ChemFOnt: Showing chemical card for PGP(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (CFc000096913)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:09:54 UTC

Chemfont ID

CFc000096913

Molecule Identification

Common Name

PGP(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))

Definition

PGP(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a phosphatidylglycerophosphate (PGP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site followed by another phosphate moiety. 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 (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 cardiolipin synthesis. As is the case with diacylglycerols, phosphatidylglycerophosphates can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PGP(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of clupanodonic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. They are synthesized by the addition of glycerol 3-phosphate to a CDP-diacylglycerol. In turn, PGPs are dephosphorylated to phosphatidylglycerols (PGs). 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Clupanodonoyl-2-docosahexaenoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)	HMDB
PGP(22:5/22:6)	HMDB
PGP(22:5n3/22:6n3)	HMDB
PGP(22:5W3/22:6W3)	HMDB
PGP(44:11)	HMDB
1-Docosapentaenoyl-2-docosahexaenoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)	HMDB
1-(7Z,10Z,13Z,16Z,19Z-Docosapentaenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)	HMDB
3-sn-Phosphatidyl-1'-sn-glycerol 3'-phosphoric acid	HMDB
[(2S)-3-({[(2R)-2-[(4Z,7Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonate	HMDB
1-clupanodonoyl-2-docosahexaenoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)	SMPDB, HMDB
PGP(22:5/22:6)	SMPDB, HMDB
PGP(22:5n3/22:6n3)	SMPDB, HMDB
PGP(22:5w3/22:6w3)	SMPDB, HMDB
PGP(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))	SMPDB

Chemical Formula

C₅₀H₇₈O₁₃P₂

Average Molecular Weight

949.109

Monoisotopic Molecular Weight

948.491766568

IUPAC Name

[(2S)-3-({[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid

Traditional Name

(2S)-3-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C50H78O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-39-41-49(52)59-45-48(46-62-65(57,58)61-44-47(51)43-60-64(54,55)56)63-50(53)42-40-38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h5-8,11-14,17-20,23-26,29-32,36,38,47-48,51H,3-4,9-10,15-16,21-22,27-28,33-35,37,39-46H2,1-2H3,(H,57,58)(H2,54,55,56)/b7-5-,8-6-,13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,31-29-,32-30-,38-36-/t47-,48+/m0/s1

InChI Key

MBMWGIKVYGDMDX-QFRULVDMSA-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

Not Available

Endogenous (HMDB: HMDB0116504)

Process

Naturally occurring process

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0011 g/L	ALOGPS
logP	7.46	ALOGPS
logP	12.17	ChemAxon
logS	-6	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	43	ChemAxon
Refractivity	273.68 m³·mol⁻¹	ChemAxon
Polarizability	102.4 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

HMDB0116504

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

74878216

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131823159

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for PGP(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (CFc000096913)

MOL for CFc000096913 (PGP(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D MOL for CFc000096913 (PGP(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D SDF for CFc000096913 (PGP(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D-SDF for CFc000096913 (PGP(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

PDB for CFc000096913 (PGP(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D PDB for CFc000096913 (PGP(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

SMILES for CFc000096913 (PGP(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

INCHI for CFc000096913 (PGP(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

Structure for CFc000096913 (PGP(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D Structure for CFc000096913 (PGP(22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))