ChemFOnt: Showing chemical card for PA(O-20:4(5Z,8Z,11Z,14Z)/2:0) (CFc000006790)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:52:52 UTC

Chemfont ID

CFc000006790

Molecule Identification

Common Name

PA(O-20:4(5Z,8Z,11Z,14Z)/2:0)

Definition

PA(O-20:4(5Z,8Z,11Z,14Z)/2:0) 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(O-20:4(5Z,8Z,11Z,14Z)/2:0), in particular, consists of one 5Z,8Z,11Z,14Z-eicosatetraenoyl chain to the C-1 atom, and one acetyl to the C-2 atom. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₅H₄₃O₇P

Average Molecular Weight

486.5785

Monoisotopic Molecular Weight

486.274640242

IUPAC Name

[(2R)-2-(acetyloxy)-3-(icosa-5,8,11,14-tetraen-1-yloxy)propoxy]phosphonic acid

Traditional Name

(2R)-2-(acetyloxy)-3-(icosa-5,8,11,14-tetraen-1-yloxy)propoxyphosphonic acid

CAS Registry Number

None

SMILES

[H][C@@](COCCCCC=CCC=CCC=CCC=CCCCCC)(COP(O)(O)=O)OC(C)=O

InChI Identifier

InChI=1S/C25H43O7P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-30-22-25(32-24(2)26)23-31-33(27,28)29/h7-8,10-11,13-14,16-17,25H,3-6,9,12,15,18-23H2,1-2H3,(H2,27,28,29)/t25-/m1/s1

InChI Key

LTIFQHVEGFEXBJ-RUZDIDTESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-alkyl,2-acylglycerophosphates. These are glycerophosphates in which the O-1 atom of the glycerol is bonded to a fatty acid (saturated or unsaturated) through an ether linkage, and the O-2 atom is bonded to another fatty acid through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

1-alkyl,2-acylglycerophosphates

Alternative Parents

Substituents

1-alkyl,2-acyl-glycerol-3-phosphate
Monoalkyl phosphate
Glycerol ether
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0011156)
Membrane (HMDB: HMDB0011156)

Source

Exogenous

Exogenous (HMDB: HMDB0011156)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0011156)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0012 g/L	ALOGPS
logP	5.89	ALOGPS
logP	6.11	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	1.32	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	137.25 m³·mol⁻¹	ChemAxon
Polarizability	54.43 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027931

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for PA(O-20:4(5Z,8Z,11Z,14Z)/2:0) (CFc000006790)

MOL for CFc000006790 (PA(O-20:4(5Z,8Z,11Z,14Z)/2:0))

3D MOL for CFc000006790 (PA(O-20:4(5Z,8Z,11Z,14Z)/2:0))

3D SDF for CFc000006790 (PA(O-20:4(5Z,8Z,11Z,14Z)/2:0))

3D-SDF for CFc000006790 (PA(O-20:4(5Z,8Z,11Z,14Z)/2:0))

PDB for CFc000006790 (PA(O-20:4(5Z,8Z,11Z,14Z)/2:0))

3D PDB for CFc000006790 (PA(O-20:4(5Z,8Z,11Z,14Z)/2:0))

SMILES for CFc000006790 (PA(O-20:4(5Z,8Z,11Z,14Z)/2:0))

INCHI for CFc000006790 (PA(O-20:4(5Z,8Z,11Z,14Z)/2:0))

Structure for CFc000006790 (PA(O-20:4(5Z,8Z,11Z,14Z)/2:0))

3D Structure for CFc000006790 (PA(O-20:4(5Z,8Z,11Z,14Z)/2:0))