Glycerophospholipid biosynthetic pathway (WP2533)

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.
last edited

Authors

Amanzo, MaintBot, Mkutmon, Egonw, DeSl, Elisa, L Dupuis, Eweitz, and Conroy lipids

Cited In

Organism

Homo sapiens

Communities

Annotations

Pathway Ontology: glycerophospholipid metabolic pathway phosphatidylcholine metabolic pathway phosphoinositide metabolic pathway

Participants

Label Type Compact Identifier
GPAT1 Protein uniprot:Q9HCL2
IPMK Protein uniprot:Q8NFU5
Shark liver oil Unknown None
1-Alkenyl-2-acyl-glycerophosphocholine Metabolite chebi:17810
1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine Metabolite chebi:36712
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
Acylglycerone-phosphate reductaseEC 1.1.1.101 Protein uniprot:P40471
Acyl-CoA:EC 2.3.1.- Protein eccode:2.3.1.-
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
(Plasmanylethanolamine desaturase)EC 1.14.99.19 Protein eccode:1.14.99.19
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.-.-
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
O2 + NADH + H+ Metabolite None
2H2O Metabolite chebi:16240
Cytochrome b Protein interpro:IPR005797
CDP-choline Metabolite chebi:49086
CMP Metabolite pubchem.compound:6131
Choline Metabolite pubchem.compound:305
Ethanolamine Metabolite pubchem.compound:700
1-Alkyl-2-acetyl-sn-glycerol 3-phosphate Metabolite chebi:17555
Alkylglycerophosphate 2-O-acetyltransferaseEC 2.3.1.105 Protein eccode:2.3.1.105
H2O Metabolite chebi:15377
Pi Metabolite pubchem.substance:1061
Acetyl-CoA Metabolite pubchem.compound:444493
CoA-SH Metabolite pubchem.compound:6816
AlkylacetylglycerophosphataseEC 3.1.3.59 Protein eccode:3.1.3.59
1-Alkyl-2-acetyl-sn-glycerol Metabolite chebi:16291
Diacylglycerol cholinephosphotransferase(Cholinephosphotransferase 1)EC 2.7.8.2 Protein uniprot:P17898
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
N-MethyltransferaseEC 2.1.1.- Protein eccode:2.1.1.-
Phospholipase CEC 3.1.4.3 Protein eccode:3.1.4.3
H2O Metabolite chebi:15377
Ethanolamine phosphate Metabolite pubchem.compound:1015
Ethanolamine-phosphotransferaseEC 2.7.8.1 Protein uniprot:Q9Y6K0
CMP Metabolite pubchem.compound:6131
CDP-ethanolamine Metabolite pubchem.compound:123727
CDP-choline Metabolite chebi:49086
CMP Metabolite pubchem.compound:6131
1-alkyl-sn-glycero-3-phosphocholine(Lyso PAF) Metabolite chebi:36702
Phospholipase A2EC 3.1.1.4 Protein uniprot:P14555
Acyl group Metabolite None
1-Alkylglycerophosphocholine O-acetyltransferaseEC 2.3.1.67 Protein uniprot:P14555
Acetyl-CoA Metabolite pubchem.compound:444493
CoA-SH Metabolite pubchem.compound:6816
1-Alkyl-sn-glycerol Metabolite chebi:15850
Alkylglycerol kinaseEC 2.7.1.93 Protein eccode:2.7.1.93
ATP Metabolite pubchem.compound:5957
ADP Metabolite pubchem.compound:6022
Choline Metabolite pubchem.compound:305
CDP-choline Metabolite chebi:49086
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
Glycerol-3-phosphate dehydrogenase (NAD+)EC 1.1.1.8 Protein uniprot:P21695
Pyrimidine Metabolism Pathway kegg.pathway:00240
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
Fatty acid Metabolism Pathway kegg.pathway:00071
Phosphocholine(Choline-P) Metabolite pubchem.compound:1014
1,2-diacyl-sn-glycero-3-phosphocholine(PC, Lecithin) Metabolite lipidmaps:LMGP01010000
CoA-SH Metabolite pubchem.compound:6816
1-acyl-sn-glycero-3-phosphate(Lysophosphatidic acid; LPA) Metabolite lipidmaps:LMGP10050000
Glycolysis Pathway kegg.pathway:00010
Adenosine diphosphate(ADP) Metabolite pubchem.compound:6022
CTP Metabolite pubchem.compound:6176
Pi Metabolite None
ATP Metabolite pubchem.compound:5957
ADP Metabolite pubchem.compound:6022
Glycerol kinaseEC 2.7.1.30 Protein uniprot:P32189
Acyl-CoA Metabolite chebi:17984
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
Acyl coenzyme A(Acyl-CoA) Metabolite chebi:17984
Coenzyme A(CoA-SH) Metabolite pubchem.compound:6816
Phosphatidate phosphataseEC 3.1.3.4 Protein uniprot:Q14693
Acyl coenzyme A(Acyl-CoA) Metabolite chebi:17984
Coenzyme A(CoA-SH) Metabolite pubchem.compound:6816
Phosphatidate cytidylyltransferaseEC 2.7.7.41 Protein uniprot:O95674
Cytidine triphosphate(CTP) Metabolite pubchem.compound:6176
PPi Metabolite None
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
3 (S-adenosylhomocysteine) Metabolite pubchem.compound:439155
CMP Metabolite pubchem.compound:6131
Alkyldihydroxyacetonephosphate synthase(Alkyl-DHAP synthase)EC 2.5.1.26 Protein uniprot:O00116
1-Alkyldihydroxyacetone phosphate(Octanoyl DHAP) Metabolite pubchem.compound:53481029
1-Acyl dihydroxyacetone phosphate(Acyl-DHAP) Metabolite hmdb:HMDB0011750
Coenzyme A(CoA-SH) Metabolite pubchem.compound:6816
Dihydroxyacetone phosphate acyltransferaseEC 2.3.1.42 Protein uniprot:O15228
1,2-diacyl-sn-glycero-3-phospho-(1-sn-glycerol)(PG) Metabolite LIPID MAPS
Cardiolipin(DPG, CL) Metabolite ChEBI
Pi Unknown PubChem-substance
Inositol Metabolite PubChem-compound
Phosphatidylinositol3,4,5-triphosphate[PIP3(3,4,5)] Metabolite lipidmaps:LMGP09010001
1,2-diacyl-sn-glycero-3-phospho-(1-myo-inositol)(PI) Metabolite LIPID MAPS
Cytidine monophosphate(CMP) Metabolite PubChem-compound
1,2-diacyl-sn-glycero-3-phospho-(1-sn-glycero-phosphate)(PGP) Unknown None
1,2-diacyl-sn-glycero-3-cytidine-5-diphosphate(CDP-DAG, CMP-PA) Metabolite LIPID MAPS
1D-myo-Inositol-1-P Metabolite PubChem-compound
Phosphatidylinositol-4,5-bisphosphate[PIP2(4,5)] Metabolite ChEBI
D-Glucose-6-P Metabolite HMDB
Phosphatidylinositol-4-phosphate(PIP) Metabolite ChEBI
Glycerol-3-P Metabolite PubChem-compound
CMP Metabolite PubChem-compound
ATP Metabolite PubChem-compound
ADP Metabolite PubChem-compound
ATP Metabolite PubChem-compound
ADP Metabolite PubChem-compound
ATP Metabolite PubChem-compound
ADP Metabolite PubChem-compound
CDP-diacylglycerol-glycerol-3-phosphate 3-phosphatidyltransferaseEC 2.7.8.5 Protein Uniprot-TrEMBL
PhosphatidylglycerophosphataseEC 3.1.3.27 Protein Uniprot-TrEMBL
H2O Unknown None
Cardiolipin synthaseEC 2.7.8.- Protein Uniprot-TrEMBL
CDP-DAG Metabolite LIPID MAPS
CMP Metabolite PubChem-compound
CDP-diacylglyreol-inositol 3-phosphatidyltransferaseEC 2.7.8.11 Protein Uniprot-TrEMBL
1-phosphatidylinositol 4-kinaseEC 2.7.1.67 Protein Uniprot-TrEMBL
1-phosphatidylinositol 4-phosphate 5-kinaseEC 2.7.1.68 Protein Uniprot-TrEMBL
Phosphatidylinositol-4,5-bisphosphate 3-kinaseEC 2.7.1.153 Protein Enzyme Nomenclature
Glycolysis Pathway KEGG Pathway
1,2-diacyl-sn-glycero-3-phosphoserine(PS) Metabolite LIPID MAPS
Phosphorylethanolamine Metabolite PubChem-compound
1,2-diacyl-sn-glycero-3-phosphoethanolamine(PE) Metabolite LIPID MAPS
3 (S-adenosyl-methionine) Metabolite PubChem-compound
Ethanolamine Metabolite PubChem-compound
Serine Metabolite PubChem-compound
Cytidine diphosphate ethanolamine(CDP-ethanolamine) Metabolite PubChem-compound
CMP Metabolite PubChem-compound
ATP Metabolite PubChem-compound
ADP Metabolite PubChem-compound
CTP Metabolite PubChem-compound
PPi Metabolite ChEBI
Ethanolamine Metabolite PubChem-compound
Diacylglycerol O-acyltransferaseEC 2.3.1.20 Protein Uniprot-TrEMBL
Ethanolamine kinaseEC 2.7.1.82 Protein Uniprot-TrEMBL
Ethanolamine-phosphate cytidylyltransferaseEC 2.7.7.14 Protein Uniprot-TrEMBL
EthanolaminephosphotransferaseEC 2.7.8.1 Protein Uniprot-TrEMBL
L-serine-phosphatidylethanolamine phosphatidyltransferaseEC 2.7.8.29 Protein Uniprot-TrEMBL
Glycolysis Pathway KEGG Pathway
GPAT2 Protein Uniprot-TrEMBL
GPAT3 Protein Uniprot-TrEMBL
GPAT4 Protein Uniprot-TrEMBL
Glycerol-3-phosphate 1-O-acyltransferaseEC 2.3.1.15 Protein Enzyme Nomenclature
PK3CG Protein Uniprot-TrEMBL
PK3CA Protein Uniprot-TrEMBL
PK3CB Protein Uniprot-TrEMBL
PK3CD Protein Uniprot-TrEMBL
None

References

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