ChemFOnt: Showing chemical card for PG(16:1(9Z)/18:1(9Z)) (CFc000006595)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:52:37 UTC

Chemfont ID

CFc000006595

Molecule Identification

Common Name

PG(16:1(9Z)/18:1(9Z))

Definition

PG(16:1(9Z)/18:1(9Z)) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols 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. PG(16:1(9Z)/18:1(9Z)), in particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of oleic acid at the C-2 position. The palmitoleic acid moiety is derived from animal fats and vegetable oils, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-(9Z-Hexadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-glycerol)	HMDB
1-Palmitoleoyl-2-oleoyl-sn-glycero-3-phosphoglycerol	HMDB
GPG(16:1/18:1)	HMDB
GPG(16:1N7/18:1N9)	HMDB
GPG(16:1W7/18:1W9)	HMDB
GPG(34:2)	HMDB
PG(16:1/18:1)	HMDB
PG(16:1N7/18:1N9)	HMDB
PG(16:1W7/18:1W9)	HMDB
PG(34:2)	HMDB
Phosphatidylglycerol(16:1/18:1)	HMDB
Phosphatidylglycerol(16:1n7/18:1n9)	HMDB
Phosphatidylglycerol(16:1W7/18:1W9)	HMDB
Phosphatidylglycerol(34:2)	HMDB
1-(9Z-Hexadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoglycerol	HMDB
PG(16:1(9Z)/18:1(9Z))	Lipid Annotator

Chemical Formula

C₄₀H₇₅O₁₀P

Average Molecular Weight

746.9913

Monoisotopic Molecular Weight

746.509785132

IUPAC Name

[(2S)-2,3-dihydroxypropoxy][(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid

Traditional Name

(2S)-2,3-dihydroxypropoxy((2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(9Z)-octadec-9-enoyloxy]propoxy)phosphinic acid

CAS Registry Number

None

SMILES

[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC

InChI Identifier

InChI=1S/C40H75O10P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-40(44)50-38(36-49-51(45,46)48-34-37(42)33-41)35-47-39(43)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h14,16-18,37-38,41-42H,3-13,15,19-36H2,1-2H3,(H,45,46)/b16-14-,18-17-/t37-,38+/m0/s1

InChI Key

VCYYBLIRAQBPTM-GDNUZSQHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoglycerols

Direct Parent

Phosphatidylglycerols

Alternative Parents

Substituents

1,2-diacylglycerophosphoglycerol
Fatty acid ester
Dialkyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Alcohol
Organic oxygen compound
Primary alcohol
Carbonyl group
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Diacylglycerophosphoglycerols (LMGP04010902 )

Functional Ontology

Physiological effect

Organoleptic effect

Touch

Smooth (HMDB: HMDB0010589)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 20671299)

Cellular substructure

Membrane (HMDB: HMDB0010589)
Extracellular (HMDB: HMDB0010589)
Cell membrane (HMDB: HMDB0010589)
Intracellular membrane (HMDB: HMDB0010589)

Tissue

All Tissues (HMDB: HMDB0010589)
All Tissues (HMDB: HMDB0010589)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0010589)

Source

Endogenous

Endogenous (HMDB: HMDB0010589)

Animal

Animal (HMDB: HMDB0010589)

Exogenous

Food

Food (HMDB: HMDB0010589)

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)

Exogenous (HMDB: HMDB0010589)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0010589)

Biochemical pathway

Metabolic pathway

Lipid metabolism pathway (HMDB: HMDB0010589)

Cellular process

Cell signaling (HMDB: HMDB0010589)

Biochemical process

Lipid transport (HMDB: HMDB0010589)

Role

Biological role

Energy source (HMDB: HMDB0010589)

Industrial application

Food and nutrition

Food additive (HMDB: HMDB0010589)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0010589)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0001 g/L	ALOGPS
logP	8.02	ALOGPS
logP	11.1	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	1.89	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	148.82 Å²	ChemAxon
Rotatable Bond Count	40	ChemAxon
Refractivity	206.74 m³·mol⁻¹	ChemAxon
Polarizability	88.95 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

HMDB0010589

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027739

KNApSAcK ID

Not Available

Chemspider ID

24768088

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52927167

PDB ID

Not Available

ChEBI ID

89093

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for PG(16:1(9Z)/18:1(9Z)) (CFc000006595)

MOL for CFc000006595 (PG(16:1(9Z)/18:1(9Z)))

3D MOL for CFc000006595 (PG(16:1(9Z)/18:1(9Z)))

3D SDF for CFc000006595 (PG(16:1(9Z)/18:1(9Z)))

3D-SDF for CFc000006595 (PG(16:1(9Z)/18:1(9Z)))

PDB for CFc000006595 (PG(16:1(9Z)/18:1(9Z)))

3D PDB for CFc000006595 (PG(16:1(9Z)/18:1(9Z)))

SMILES for CFc000006595 (PG(16:1(9Z)/18:1(9Z)))

INCHI for CFc000006595 (PG(16:1(9Z)/18:1(9Z)))

Structure for CFc000006595 (PG(16:1(9Z)/18:1(9Z)))

3D Structure for CFc000006595 (PG(16:1(9Z)/18:1(9Z)))