Glycerophospholipid biosynthetic pathway (Homo sapiens)
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Description
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.Quality Tags
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History
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External references
DataNodes
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Name | Type | Database reference | Comment |
---|---|---|---|
(Plasmanylethanolamine desaturase) EC 1.14.99.19 | Protein | 1.14.99.19 (Enzyme Nomenclature) | 1-alkyl-2-acyl-sn-glycerophoethanolamine desaturase |
1,2-diacyl-sn-glycero-3-cytidine-5'-diphosphate (CDP-DAG, CMP-PA) | Metabolite | LMGP13010000 (LIPID MAPS) | |
1,2-diacyl-sn-glycero-3-phosphate (Phosphatidic acid; PA) | Metabolite | LMGP10010000 (LIPID MAPS) | |
1,2-diacyl-sn-glycero-3-phospho-(1'-myo-inositol) (PI) | Metabolite | LMGP06010000 (LIPID MAPS) | |
1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycero-phosphate) (PGP) | Metabolite | ||
1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol) (PG) | Metabolite | LMGP04010000 (LIPID MAPS) | |
1,2-diacyl-sn-glycero-3-phosphocholine (PC, Lecithin) | Metabolite | LMGP01010000 (LIPID MAPS) | |
1,2-diacyl-sn-glycero-3-phosphoethanolamine (PE) | Metabolite | LMGP02010000 (LIPID MAPS) | |
1,2-diacyl-sn-glycero-3-phosphoserine (PS) | Metabolite | LMGP03010000 (LIPID MAPS) | |
1,2-diacyl-sn-glycerol (1,2-diacylglycerol; 1,2-DAG) | Metabolite | LMGL02010000 (LIPID MAPS) | |
1-Acyl dihydroxyacetone phosphate (Acyl-DHAP) | Metabolite | HMDB0011750 (HMDB) | |
1-Alkenyl-2-acyl-
glycerophosphocholine | Metabolite | CHEBI:17810 (ChEBI) | (Plasmenylcholine) |
1-Alkyl-2-acetyl-sn-glycerol 3-phosphate | Metabolite | CHEBI:17555 (ChEBI) | |
1-Alkyl-2-acetyl-sn-glycerol | Metabolite | CHEBI:16291 (ChEBI) | |
1-Alkyl-sn-glycerol 3-phosphate | Metabolite | CHEBI:17106 (ChEBI) | |
1-Alkyl-sn-glycerol | Metabolite | CHEBI:15850 (ChEBI) | |
1-Alkyldihydroxyacetone phosphate (Octanoyl DHAP) | Metabolite | 53481029 (PubChem-compound) | |
1-Alkylglycerophosphocholine O-acetyltransferase EC 2.3.1.67 | Protein | P14555 (Uniprot-TrEMBL) | |
1-acyl-sn-glycero-3-phosphate (Lysophosphatidic acid; LPA) | Metabolite | LMGP10050000 (LIPID MAPS) | |
1-alkenyl-2-acylglycero-
phosphoethanolamine | Metabolite | CHEBI:17476 (ChEBI) | (Plasmenylethanolamine) |
1-alkyl-2-acetyl-sn-glycero-3-phosphocholine (Platelet Activating Factor, PAF) | Metabolite | CHEBI:36707 (ChEBI) | |
1-alkyl-2-acyl-sn-glycero-
3-phosphoethanolamine | Metabolite | CHEBI:36712 (ChEBI) | (Plasmanylethanolamine) |
1-alkyl-2-acyl-sn-glycero-3-phosphate phosphatase
(Phosphatidate phosphatase) EC 3.1.3.4 | Protein | Q92539 (Uniprot-TrEMBL) | |
1-alkyl-2-acyl-sn-glycero-3-phosphocholine (Plasmanylcholine) | Metabolite | CHEBI:36702 (ChEBI) | |
1-alkyl-2-acyl-sn-glycerol 3-phosphate (Plasmanic acid) | Metabolite | CHEBI:37296 (ChEBI) | |
1-alkyl-2-acyl-sn-glycerol | Metabolite | 17756737 (PubChem-compound) | |
1-alkyl-sn-glycero-3-phosphocholine (Lyso PAF) | Metabolite | CHEBI:36702 (ChEBI) | |
1-phosphatidylinositol 4-kinase EC 2.7.1.67 | Protein | Q9BTU6 (Uniprot-TrEMBL) | |
1-phosphatidylinositol 4-phosphate 5-kinase EC 2.7.1.68 | Protein | Q99755 (Uniprot-TrEMBL) | |
1D-myo-Inositol-1-P | Metabolite | 5288642 (PubChem-compound) | |
2-acylglycerol-3-phosphate O-acyltransferase EC 2.3.1.52 | Protein | 2.3.1.52 (Enzyme Nomenclature) | |
2H2O | Metabolite | 16240 (ChEBI) | |
3 (S-adenosyl-methionine) | Metabolite | 34756 (PubChem-compound) | |
3 (S-adenosylhomocysteine) | Metabolite | 439155 (PubChem-compound) | |
ADP | Metabolite | 6022 (PubChem-compound) | |
ATP | Metabolite | 5957 (PubChem-compound) | |
Acetyl-CoA | Metabolite | 444493 (PubChem-compound) | |
Acyl coenzyme A (Acyl-CoA) | Metabolite | CHEBI:17984 (ChEBI) | |
Acyl group | Metabolite | ||
Acyl-CoA: EC 2.3.1.- | Protein | 2.3.1.- (Enzyme Nomenclature) | 1-alkyl-sn-glycero-3-phosphate 2-O-acyltransferase |
Acyl-CoA | Metabolite | CHEBI:17984 (ChEBI) | |
Acylglycerone-phosphate reductase EC 1.1.1.101 | Protein | P40471 (Uniprot-TrEMBL) | (1-alkyl-sn-glycerol-3-phosphate dehydrogenase) |
Adenosine diphosphate (ADP) | Metabolite | 6022 (PubChem-compound) | |
Adenosine triphosphate (ATP) | Metabolite | 5957 (PubChem-compound) | |
Alkylacetylglycerophosphatase EC 3.1.3.59 | Protein | 3.1.3.59 (Enzyme Nomenclature) | |
Alkyldihydroxyacetonephosphate synthase
(Alkyl-DHAP synthase) EC 2.5.1.26 | Protein | O00116 (Uniprot-TrEMBL) | |
Alkylglycerol kinase EC 2.7.1.93 | Protein | 2.7.1.93 (Enzyme Nomenclature) | |
Alkylglycerophosphate 2-O-acetyltransferase EC 2.3.1.105 | Protein | 2.3.1.105 (Enzyme Nomenclature) | |
CDP-DAG | Metabolite | LMGP13010000 (LIPID MAPS) | |
CDP-choline:1-alkyl-2-acyl-sn-glycerophosphocholine transferase
(Diacylglycerol cholinephosphotransferase) EC 2.7.8.2 | Protein | Q9Y6K0 (Uniprot-TrEMBL) | |
CDP-choline | Metabolite | CHEBI:49086 (ChEBI) | |
CDP-diacylglycerol-glycerol-3-phosphate 3-phosphatidyltransferase EC 2.7.8.5 | Protein | Q32NB8 (Uniprot-TrEMBL) | |
CDP-diacylglyreol-inositol 3-phosphatidyltransferase EC 2.7.8.11 | Protein | O14735 (Uniprot-TrEMBL) | |
CDP-ethanolamine | Metabolite | 123727 (PubChem-compound) | |
CDP-ethanolamine:
(Ethanolaminephosphotransferase) EC 2.7.8.1 | Protein | Q92539 (Uniprot-TrEMBL) | 1-alkyl-2-acyl-sn-glycerophosphoethanolamine transferase |
CMP | Metabolite | 6131 (PubChem-compound) | |
CTP | Metabolite | 6176 (PubChem-compound) | |
Cardiolipin (DPG, CL) | Metabolite | CHEBI:28494 (ChEBI) | |
Cardiolipin synthase EC 2.7.8.- | Protein | Q9UJA2 (Uniprot-TrEMBL) | |
Choline kinase EC 2.7.1.32 | Protein | Q9Y259 (Uniprot-TrEMBL) | |
Choline-phosphate cytidylyltransferase EC 2.7.7.15 | Protein | Q9Y259 (Uniprot-TrEMBL) | |
Choline | Metabolite | 305 (PubChem-compound) | |
CoA-SH | Metabolite | 6816 (PubChem-compound) | |
Coenzyme A (CoA-SH) | Metabolite | 6816 (PubChem-compound) | |
Cytidine diphosphate ethanolamine (CDP-ethanolamine) | Metabolite | 123727 (PubChem-compound) | |
Cytidine monophosphate (CMP) | Metabolite | 6131 (PubChem-compound) | |
Cytidine triphosphate (CTP) | Metabolite | 6176 (PubChem-compound) | |
Cytochrome b | Protein | IPR005797 (InterPro) | |
D-Glucose-6-P | Metabolite | HMDB0003498 (HMDB) | |
Diacylglycerol O-acyltransferase EC 2.3.1.20 | Protein | Q86VF5 (Uniprot-TrEMBL) | |
Diacylglycerol cholinephosphotransferase
(Cholinephosphotransferase 1) EC 2.7.8.2 | Protein | P17898 (Uniprot-TrEMBL) | |
Diacylglycerol cholinephosphotransferase EC 2.7.8.2 | Protein | Q8WUD6 (Uniprot-TrEMBL) | |
Dihydroxyacetone phosphate acyltransferase EC 2.3.1.42 | Protein | O15228 (Uniprot-TrEMBL) | |
Dihydroxyacetone phosphate | Metabolite | 668 (PubChem-compound) | |
Ethanolamine kinase EC 2.7.1.82 | Protein | Q9Y259 (Uniprot-TrEMBL) | |
Ethanolamine phosphate | Metabolite | 1015 (PubChem-compound) | |
Ethanolamine-
phosphotransferase EC 2.7.8.1 | Protein | Q9Y6K0 (Uniprot-TrEMBL) | |
Ethanolamine-phosphate cytidylyltransferase EC 2.7.7.14 | Protein | Q99447 (Uniprot-TrEMBL) | |
Ethanolamine | Metabolite | 700 (PubChem-compound) | |
Ethanolaminephosphotransferase EC 2.7.8.1 | Protein | Q9Y6K0 (Uniprot-TrEMBL) | |
Fatty acid Metabolism | Pathway | 00071 (KEGG Pathway) | |
Fatty acyl-CoA | Metabolite | LMFA07050000 (LIPID MAPS) | |
GPAT1 | Protein | Q9HCL2 (Uniprot-TrEMBL) | |
GPAT2 | Protein | Q6NUI2 (Uniprot-TrEMBL) | |
GPAT3 | Protein | Q53EU6 (Uniprot-TrEMBL) | |
GPAT4 | Protein | Q86UL3 (Uniprot-TrEMBL) | |
Glycerol kinase EC 2.7.1.30 | Protein | P32189 (Uniprot-TrEMBL) | |
Glycerol-3-P | Metabolite | 7048686 (PubChem-compound) | |
Glycerol-3-phosphate 1-O-acyltransferase EC 2.3.1.15, mitochondrial | Protein | 2.3.1.15 (Enzyme Nomenclature) | |
Glycerol-3-phosphate 1-O-acyltransferase EC 2.3.1.15 | Protein | 2.3.1.15 (Enzyme Nomenclature) | |
Glycerol-3-phosphate dehydrogenase (NAD+) EC 1.1.1.8 | Protein | P21695 (Uniprot-TrEMBL) | |
Glycerol | Metabolite | 753 (PubChem-compound) | |
Glycolysis | Pathway | 00010 (KEGG Pathway) | |
H2O | Metabolite | ||
H2O | Metabolite | 15377 (ChEBI) | |
IPMK | Protein | Q8NFU5 (Uniprot-TrEMBL) | |
Inositol | Metabolite | 892 (PubChem-compound) | |
L-serine-phosphatidylethanolamine phosphatidyltransferase EC 2.7.8.29 | Protein | P48651 (Uniprot-TrEMBL) | |
N-Methyltransferase EC 2.1.1.- | Protein | 2.1.1.- (Enzyme Nomenclature) | |
NAD+ (Coenzyme I) | Metabolite | 5892 (PubChem-compound) | |
NADH + H+ | Metabolite | 439153 (PubChem-compound) | |
NADP (Coenzyme II) | Metabolite | 5886 (PubChem-compound) | |
NADPH + H+ | Metabolite | 5884 (PubChem-compound) | |
Nitrogen group transferasa EC 2.6.-.- | Protein | 2.6.-.- (Enzyme Nomenclature) | |
O2 + NADH + H+ | Metabolite | ||
PK3CA | Protein | P42336 (Uniprot-TrEMBL) | |
PK3CB | Protein | P42338 (Uniprot-TrEMBL) | |
PK3CD | Protein | O00329 (Uniprot-TrEMBL) | |
PK3CG | Protein | P48736 (Uniprot-TrEMBL) | |
PPi | Metabolite | ||
PPi | Metabolite | 45212 (ChEBI) | |
Phosphatidate cytidylyltransferase EC 2.7.7.41 | Protein | O95674 (Uniprot-TrEMBL) | |
Phosphatidate phosphatase EC 3.1.3.4 | Protein | Q14693 (Uniprot-TrEMBL) | |
Phosphatidylethanolamine N-methyltransferase EC 2.1.1.17 | Protein | Q9UBM1 (Uniprot-TrEMBL) | |
Phosphatidylglycerophosphatase EC 3.1.3.27 | Protein | Q8WUK0 (Uniprot-TrEMBL) | |
Phosphatidylinositol-4,5-bisphosphate [PIP2(4',5')] | Metabolite | CHEBI:18348 (ChEBI) | |
Phosphatidylinositol-4,5-bisphosphate 3-kinase EC 2.7.1.153 | Protein | 2.7.1.153 (Enzyme Nomenclature) | |
Phosphatidylinositol-4-phosphate (PIP) | Metabolite | CHEBI:58178 (ChEBI) | |
Phosphatidylinositol3,4,5-triphosphate [PIP3(3',4',5')] | Metabolite | LMGP09010001 (LIPID MAPS) | |
Phosphocholine (Choline-P) | Metabolite | 1014 (PubChem-compound) | |
Phospholipase A2 EC 3.1.1.4 | Protein | P14555 (Uniprot-TrEMBL) | |
Phospholipase C EC 3.1.4.3 | Protein | 3.1.4.3 (Enzyme Nomenclature) | |
Phosphorylethanolamine | Metabolite | 1015 (PubChem-compound) | |
Pi | Metabolite | ||
Pi | Metabolite | 1061 (PubChem-substance) | |
Pyrimidine Metabolism | Pathway | 00240 (KEGG Pathway) | |
S-Adenosylhomocysteine (AdoHcy) | Metabolite | 439155 (PubChem-compound) | |
S-Adenosylmethionine (AdoMet) | Metabolite | 34756 (PubChem-compound) | |
Serine | Metabolite | 5951 (PubChem-compound) | |
Shark liver oil | Metabolite | Q4380845 (Wikidata) | |
sn-glycerol-3-phosphate (glycerol-3-P) | Metabolite | 7048686 (PubChem-compound) | |
triacyl-sn-glycerol (Triacylglycerol; TAG) | Metabolite | LMGL03010000 (LIPID MAPS) |
Annotated Interactions
Source | Target | Type | Database reference | Comment |
---|---|---|---|---|
Phosphatidylinositol-4,5-bisphosphate [PIP2(4',5')] | Phosphatidylinositol3,4,5-triphosphate [PIP3(3',4',5')] | mim-conversion | 21293 (Rhea) | |
sn-glycerol-3-phosphate (glycerol-3-P) | 1-acyl-sn-glycero-3-phosphate (Lysophosphatidic acid; LPA) | mim-conversion | 15326 (Rhea) |