ChemFOnt: Showing chemical card for PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)) (CFc000097155)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:10:16 UTC

Chemfont ID

CFc000097155

Molecule Identification

Common Name

PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))

Definition

PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)) belongs to the class of glycerophosphoglycerophosphates, also called phosphatidylglycerophosphates (PGPs). These lipids contain a common glycerophosphate skeleton linked to at least one fatty acyl chain and a glycero-3-phosphate moiety. 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. PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one 4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl chain to the C-1 atom, and one 5Z,8Z,11Z,14Z-eicosatetraenoyl to the C-2 atom. In E. coli, PGPs can be found in the cytoplasmic membrane. The are synthesized by the addition of glycerol 3-phosphate to a CDP-diacylglycerol. In turn, PGPs are dephosphorylated to Phosphatidylglycerols (PGs) by the enzyme Phosphatidylglycerophosphatase.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Docosahexaenoyl-2-arachidonoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)	HMDB
PGP(22:6/20:4)	HMDB
PGP(22:6n3/20:4n6)	HMDB
PGP(22:6W3/20:4W6)	HMDB
PGP(42:10)	HMDB
3-sn-Phosphatidyl-1'-sn-glycerol 3'-phosphoric acid	HMDB
1-(4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)	HMDB
[(2S)-3-({[(2R)-3-[(7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-[(5Z,11Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonate	HMDB
1-docosahexaenoyl-2-arachidonoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)	SMPDB, HMDB
PGP(22:6/20:4)	SMPDB, HMDB
PGP(22:6n3/20:4n6)	SMPDB, HMDB
PGP(22:6w3/20:4w6)	SMPDB, HMDB
PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z))	SMPDB

Chemical Formula

C₄₈H₇₆O₁₃P₂

Average Molecular Weight

923.071

Monoisotopic Molecular Weight

922.476116503

IUPAC Name

[(2S)-3-({[(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid

Traditional Name

(2S)-3-{[(2R)-3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]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)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/C\C=C/CCCCC

InChI Identifier

InChI=1S/C48H76O13P2/c1-3-5-7-9-11-13-15-17-19-21-22-24-25-27-29-31-33-35-37-39-47(50)57-43-46(44-60-63(55,56)59-42-45(49)41-58-62(52,53)54)61-48(51)40-38-36-34-32-30-28-26-23-20-18-16-14-12-10-8-6-4-2/h5,7,11-14,17-20,22,24,26-29,32-35,45-46,49H,3-4,6,8-10,15-16,21,23,25,30-31,36-44H2,1-2H3,(H,55,56)(H2,52,53,54)/b7-5-,13-11-,14-12-,19-17-,20-18-,24-22-,28-26-,29-27-,34-32-,35-33-/t45-,46+/m0/s1

InChI Key

MWJPWYLOWRFABD-BNCNEJQVSA-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: HMDB0116746)

Process

Naturally occurring process

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.001 g/L	ALOGPS
logP	7.41	ALOGPS
logP	11.64	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	42	ChemAxon
Refractivity	263.36 m³·mol⁻¹	ChemAxon
Polarizability	99.45 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

HMDB0116746

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

74878426

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131823374

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)) (CFc000097155)

MOL for CFc000097155 (PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)))

3D MOL for CFc000097155 (PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)))

3D SDF for CFc000097155 (PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)))

3D-SDF for CFc000097155 (PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)))

PDB for CFc000097155 (PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)))

3D PDB for CFc000097155 (PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)))

SMILES for CFc000097155 (PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)))

INCHI for CFc000097155 (PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)))

Structure for CFc000097155 (PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)))

3D Structure for CFc000097155 (PGP(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:4(5Z,8Z,11Z,14Z)))