ChemFOnt: Showing chemical card for PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)) (CFc000097011)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:10:03 UTC

Chemfont ID

CFc000097011

Molecule Identification

Common Name

PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z))

Definition

PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)) is a phosphatidylglycerol - 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(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)), in particular, consists of one chain of docosahexaenoic acid at the C-1 position and one chain of mead acid at the C-2 position. 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 (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 cardiolipin synthesis.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Docosahexaenoyl-2-meadoyl-sn-glycero-3-phospho-(1'-glycerol)	HMDB
1-Docosahexaenoyl-2-meadoyl-sn-glycero-3-phosphoglycerol	HMDB
PG(22:6/20:3)	HMDB
PG(22:6N3/20:3N9)	HMDB
PG(22:6W3/20:3W9)	HMDB
PG(42:9)	HMDB
Phosphatidylglycerol(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z))	HMDB
Phosphatidylglycerol(22:6/20:3)	HMDB
Phosphatidylglycerol(22:6n3/20:3n9)	HMDB
Phosphatidylglycerol(22:6W3/20:3W9)	HMDB
Phosphatidylglycerol(42:9)	HMDB
GPG(42:9)	HMDB
GPG(22:6/20:3)	HMDB
1-(4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoyl)-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycero-3-phospho-(1'-glycerol)	HMDB
1-(4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoyl)-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycero-3-phosphoglycerol	HMDB
[(2S)-2,3-Dihydroxypropoxy][(2R)-3-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxy]phosphinate	HMDB
1-docosahexaenoyl-2-meadoyl-sn-glycero-3-phospho-(1'-glycerol)	SMPDB, HMDB
1-docosahexaenoyl-2-meadoyl-sn-glycero-3-phosphoglycerol	SMPDB, HMDB
PG(22:6/20:3)	SMPDB, HMDB
PG(22:6n3/20:3n9)	SMPDB, HMDB
PG(22:6w3/20:3w9)	SMPDB, HMDB
PG(42:9)	SMPDB, HMDB
Phosphatidylglycerol(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z))	SMPDB, HMDB
Phosphatidylglycerol(22:6/20:3)	SMPDB, HMDB
Phosphatidylglycerol(22:6n3/20:3n9)	SMPDB, HMDB
Phosphatidylglycerol(22:6w3/20:3w9)	SMPDB, HMDB
PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z))	SMPDB

Chemical Formula

C₄₈H₇₇O₁₀P

Average Molecular Weight

845.108

Monoisotopic Molecular Weight

844.525435677

IUPAC Name

[(2S)-2,3-dihydroxypropoxy][(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxy]phosphinic acid

Traditional Name

(2S)-2,3-dihydroxypropoxy((2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C48H77O10P/c1-3-5-7-9-11-13-15-17-19-21-22-24-25-27-29-31-33-35-37-39-47(51)55-43-46(44-57-59(53,54)56-42-45(50)41-49)58-48(52)40-38-36-34-32-30-28-26-23-20-18-16-14-12-10-8-6-4-2/h5,7,11,13,17-20,22,24,26-29,32-35,45-46,49-50H,3-4,6,8-10,12,14-16,21,23,25,30-31,36-44H2,1-2H3,(H,53,54)/b7-5-,13-11-,19-17-,20-18-,24-22-,28-26-,29-27-,34-32-,35-33-/t45-,46+/m0/s1

InChI Key

JRLUANGXKLWRCT-DMWRYGQISA-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

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0116602)

Process

Naturally occurring process

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	8.8e-05 g/L	ALOGPS
logP	7.9	ALOGPS
logP	12.13	ChemAxon
logS	-7	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	41	ChemAxon
Refractivity	251.37 m³·mol⁻¹	ChemAxon
Polarizability	96.12 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

HMDB0116602

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

74878314

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131823246

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)) (CFc000097011)

MOL for CFc000097011 (PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)))

3D MOL for CFc000097011 (PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)))

3D SDF for CFc000097011 (PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)))

3D-SDF for CFc000097011 (PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)))

PDB for CFc000097011 (PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)))

3D PDB for CFc000097011 (PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)))

SMILES for CFc000097011 (PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)))

INCHI for CFc000097011 (PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)))

Structure for CFc000097011 (PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)))

3D Structure for CFc000097011 (PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)))