218, 16185776). [HMDB]

CAS Number

7091-44-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,2-Di-O-palmitoyl-3-sn-glyceryl-O-orate	HMDB
1,2-Di-O-palmitoyl-3-sn-glyceryl-O-oric acid	HMDB
1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphorate	hmdb
1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphoric acid	hmdb
1,2-Dihexadecanoyl-rac-atidic acid	HMDB
1,2-dihexadecanoyl-rac-phosphatidic acid	hmdb
1,2-Dipalmitoyl-3-sn-atidate	Generator
1,2-Dipalmitoyl-3-sn-atidic acid	ChEBI
1,2-Dipalmitoyl-3-sn-phosphatidate	hmdb
1,2-Dipalmitoyl-3-sn-phosphatidic acid	hmdb
1,2-Dipalmitoyl-sn-glycerol 3-ate	HMDB
1,2-Dipalmitoyl-sn-glycerol 3-phosphate	hmdb
1,2-Dipalmitoyl-sn-glycerol-3-ate	ChEBI
1,2-Dipalmitoyl-sn-glycerol-3-ic acid	Generator
1,2-Dipalmitoyl-sn-glycerol-3-orate	Generator
1,2-Dipalmitoyl-sn-glycerol-3-oric acid	ChEBI
1,2-Dipalmitoyl-sn-glycerol-3-phosphorate	hmdb
1,2-Dipalmitoyl-sn-glycerol-3-phosphoric acid	hmdb
Atidate(16:0/16:0)	Generator
Atidate(32:0)	Generator
Atidic acid(16:0/16:0)	ChEBI
Atidic acid(32:0)	ChEBI
Dipalmitoyl atidate	Generator
Dipalmitoyl atidic acid	ChEBI
Dipalmitoyl-L-a-atidate	HMDB
Dipalmitoyl-L-a-atidic acid	HMDB
Dipalmitoyl-L-a-phosphatidate	hmdb
Dipalmitoyl-L-a-phosphatidic acid	hmdb
Dipalmitoyl-L-alpha-atidate	HMDB
Dipalmitoyl-L-alpha-atidic acid	HMDB
Dipalmitoyl-L-alpha-phosphatidate	hmdb
Dipalmitoyl-L-alpha-phosphatidic acid	hmdb
Dipalmitoylatidate	HMDB
Dipalmitoylatidic acid	HMDB
Dipalmitoylphosphatidate	hmdb
Dipalmitoylphosphatidic acid	hmdb
L-a-Dipalmitoyl-atidate	HMDB
L-a-Dipalmitoyl-atidic acid	HMDB
L-a-Dipalmitoyl-phosphatidate	hmdb
L-a-Dipalmitoyl-phosphatidic acid	hmdb
L-a-Dipalmitoylatidate	HMDB
L-a-Dipalmitoylatidic acid	HMDB
L-a-Dipalmitoylphosphatidate	hmdb
L-a-Dipalmitoylphosphatidic acid	hmdb
L-alpha-Dipalmitoyl-atidate	HMDB
L-alpha-Dipalmitoyl-atidic acid	HMDB
L-alpha-Dipalmitoyl-phosphatidate	hmdb
L-alpha-Dipalmitoyl-phosphatidic acid	hmdb
L-alpha-Dipalmitoylatidate	HMDB
L-alpha-Dipalmitoylatidic acid	HMDB
L-alpha-Dipalmitoylphosphatidate	hmdb
L-alpha-Dipalmitoylphosphatidic acid	hmdb
PA(32:0)	hmdb
Phosphatidic acid(16:0/16:0)	hmdb
Phosphatidic acid(32:0)	hmdb

Chemical Formula

C35H69O8P

IUPAC name

[(2R)-2,3-bis(hexadecanoyloxy)propoxy]phosphonic acid

InChI Identifier

InChI=1S/C35H69O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(36)41-31-33(32-42-44(38,39)40)43-35(37)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33H,3-32H2,1-2H3,(H2,38,39,40)/t33-/m1/s1

InChI Key

PORPENFLTBBHSG-MGBGTMOVSA-N

Isomeric SMILES

[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC

Average Molecular Weight

648.903

Monoisotopic Molecular Weight

648.47300618

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2-diacylglycerol-3-phosphates. These are glycerol-3-phosphates in which the glycerol moiety is bonded to two aliphatic chains through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

1,2-diacylglycerol-3-phosphates

Alternative Parents

Substituents

1,2-diacylglycerol-3-phosphate
Fatty acid ester
Monoalkyl phosphate
Dicarboxylic acid or derivatives
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Carboxylic acid ester
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1-acyl-2-hexadecanoyl-sn-glycero-3-phosphate (CHEBI:73246 )
Diacylglycerophosphates (LMGP10010027 )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	Not Available
Experimental Water Solubility	Not Available
Melting Point	Not Available

Foods of Origin

Food	Content Range	Average	Reference
Food			Reference

Production Data

Production Method

commercial

Production Method Reference

Not Available

Production Method Reference File

Not Available

Quantity Available

Production upon request, up to 200 mg

Delivery Time

Not Available

Storage Form

solid

Storage Conditions

-80°C

Stability

Not Available

Purity

Not Available

Spectra

Spectral Data Upon Request

Not Available

Provider Information

Contact Name	Contact Institution	Contact Email
Rosa Vazquez Fresno		vazquezf@ualberta.ca

Commercial Vendors

Not Available

PA(16:0/16:0) (PC000442)

Structure for FDB022175 (PA(16:0/16:0))