Glycerophospholipid biosynthetic pathway (WP2533)

Homo sapiens

Glycerophospholipids or phosphoglycerides, in which the hydrophobic regions are composed of two fatty acids joined to glycerol; and sphingolipids, in which a single fatty acid is joined to a fatty amine, sphingosine, are glycerol-based phospholipids and the main component of biological membranes. The hydrophilic moieties in these amphipathic compounds may be as a simple as a single -OH at one end of the sterol ring system, or they may be more complex. Glycerophospholipds, as well as sphingolipids, contained polar or charged alcohols at their polar ends; some also contain phosphate groups. In glycerophospholipids, two fatty acids are ester-linked to glycerol at C-1 and C-2, and a highly polar or charged (and therefore hydrophilic) head group is attached to C-3 through a phosphodiester bond. All glycerophospholipds are derivatives of phosphatidic acid and are named for their polar head groups (e.g., phosphatidylethanolamine and phosphatidylcholine). All have a negative charge on the phosphate group at pH 7.0. The head-goup alcohol may also contribute one or more charges at pH near 7.0. The fatty acids in glycerophospholipds can be any of a wide variety. They are different in different species, in different tissues of the same species, and in different types of glycerophospholipids in the same cell or tissue. In general, glycerophospholipids contain a saturated fatty acid at C-1 and an unsaturated fatty acid at C-2, and, in general terms, the fatty acyl groups are generally 16 or 18 carbons long. Eukaryotic membranes contain significant amounts of two other types of glycerophospholipids: Plasmalogens and Alkylacylglycerophospholipids. Plasmalogens contain a hydrocarbon chain linked to glycerol C-1 via vinyl ether linkage whereas alkylacylglycerophospholipids the alkyl substituent at glycerol C-1 is attached via an ether linkage. About 20% of mammalian glycerophospholipids are plasmalogens, this percentage varies both from species to species and from tissue to tissue within a given organism. While plasmalogens comprise only about 0.8% of the phospholipids in human liver, they account for around 23% of those in human nervous tissue. The alkylacylglycerophospholipids are less abundant than the plasmalogens, e.g., about 59% of ethanolamine glycerophospholipids of human heart are plasmalogens, whereas only 3.6% are alkylacylglycerophospholipids. However, in bovine erythrocytes, 75% of the ethanolamine glycerophospholipids are of alkylacyl type.

Authors

Arturo Manzo-Fontes P D , Martina Summer-Kutmon , Egon Willighagen , Denise Slenter , Elisa Cirillo , Lauren J. Dupuis , Eric Weitz , Conroy lipids , and Kristina Hanspers

Activity

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Organisms

Homo sapiens

Communities

Annotations

Pathway Ontology

phosphatidylcholine metabolic pathway glycerophospholipid metabolic pathway phosphoinositide metabolic pathway

Participants

Label Type Compact URI Comment
Shark liver oil Metabolite wikidata:Q4380845
1-Alkenyl-2-acyl-glycerophosphocholine Metabolite chebi:17810 (Plasmenylcholine)
1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine Metabolite chebi:36712 (Plasmanylethanolamine)
1-Alkyl-sn-glycerol 3-phosphate Metabolite chebi:17106
1-alkyl-2-acyl-sn-glycero-3-phosphocholine(Plasmanylcholine) Metabolite chebi:36702
1-alkyl-2-acyl-sn-glycerol 3-phosphate(Plasmanic acid) Metabolite chebi:37296
1-alkenyl-2-acylglycero-phosphoethanolamine Metabolite chebi:17476 (Plasmenylethanolamine)
1-alkyl-2-acyl-sn-glycerol Metabolite pubchem.compound:17756737
NADPH + H+ Metabolite pubchem.compound:5884
NADP(Coenzyme II) Metabolite pubchem.compound:5886
Acyl-CoA Metabolite chebi:17984
CoA-SH Metabolite pubchem.compound:6816
Pi Metabolite pubchem.substance:1061
Cytidine diphosphate ethanolamine(CDP-ethanolamine) Metabolite pubchem.compound:123727
CMP Metabolite pubchem.compound:6131
2H2O Metabolite chebi:16240
CDP-choline Metabolite chebi:49086
Choline Metabolite pubchem.compound:305
Ethanolamine Metabolite pubchem.compound:700
1-Alkyl-2-acetyl-sn-glycerol 3-phosphate Metabolite chebi:17555
H2O Metabolite chebi:15377
Acetyl-CoA Metabolite pubchem.compound:444493
1-Alkyl-2-acetyl-sn-glycerol Metabolite chebi:16291
1-alkyl-2-acetyl-sn-glycero-3-phosphocholine(Platelet Activating Factor, PAF) Metabolite chebi:36707
S-Adenosylmethionine(AdoMet) Metabolite pubchem.compound:34756
S-Adenosylhomocysteine(AdoHcy) Metabolite pubchem.compound:439155
Ethanolamine phosphate Metabolite pubchem.compound:1015
CDP-ethanolamine Metabolite pubchem.compound:123727
1-alkyl-sn-glycero-3-phosphocholine(Lyso PAF) Metabolite chebi:36702
1-Alkyl-sn-glycerol Metabolite chebi:15850
ATP Metabolite pubchem.compound:5957
ADP Metabolite pubchem.compound:6022
triacyl-sn-glycerol(Triacylglycerol; TAG) Metabolite lipidmaps:LMGL03010000
Adenosine triphosphate(ATP) Metabolite pubchem.compound:5957
sn-glycerol-3-phosphate(glycerol-3-P) Metabolite pubchem.compound:7048686
1,2-diacyl-sn-glycero-3-phosphate(Phosphatidic acid; PA) Metabolite lipidmaps:LMGP10010000
PPi Metabolite chebi:45212
NAD+(Coenzyme I) Metabolite pubchem.compound:5892
Fatty acyl-CoA Metabolite lipidmaps:LMFA07050000
Dihydroxyacetone phosphate Metabolite pubchem.compound:668
1,2-diacyl-sn-glycerol(1,2-diacylglycerol; 1,2-DAG) Metabolite lipidmaps:LMGL02010000
Glycerol Metabolite pubchem.compound:753
NADH + H+ Metabolite pubchem.compound:439153
Phosphocholine(Choline-P) Metabolite pubchem.compound:1014
1,2-diacyl-sn-glycero-3-phosphocholine(PC, Lecithin) Metabolite lipidmaps:LMGP01010000
1-acyl-sn-glycero-3-phosphate(Lysophosphatidic acid; LPA) Metabolite lipidmaps:LMGP10050000
Adenosine diphosphate(ADP) Metabolite pubchem.compound:6022
CTP Metabolite pubchem.compound:6176
Acyl coenzyme A(Acyl-CoA) Metabolite chebi:17984
Coenzyme A(CoA-SH) Metabolite pubchem.compound:6816
Cytidine triphosphate(CTP) Metabolite pubchem.compound:6176
3 (S-adenosylhomocysteine) Metabolite pubchem.compound:439155
1-Alkyldihydroxyacetone phosphate(Octanoyl DHAP) Metabolite pubchem.compound:53481029
1-Acyl dihydroxyacetone phosphate(Acyl-DHAP) Metabolite hmdb:HMDB0011750
1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol)(PG) Metabolite lipidmaps:LMGP04010000
Cardiolipin(DPG, CL) Metabolite chebi:28494
Inositol Metabolite pubchem.compound:892
Phosphatidylinositol3,4,5-triphosphate[PIP3(3',4',5')] Metabolite lipidmaps:LMGP09010001
1,2-diacyl-sn-glycero-3-phospho-(1'-myo-inositol)(PI) Metabolite lipidmaps:LMGP06010000
Cytidine monophosphate(CMP) Metabolite pubchem.compound:6131
1,2-diacyl-sn-glycero-3-cytidine-5'-diphosphate(CDP-DAG, CMP-PA) Metabolite lipidmaps:LMGP13010000
1D-myo-Inositol-1-P Metabolite pubchem.compound:5288642
Phosphatidylinositol-4,5-bisphosphate[PIP2(4',5')] Metabolite chebi:18348
D-Glucose-6-P Metabolite hmdb:HMDB0003498
Phosphatidylinositol-4-phosphate(PIP) Metabolite chebi:58178
Glycerol-3-P Metabolite pubchem.compound:7048686
CDP-DAG Metabolite lipidmaps:LMGP13010000
1,2-diacyl-sn-glycero-3-phosphoserine(PS) Metabolite lipidmaps:LMGP03010000
Phosphorylethanolamine Metabolite pubchem.compound:1015
1,2-diacyl-sn-glycero-3-phosphoethanolamine(PE) Metabolite lipidmaps:LMGP02010000
3 (S-adenosyl-methionine) Metabolite pubchem.compound:34756
Serine Metabolite pubchem.compound:5951
GPAT1 Protein uniprot:Q9HCL2
IPMK Protein uniprot:Q8NFU5
Acylglycerone-phosphate reductaseEC 1.1.1.101 Protein uniprot:P40471 (1-alkyl-sn-glycerol-3-phosphate dehydrogenase)
Acyl-CoA:EC 2.3.1.- Protein eccode:2.3.1.- 1-alkyl-sn-glycero-3-phosphate 2-O-acyltransferase
1-alkyl-2-acyl-sn-glycero-3-phosphate phosphatase(Phosphatidate phosphatase)EC 3.1.3.4 Protein uniprot:Q92539
CDP-ethanolamine:(Ethanolaminephosphotransferase)EC 2.7.8.1 Protein uniprot:Q92539 1-alkyl-2-acyl-sn-glycerophosphoethanolamine transferase
(Plasmanylethanolamine desaturase)EC 1.14.99.19 Protein eccode:1.14.99.19 1-alkyl-2-acyl-sn-glycerophoethanolamine desaturase
CDP-choline:1-alkyl-2-acyl-sn-glycerophosphocholine transferase(Diacylglycerol cholinephosphotransferase)EC 2.7.8.2 Protein uniprot:Q9Y6K0
Nitrogen group transferasaEC 2.6.-.- Protein eccode:2.6.-.-
Cytochrome b Protein interpro:IPR005797
Alkylglycerophosphate 2-O-acetyltransferaseEC 2.3.1.105 Protein eccode:2.3.1.105
AlkylacetylglycerophosphataseEC 3.1.3.59 Protein eccode:3.1.3.59
Diacylglycerol cholinephosphotransferase(Cholinephosphotransferase 1)EC 2.7.8.2 Protein uniprot:P17898
N-MethyltransferaseEC 2.1.1.- Protein eccode:2.1.1.-
Phospholipase CEC 3.1.4.3 Protein eccode:3.1.4.3
Ethanolamine-phosphotransferaseEC 2.7.8.1 Protein uniprot:Q9Y6K0
Phospholipase A2EC 3.1.1.4 Protein uniprot:P14555
1-Alkylglycerophosphocholine O-acetyltransferaseEC 2.3.1.67 Protein uniprot:P14555
Alkylglycerol kinaseEC 2.7.1.93 Protein eccode:2.7.1.93
Glycerol-3-phosphate dehydrogenase (NAD+)EC 1.1.1.8 Protein uniprot:P21695
Glycerol kinaseEC 2.7.1.30 Protein uniprot:P32189
2-acylglycerol-3-phosphate O-acyltransferaseEC 2.3.1.52 Protein eccode:2.3.1.52
Glycerol-3-phosphate 1-O-acyltransferaseEC 2.3.1.15, mitochondrial Protein eccode:2.3.1.15
Phosphatidate phosphataseEC 3.1.3.4 Protein uniprot:Q14693
Phosphatidate cytidylyltransferaseEC 2.7.7.41 Protein uniprot:O95674
Choline kinaseEC 2.7.1.32 Protein uniprot:Q9Y259
Choline-phosphate cytidylyltransferaseEC 2.7.7.15 Protein uniprot:Q9Y259
Diacylglycerol cholinephosphotransferaseEC 2.7.8.2 Protein uniprot:Q8WUD6
Phosphatidylethanolamine N-methyltransferaseEC 2.1.1.17 Protein uniprot:Q9UBM1
Alkyldihydroxyacetonephosphate synthase(Alkyl-DHAP synthase)EC 2.5.1.26 Protein uniprot:O00116
Dihydroxyacetone phosphate acyltransferaseEC 2.3.1.42 Protein uniprot:O15228
CDP-diacylglycerol-glycerol-3-phosphate 3-phosphatidyltransferaseEC 2.7.8.5 Protein uniprot:Q32NB8
PhosphatidylglycerophosphataseEC 3.1.3.27 Protein uniprot:Q8WUK0
Cardiolipin synthaseEC 2.7.8.- Protein uniprot:Q9UJA2
CDP-diacylglyreol-inositol 3-phosphatidyltransferaseEC 2.7.8.11 Protein uniprot:O14735
1-phosphatidylinositol 4-kinaseEC 2.7.1.67 Protein uniprot:Q9BTU6
1-phosphatidylinositol 4-phosphate 5-kinaseEC 2.7.1.68 Protein uniprot:Q99755
Phosphatidylinositol-4,5-bisphosphate 3-kinaseEC 2.7.1.153 Protein eccode:2.7.1.153
Diacylglycerol O-acyltransferaseEC 2.3.1.20 Protein uniprot:Q86VF5
Ethanolamine kinaseEC 2.7.1.82 Protein uniprot:Q9Y259
Ethanolamine-phosphate cytidylyltransferaseEC 2.7.7.14 Protein uniprot:Q99447
EthanolaminephosphotransferaseEC 2.7.8.1 Protein uniprot:Q9Y6K0
L-serine-phosphatidylethanolamine phosphatidyltransferaseEC 2.7.8.29 Protein uniprot:P48651
GPAT2 Protein uniprot:Q6NUI2
GPAT3 Protein uniprot:Q53EU6
GPAT4 Protein uniprot:Q86UL3
Glycerol-3-phosphate 1-O-acyltransferaseEC 2.3.1.15 Protein eccode:2.3.1.15
PK3CG Protein uniprot:P48736
PK3CA Protein uniprot:P42336
PK3CB Protein uniprot:P42338
PK3CD Protein uniprot:O00329

References

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