Classification Term: 168253

Diacylglycerophosphoglycerols [GP0401] (ontology term: 018b7781049cba9c325664f8d01e6e1b)

Diacylglycerophosphoglycerols [GP0401]

found 135 associated metabolites at sub_class metabolite taxonomy ontology rank level.

Ancestor: Glycerophosphoglycerols [GP04]

Child Taxonomies: There is no child term of current ontology term.

PG(16:0/18:1(9Z))

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

PG(16:0/18:1(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(16:0/18:1(9Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of oleic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, 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. PG(16:0/18:1(9Z)) is a phosphatidylglycerol. Phosphatidylglycerols consist of a glycerol 3-phosphate backbone esterified to either saturated or unsaturated fatty acids on carbons 1 and 2. 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. PG(16:0/18:1(9Z)), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one 9Z-octadecenoyl to the C-2 atom. In E. coli glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes.

PG 30:0

Hexadecanoic acid, 1-[[[(2,3-dihydroxypropoxy)hydroxyphosphinyl]oxy]methyl]-2-[(1-oxotetradecyl)oxy]ethyl ester, (R)-

C36H71O10P (694.4785)

Found in mouse lung; TwoDicalId=187; MgfFile=160901_Lung_EPA_Neg_07; MgfId=456

PG 36:2

9-Octadecenoic acid, 1-[[[(2,3-dihydroxypropoxy)hydroxyphosphinyl]oxy]methyl]-1,2-ethanediyl ester, [R-(E,E)]-

C42H79O10P (774.5411)

Found in mouse brain; TwoDicalId=225; MgfFile=160720_brain_AA_16_Neg; MgfId=745 Found in mouse spleen; TwoDicalId=162; MgfFile=160729_spleen_normal_02_Neg_never; MgfId=759 Found in mouse lung; TwoDicalId=97; MgfFile=160901_Lung_EPA_Neg_09; MgfId=645 Found in mouse heart; TwoDicalId=143; MgfFile=160902_Heart_Control_Neg_01_sute; MgfId=705 Found in mouse muscle; TwoDicalId=225; MgfFile=160824_Muscle_normal_Neg_01; MgfId=708 Found in mouse kidney; TwoDicalId=80; MgfFile=160827_Kidney_EPA_Neg_09; MgfId=986 Found in mouse spleen; TwoDicalId=76; MgfFile=160729_spleen_AA_17_Neg; MgfId=793

PG 36:3

1-(9Z-nonadecenoyl)-2-(9Z,12Z-heptadecadienoyl)-glycero-3-phospho-(1-sn-glycerol)

C42H77O10P (772.5254)

Found in mouse spleen; TwoDicalId=100; MgfFile=160729_spleen_normal_02_Neg; MgfId=545 Found in mouse kidney; TwoDicalId=640; MgfFile=160827_Kidney_EPA_Neg_09; MgfId=876

PG 36:4

1-hexadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phospho-(1-sn-glycerol)

C42H75O10P (770.5098)

Found in mouse small intestine; TwoDicalId=183; MgfFile=160907_Small_Intestine_EPA_Neg_08; MgfId=667 Found in mouse lung; TwoDicalId=255; MgfFile=160901_Lung_AA_Neg_17_never; MgfId=638 Found in mouse lung; TwoDicalId=15; MgfFile=160901_Lung_AA_Neg_17_never; MgfId=686

PG 36:5

1-(9Z,12Z,15Z-octadecatrienoyl)-2-(9Z,12Z-octadecadienoyl)-glycero-3-phospho-(1-sn-glycerol)

C42H73O10P (768.4941)

Found in mouse lung; TwoDicalId=93; MgfFile=160901_Lung_EPA_Neg_07; MgfId=445

PG 38:4

1-(11Z,14Z-eicosadienoyl)-2-(9Z,12Z-octadecadienoyl)-glycero-3-phospho-(1-sn-glycerol)

C44H79O10P (798.5411)

Found in mouse spleen; TwoDicalId=386; MgfFile=160729_spleen_normal_02_Neg_never; MgfId=724 Found in mouse lung; TwoDicalId=74; MgfFile=160901_Lung_AA_Neg_17; MgfId=746

PG 38:5

1-(11Z,14Z-eicosadienoyl)-2-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phospho-(1-sn-glycerol)

C44H77O10P (796.5254)

Found in mouse lung; TwoDicalId=317; MgfFile=160901_Lung_AA_Neg_17_never; MgfId=639 Found in mouse spleen; TwoDicalId=98; MgfFile=160729_spleen_AA_17_Neg_never; MgfId=705 Found in mouse lung; TwoDicalId=45; MgfFile=160901_Lung_EPA_Neg_09; MgfId=516

PG 40:5

1-(13Z,16Z-docosadienoyl)-2-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phospho-(1-sn-glycerol)

C46H81O10P (824.5567)

Found in mouse spleen; TwoDicalId=282; MgfFile=160729_spleen_AA_17_Neg; MgfId=694

PG 38:7

1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-2-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phospho-(1-sn-glycerol)

C44H73O10P (792.4941)

Found in mouse spleen; TwoDicalId=209; MgfFile=160729_spleen_EPA_09_Neg; MgfId=529

PG 42:9

1-(7Z,10Z,13Z,16Z-docosatetraenoyl)-2-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-glycero-3-phospho-(1-sn-glycerol)

C48H77O10P (844.5254)

Found in mouse spleen; TwoDicalId=206; MgfFile=160729_spleen_AA_18_Neg; MgfId=565 Found in mouse small intestine; TwoDicalId=478; MgfFile=160907_Small_Intestine_AA_Neg_18; MgfId=734 Found in mouse kidney; TwoDicalId=214; MgfFile=160827_Kidney_EPA_Neg_09; MgfId=764

PG 42:8

1-(7Z,10Z,13Z,16Z-docosatetraenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycero-3-phospho-(1-sn-glycerol)

C48H79O10P (846.5411)

Found in mouse spleen; TwoDicalId=111; MgfFile=160729_spleen_AA_17_Neg_never; MgfId=706

PG 42:10

1-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycero-3-phospho-(1-sn-glycerol)

C48H75O10P (842.5098)

Found in mouse small intestine; TwoDicalId=143; MgfFile=160907_Small_Intestine_AA_Neg_18; MgfId=680

PG 42:11

1-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycero-3-phospho-(1-sn-glycerol)

C48H73O10P (840.4941)

Found in mouse small intestine; TwoDicalId=258; MgfFile=160907_Small_Intestine_EPA_Neg_10; MgfId=621

PG 44:8

1-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-2-(13Z,16Z-docosadienoyl)-glycero-3-phospho-(1-sn-glycerol)

C50H83O10P (874.5724)

Found in mouse spleen; TwoDicalId=563; MgfFile=160729_spleen_AA_19_Neg; MgfId=730

PG 32:0

Octadecanoic acid, 3-[[(2,3-dihydroxypropoxy)hydroxyphosphinyl]oxy]-2-[(1-oxotetradecyl)oxy]propyl ester, (R)-

C38H75O10P (722.5098)

Found in mouse lung; TwoDicalId=20; MgfFile=160901_Lung_AA_Neg_17_never; MgfId=750

PG 32:1

1-pentadecanoyl-2-(9R, 11S-methylene-hexadecanoyl)-sn-glycero-3-phospho-(1-sn-glycerol)

C38H73O10P (720.4941)

Found in mouse muscle; TwoDicalId=543; MgfFile=160824_Muscle_normal_Neg_01_sute; MgfId=583 Found in mouse lung; TwoDicalId=35; MgfFile=160901_Lung_normal_Neg_03; MgfId=433

PG 34:0

1-pentadecanoyl-2-nonadecanoyl-glycero-3-phospho-(1-sn-glycerol)

C40H79O10P (750.5411)

Found in mouse kidney; TwoDicalId=795; MgfFile=160827_Kidney_EPA_Neg_10; MgfId=1103

PG 34:1

1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1-rac-glycerol)

C40H77O10P (748.5254)

A phosphatidylglycerol in which the 1- and 2-acyl groups are specified as palmitoyl and oleoyl respectively. Found in mouse lung; TwoDicalId=7; MgfFile=160901_Lung_normal_Neg_03; MgfId=540

PG 34:2

1-(9Z,12Z-heptadecadienoyl)-2-heptadecanoyl-glycero-3-phospho-(1-sn-glycerol)

C40H75O10P (746.5098)

Found in mouse spleen; TwoDicalId=624; MgfFile=160729_spleen_normal_02_Neg_never; MgfId=672 Found in mouse lung; TwoDicalId=3; MgfFile=160901_Lung_AA_Neg_17_never; MgfId=693

PG 38:6

1-(11Z,14Z-eicosadienoyl)-2-(6Z,9Z,12Z,15Z-octadecatetraenoyl)-glycero-3-phospho-(1-sn-glycerol)

C44H75O10P (794.5098)

Found in mouse spleen; TwoDicalId=67; MgfFile=160729_spleen_AA_16_Neg; MgfId=548 Found in mouse small intestine; TwoDicalId=196; MgfFile=160907_Small_Intestine_AA_Neg_16_never; MgfId=719 Found in mouse lung; TwoDicalId=19; MgfFile=160901_Lung_DHA_Neg_14; MgfId=516

PG 32:2

1-(9Z,12Z-heptadecadienoyl)-2-pentadecanoyl-glycero-3-phospho-(1-sn-glycerol)

C38H71O10P (718.4785)

Found in mouse lung; TwoDicalId=1940; MgfFile=160901_Lung_normal_Neg_02_never; MgfId=555

PG 34:3

1-(9Z,12Z-heptadecadienoyl)-2-(9Z-heptadecenoyl)-glycero-3-phospho-(1-sn-glycerol)

C40H73O10P (744.4941)

Found in mouse lung; TwoDicalId=482; MgfFile=160901_Lung_EPA_Neg_07; MgfId=428 Found in mouse spleen; TwoDicalId=1266; MgfFile=160729_spleen_normal_01_Neg; MgfId=498

PG 36:1

1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1-sn-glycerol)

C42H81O10P (776.5567)

Found in mouse kidney; TwoDicalId=383; MgfFile=160827_Kidney_EPA_Neg_06; MgfId=1084

PG 40:6

1-(7Z,10Z,13Z,16Z-docosatetraenoyl)-2-(9Z,12Z-octadecadienoyl)-glycero-3-phospho-(1-sn-glycerol)

C46H79O10P (822.5411)

Found in mouse spleen; TwoDicalId=165; MgfFile=160729_spleen_EPA_07_Neg_never; MgfId=707 Found in mouse lung; TwoDicalId=450; MgfFile=160901_Lung_EPA_Neg_09; MgfId=474 Found in mouse heart; TwoDicalId=173; MgfFile=160902_Heart_AA_Neg_20; MgfId=692

PG 40:7

1-(7Z,10Z,13Z,16Z-docosatetraenoyl)-2-(9Z,12Z,15Z-octadecatrienoyl)-glycero-3-phospho-(1-sn-glycerol)

C46H77O10P (820.5254)

Found in mouse spleen; TwoDicalId=130; MgfFile=160729_spleen_DHA_12_Neg; MgfId=609

PG 40:8

1-(7Z,10Z,13Z,16Z-docosatetraenoyl)-2-(6Z,9Z,12Z,15Z-octadecatetraenoyl)-glycero-3-phospho-(1-sn-glycerol)

C46H75O10P (818.5098)

Found in mouse spleen; TwoDicalId=53; MgfFile=160729_spleen_AA_17_Neg_never; MgfId=640 Found in mouse muscle; TwoDicalId=2321; MgfFile=160824_Muscle_AA_Neg_17; MgfId=540 Found in mouse small intestine; TwoDicalId=92; MgfFile=160907_Small_Intestine_EPA_Neg_08; MgfId=658

PG 44:10

1-(7Z,10Z,13Z,16Z-docosatetraenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-glycero-3-phospho-(1-sn-glycerol)

C50H79O10P (870.5411)

Found in mouse small intestine; TwoDicalId=650; MgfFile=160907_Small_Intestine_EPA_Neg_07; MgfId=807

PG 44:12

1,2-di-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phospho-(1-sn-glycerol)

C50H75O10P (866.5098)

Found in mouse small intestine; TwoDicalId=7; MgfFile=160907_Small_Intestine_DHA_Neg_15; MgfId=641