ChemFOnt: Showing chemical card for PGP(16:1(9Z)/18:2(9Z,12Z)) (CFc000008408)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:08 UTC

Chemfont ID

CFc000008408

Molecule Identification

Common Name

PGP(16:1(9Z)/18:2(9Z,12Z))

Definition

PGP(16:1(9Z)/18:2(9Z,12Z)) is a phosphatidylglycerolphosphate or glycerophospholipid (PGP or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site followed by another phosphate moiety. 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. PGP(16:1(9Z)/18:2(9Z,12Z)), in particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The palmitoleic acid moiety is derived from animal fats and vegetable oils, while the linoleic acid moiety is derived from seed oils. Phosphatidylglycerolphosphate 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 Phosphatidylglycerolphosphate increases during fetal development. Phosphatidylglycerolphosphate 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. PGPs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PGP also serves as a precursor for the synthesis of cardiolipin. PGP is synthesized from CDP-diacylglycerol and glycerol-3-phosphate.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid	Lipid Annotator, HMDB
PGP(16:1(9Z)/18:2(9Z,12Z))	Lipid Annotator
PGP(16:1/18:2)	Lipid Annotator, HMDB
1-palmitoleoyl-2-linoleoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)	Lipid Annotator, HMDB
1-(9Z-hexadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)	Lipid Annotator, HMDB
PGP(34:3)	Lipid Annotator, HMDB
PGP(16:1n7/18:2n6)	HMDB
PGP(16:1W7/18:2W6)	HMDB

Chemical Formula

C₄₀H₇₄O₁₃P₂

Average Molecular Weight

824.9553

Monoisotopic Molecular Weight

824.460465478

IUPAC Name

[(2S)-3-({[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid

Traditional Name

(2S)-3-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid

CAS Registry Number

None

SMILES

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

InChI Identifier

InChI=1S/C40H74O13P2/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-40(43)53-38(36-52-55(47,48)51-34-37(41)33-50-54(44,45)46)35-49-39(42)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h11,13-14,16-18,37-38,41H,3-10,12,15,19-36H2,1-2H3,(H,47,48)(H2,44,45,46)/b13-11-,16-14-,18-17-/t37-,38+/m0/s1

InChI Key

NIARWGBRSLNJEA-IEVJMAIKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylglycerophosphates. These are glycerophosphoglycerophosphates in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoglycerophosphates

Direct Parent

Phosphatidylglycerophosphates

Alternative Parents

Substituents

Diacylglycerophosphoglycerophosphate
Sn-glycerol-3-phosphate
Fatty acid ester
Monoalkyl phosphate
Dialkyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Organoleptic effect

Touch

Smooth (HMDB: HMDB0013492)

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0013492)
Extracellular (HMDB: HMDB0013492)
Cell membrane (HMDB: HMDB0013492)
Intracellular membrane (HMDB: HMDB0013492)

Tissue

All Tissues (HMDB: HMDB0013492)
All Tissues (HMDB: HMDB0013492)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0013492)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013492)

Source

Endogenous

Endogenous (HMDB: HMDB0013492)

Animal

Animal (HMDB: HMDB0013492)

Exogenous

Food

Food (HMDB: HMDB0013492)

Exogenous (HMDB: HMDB0013492)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0013492)

Biochemical pathway

Metabolic pathway

Lipid metabolism pathway (HMDB: HMDB0013492)

Cellular process

Cell signaling (HMDB: HMDB0013492)

Biochemical process

Lipid transport (HMDB: HMDB0013492)

Role

Biological role

Energy source (HMDB: HMDB0013492)

Industrial application

Food and nutrition

Food additive (HMDB: HMDB0013492)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013492)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00096 g/L	ALOGPS
logP	6.95	ALOGPS
logP	10.62	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	1.35	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	195.35 Å²	ChemAxon
Rotatable Bond Count	41	ChemAxon
Refractivity	218.73 m³·mol⁻¹	ChemAxon
Polarizability	91.18 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

HMDB0013492

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029492

KNApSAcK ID

Not Available

Chemspider ID

35032671

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481812

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for PGP(16:1(9Z)/18:2(9Z,12Z)) (CFc000008408)

MOL for CFc000008408 (PGP(16:1(9Z)/18:2(9Z,12Z)))

3D MOL for CFc000008408 (PGP(16:1(9Z)/18:2(9Z,12Z)))

3D SDF for CFc000008408 (PGP(16:1(9Z)/18:2(9Z,12Z)))

3D-SDF for CFc000008408 (PGP(16:1(9Z)/18:2(9Z,12Z)))

PDB for CFc000008408 (PGP(16:1(9Z)/18:2(9Z,12Z)))

3D PDB for CFc000008408 (PGP(16:1(9Z)/18:2(9Z,12Z)))

SMILES for CFc000008408 (PGP(16:1(9Z)/18:2(9Z,12Z)))

INCHI for CFc000008408 (PGP(16:1(9Z)/18:2(9Z,12Z)))

Structure for CFc000008408 (PGP(16:1(9Z)/18:2(9Z,12Z)))

3D Structure for CFc000008408 (PGP(16:1(9Z)/18:2(9Z,12Z)))