Glycerophospholipid biosynthetic pathway (Homo sapiens)

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Biosynthesis pathways1,2-diacyl-sn-glycero-3-phosphoethanolamine(PE)NAD+(Coenzyme I)Fatty acid MetabolismPIP3[3',4',5']1,2-diacyl-sn-glycero-3-phosphate(Phosphatidic acid; PA)D-Glucose-6-P2-acyl-sn-glycero-3-phosphate(Lysophosphatidic acid; LPA)1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol)(PG)PIP2[4',5']3 (S-adenosyl-methionine)Inositoltriacyl-sn-glycerol(Triacylglycerol; TAG)Adenosine diphosphate(ADP)SerineCholinePi1,2-diacyl-sn-glycero-3-phospho-(1'-myo-inositol)(PI)Cytidine diphosphate choline(CDP-choline)PPi1,2-diacyl-sn-glycero-3-cytidine-5'-diphosphate(CDP-DAG, CMP-PA)Pyrimidine Metabolism1,2-diacyl-sn-glycero-3-phosphoserine(PS)Phosphatidylinositol-4-phosphate(PIP)1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycero-phosphate)(PGP)PhosphorylethanolamineDihydroxyacetone phosphate1,2-diacyl-sn-glycerol(1,2-diacylglycerol; 1,2-DAG)1,2-diacyl-sn-glycero-3-phosphocholine(PC, Lecithin)GlucosePhosphocholine(Choline-P)sn-glycerol-3-phosphate(glycerol-3-P)Cytidine diphosphate ethanolamine(CDP-ethanolamine)Cytidine monophosphate(CMP)GlycolysisGlycerolEthanolamineCoA-SH1D-myo-Inositol-1-PNADH + H+CTPGlycerol-3-phosphate dehydrogenase (NAD+)EC 1.1.1.8Cardiolipin(DPG, CL)Adenosine triphosphate(ATP)Glycerol-3-PPiCMPCMPATPADPCTPPPiEthanolamineATPADPATPADPATPADPATPADPGlycerol kinaseEC 2.7.1.30Acyl-CoA2-acylglycerol-3-phosphate O-acyltransferaseEC 2.3.1.52Glycerol-3-phosphate 2-O-acyltransferaseEC 2.3.1.198Acyl coenzyme A(Acyl-CoA)Coenzyme A(CoA-SH)Phosphatidate phosphataseEC 3.1.3.4Diacylglycerol O-acyltransferaseEC 2.3.1.20Acyl coenzyme A(Acyl-CoA)Coenzyme A(CoA-SH)Phosphatidate cytidylyltransferaseEC 2.7.7.41Cytidine triphosphate(CTP)PPiCDP-diacylglycerol-glycerol-3-phosphate 3-phosphatidyltransferaseEC 2.7.8.5PhosphatidylglycerophosphataseEC 3.1.3.27H2OCardiolipin synthaseEC 2.7.8.-CDP-DAGCMPCDP-diacylglyreol-inositol 3-phosphatidyltransferaseEC 2.7.8.111-phosphatidylinositol 4-kinaseEC 2.7.1.671-phosphatidylinositol 4-phosphate 5-kinaseEC 2.7.1.68Phosphatidylinositol-4,5-bisphosphate 3-kinaseEC 2.7.1.153Choline kinaseEC 2.7.1.32Choline-phosphate cytidylyltransferaseEC 2.7.7.15Diacylglycerol cholinephosphotransferaseEC 2.7.8.2Ethanolamine kinaseEC 2.7.1.82Ethanolamine-phosphate cytidylyltransferaseEC 2.7.7.14EthanolaminephosphotransferaseEC 2.7.8.1L-serine-phosphatidylethanolamine phosphatidyltransferaseEC 2.7.8.29Phosphatidylethanolamine N-methyltransferaseEC 2.1.1.173 (S-adenosylhomocysteine)CMPGlycolysisGlycolysisDegradation pathwaysPathway originAlkyldihydroxyacetonephosphate synthase(Alkyl-DHAP synthase)EC 2.5.1.261-Alkenyl-2-acylglycerophosphocholine(Plasmenylcholine)1-Alkyldihydroxyacetone phosphate(Octanoyl DHAP)1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine(Plasmanylethanolamine)1-Alkyl-sn-glycerol 3-phosphate1-alkyl-2-acyl-sn-glycero-3-phosphocholinePlsmanylcholine)1-Alkyl-2-acetyl-sn-glycero-3-phosphocholine(Platelet Activating Factor, PAF)1-alkyl-2-acyl-sn-glycerol 3-phosphate1-Acyl dihydroxyacetone phosphate(Acyl-DHAP)1-alkenyl-2-acylglycerophosphoethanolamine(Plasmenylethanolamine)Acylglycerone-phosphate reductase(1-alkyl-sn-glycerol-3-phosphate dehydrogenase)EC 1.1.1.101Acyl-CoA:1-alkyl-sn-glycero-3-phosphate 2-O-acyltransferaseEC 2.3.1.-1-alkyl-2-acyl-sn-glycero-3-phosphate phosphatase(Phosphatidate phosphatase)EC 3.1.3.4CDP-ethanolamine:1-alkyl-2-acyl-sn-glycerophosphoethanolamine transferase(Ethanolaminephosphotransferase)EC 2.7.8.11-alkyl-2-acyl-sn-glycerophoethanolamine desaturase(Plasmanylethanolamine desaturase)EC 1.14.99.19CDP-choline:1-alkyl-2-acyl-sn-glycerophosphocholine transferase(Diacylglycerol cholinephosphotransferase)EC 2.7.8.2CDP-choline:1-alkyl-2-acyl-sn-glycerophosphocholine transferase(Diacylglycerol cholinephosphotransferase)EC 2.7.8.2


Description

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.

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History

View all...
CompareRevisionActionTimeUserComment
126497view18:52, 10 May 2023KhanspersAdded lit ref and xref to Shark Liver Oil
124384view05:54, 24 October 2022EgonwTyped three metabolites
120261view13:40, 22 November 2021Conroy lipidsadded some DB crossrefs
117145view09:41, 18 May 2021EweitzModified title
113857view06:37, 2 December 2020EgonwReplaced a deleted PubMed identifier with the (working) duplicate
110695view13:58, 28 May 2020L DupuisUpdated Chebi identifiers
110693view13:50, 28 May 2020L DupuisCHeBi ID added for inorganic phosphate
107760view16:15, 1 November 2019DeSlOntology Term : 'phosphatidylcholine metabolic pathway' added !
107759view16:14, 1 November 2019DeSlOntology Term : 'phosphoinositide metabolic pathway' added !
107758view16:12, 1 November 2019DeSlOntology Term : 'PW:0001156' removed !
107757view16:11, 1 November 2019DeSlUpdated all curved lines for side metabolites to MIMconversion pointing to/away from anchor.
107756view15:48, 1 November 2019DeSlUpdated IDs for EC 2.7.1.153 (bottom right corner).
107755view09:55, 1 November 2019DeSlUpdated top half of PW, so side metabolites are connected to anchors.
107754view09:49, 1 November 2019DeSlAdded separate IDs for proteins under EC 2.3.1.15 .
107753view09:31, 1 November 2019DeSlChanged 2- to "1-" in 1-acyl-sn-glycero-3-phosphate (Lysophosphatidic acid; LPA) (reaction otherwise doesn't occure in humans.
107133view14:21, 17 September 2019MaintBotChEBI identifier normalization
106718view13:15, 17 September 2019MaintBotHMDB identifier normalization
106449view11:34, 29 August 2019DeSlUpdated LipidMaps ID for TAG.
105333view12:05, 31 July 2019EgonwThe class, not the reference lipid.
98235view12:32, 14 August 2018EgonwReplace a PubChem SID with a ChEBI ID.
98103view11:11, 20 July 2018DeSlOntology Term : 'glycerophospholipid metabolic pathway' added !
95594view14:18, 5 January 2018DeSlChanged part of the layout for readability of this pathway.
93096view15:17, 28 July 2017DeSlChanged all the PubChem Substance ID's (around 13) to more stereospecific IDs.
93077view08:52, 28 July 2017ElisaFixed unconnected lines and changed arrows in the legend from interactions to graphical elements
93029view16:02, 26 July 2017DeSlChanged hydrate ID from PubChem compounds to correct HMDB ID for D-glucose-6-P
92861view15:19, 10 July 2017EgonwFixed PubChem compound ID (was salt, now pure compound).
85647view17:10, 4 June 2016EgonwFixed the PubChem SID.
84117view10:00, 16 January 2016EgonwFixed a typo in the label.
83825view11:17, 14 December 2015EgonwRemoved data source info from identifiers.
76320view07:17, 2 July 2014Mkutmonadded chebi identifiers to metabolites annotated with GO terms
71989view11:13, 24 October 2013MkutmonChanged Unknown -> Metabolite for 3 (S-adenosyl-methionine) and 3 (S-adenosylhomocysteine)
71699view19:49, 17 October 2013MaintBotUpdated data sources
70448view22:31, 1 August 2013AmanzoPeriodical save, work in progress
70447view22:21, 1 August 2013AmanzoPeriodical save, work in progress
70404view16:13, 29 July 2013AmanzoWork in progress
70403view16:07, 29 July 2013AmanzoPeriodical save, work in progress
70390view16:04, 26 July 2013AmanzoPeriodical save, work in progress
70389view23:52, 25 July 2013AmanzoWork in progress
70388view23:42, 25 July 2013AmanzoPeriodical save, work in progress
70387view23:32, 25 July 2013AmanzoPeriodical save, work in progress
70384view17:34, 23 July 2013AmanzoWork in progress
70381view23:33, 21 July 2013AmanzoPeriodical save, work in progress
70380view23:22, 21 July 2013AmanzoPeriodical save, work in progress
70379view23:12, 21 July 2013AmanzoPeriodical save, work in progress
70378view23:02, 21 July 2013AmanzoPeriodical save, work in progress
70377view22:52, 21 July 2013AmanzoPeriodical save, work in progress
70376view22:42, 21 July 2013AmanzoPeriodical save, work in progress
70375view22:32, 21 July 2013AmanzoPeriodical save, work in progress
70374view22:21, 21 July 2013AmanzoPeriodical save, work in progress
70373view22:11, 21 July 2013AmanzoPeriodical save, work in progress

External references

DataNodes

View all...
NameTypeDatabase referenceComment
1,2-diacyl-sn-glycero-3-cytidine-5'-diphosphate (CDP-DAG, CMP-PA)MetaboliteLMGP13010000 (LIPID MAPS)
1,2-diacyl-sn-glycero-3-phosphate (Phosphatidic acid; PA)MetaboliteLMGP10010000 (LIPID MAPS)
1,2-diacyl-sn-glycero-3-phospho-(1'-myo-inositol) (PI)MetaboliteLMGP06010000 (LIPID MAPS)
1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycero-phosphate) (PGP)
1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol) (PG)MetaboliteLMGP04010000 (LIPID MAPS)
1,2-diacyl-sn-glycero-3-phosphocholine (PC, Lecithin)MetaboliteLMGP01010000 (LIPID MAPS)
1,2-diacyl-sn-glycero-3-phosphoethanolamine (PE)MetaboliteLMGP02010000 (LIPID MAPS)
1,2-diacyl-sn-glycero-3-phosphoserine (PS)MetaboliteLMGP03010000 (LIPID MAPS)
1,2-diacyl-sn-glycerol (1,2-diacylglycerol; 1,2-DAG)MetaboliteLMGL02010000 (LIPID MAPS)
1-Acyl dihydroxyacetone phosphate (Acyl-DHAP)MetaboliteHMDB11750 (HMDB)
1-Alkenyl-2-acylglycerophosphocholine (Plasmenylcholine)MetaboliteSID 4209 (PubChem-substance)
1-Alkyl-2-acetyl-sn-glycero-3-phosphocholine (Platelet Activating Factor, PAF)MetaboliteCHEBI:36707 (ChEBI)
1-Alkyl-sn-glycerol 3-phosphateMetaboliteSID 92741300 (PubChem-substance)
1-Alkyldihydroxyacetone phosphate (Octanoyl DHAP)MetaboliteCID 53481029 (PubChem-compound)
1-alkenyl-2-acylglycerophosphoethanolamine (Plasmenylethanolamine)MetaboliteSID 7325 (PubChem-substance)
1-alkyl-2-acyl-sn-glycero-3-phosphate phosphatase

(Phosphatidate phosphatase)

EC 3.1.3.4		ProteinQ92539 (Uniprot/TrEMBL)
1-alkyl-2-acyl-sn-glycero-3-phosphocholine Plsmanylcholine)MetaboliteCHEBI:36702 (ChEBI)
1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine (Plasmanylethanolamine)MetaboliteCHEBI:36712 (ChEBI)
1-alkyl-2-acyl-sn-glycerol 3-phosphateMetaboliteCHEBI:37296 (ChEBI)
1-alkyl-2-acyl-sn-glycerophoethanolamine desaturase

(Plasmanylethanolamine desaturase)

EC 1.14.99.19		ProteinEC 1.14.99.19 (Enzyme Nomenclature)
1-phosphatidylinositol 4-kinase EC 2.7.1.67ProteinQ9BTU6 (Uniprot/TrEMBL)
1-phosphatidylinositol 4-phosphate 5-kinase EC 2.7.1.68ProteinQ99755 (Uniprot/TrEMBL)
1D-myo-Inositol-1-PMetaboliteCID 5288642 (PubChem-compound)
2-acyl-sn-glycero-3-phosphate (Lysophosphatidic acid; LPA)MetaboliteLMGP10050000 (LIPID MAPS)
2-acylglycerol-3-phosphate O-acyltransferase EC 2.3.1.52ProteinEC 2.3.1.52 (Enzyme Nomenclature)
3 (S-adenosyl-methionine)CID 34756 (PubChem-compound)
3 (S-adenosylhomocysteine)CID 439155 (PubChem-compound)
ADPMetaboliteCID 6022 (PubChem-compound)
ATPMetaboliteCID 5957 (PubChem-compound)
Acyl coenzyme A (Acyl-CoA)MetaboliteSID 3342 (PubChem-substance)
Acyl-CoA:1-alkyl-sn-glycero-3-phosphate 2-O-acyltransferase EC 2.3.1.-ProteinEC 2.3.1.- (Enzyme Nomenclature)
Acyl-CoAMetaboliteSID 3342 (PubChem-substance)
Acylglycerone-phosphate reductase

(1-alkyl-sn-glycerol-3-phosphate dehydrogenase)

EC 1.1.1.101		ProteinP40471 (Uniprot/TrEMBL)
Adenosine diphosphate (ADP)MetaboliteCID 6022 (PubChem-compound)
Adenosine triphosphate (ATP)MetaboliteCID 5957 (PubChem-compound)
Alkyldihydroxyacetonephosphate synthase

(Alkyl-DHAP synthase)

EC 2.5.1.26		ProteinO00116 (Uniprot/TrEMBL)
CDP-DAGMetaboliteLMGP13010000 (LIPID MAPS)
CDP-choline:1-alkyl-2-acyl-sn-glycerophosphocholine transferase

(Diacylglycerol cholinephosphotransferase)

EC 2.7.8.2		ProteinQ9Y6K0 (Uniprot/TrEMBL)
CDP-diacylglycerol-glycerol-3-phosphate 3-phosphatidyltransferase EC 2.7.8.5ProteinQ32NB8 (Uniprot/TrEMBL)
CDP-diacylglyreol-inositol 3-phosphatidyltransferase EC 2.7.8.11ProteinO14735 (Uniprot/TrEMBL)
CDP-ethanolamine:1-alkyl-2-acyl-sn-glycerophosphoethanolamine transferase

(Ethanolaminephosphotransferase)

EC 2.7.8.1		ProteinQ92539 (Uniprot/TrEMBL)
CMPMetaboliteCID 6131 (PubChem-compound)
CTPMetaboliteCID 6176 (PubChem-compound)
Cardiolipin (DPG, CL)MetaboliteLMPG12010000 (LIPID MAPS)
Cardiolipin synthase EC 2.7.8.-ProteinQ9UJA2 (Uniprot/TrEMBL)
Choline kinase EC 2.7.1.32ProteinQ9Y259 (Uniprot/TrEMBL)
Choline-phosphate cytidylyltransferase EC 2.7.7.15ProteinQ9Y259 (Uniprot/TrEMBL)
CholineMetaboliteCID 305 (PubChem-substance)
CoA-SHMetaboliteCID 6816 (PubChem-compound)
Coenzyme A (CoA-SH)MetaboliteCID 6816 (PubChem-compound)
Cytidine diphosphate choline (CDP-choline)MetaboliteCID 25202509 (PubChem-compound)
Cytidine diphosphate ethanolamine (CDP-ethanolamine)MetaboliteCID 123727 (PubChem-compound)
Cytidine monophosphate (CMP)MetaboliteCID 6131 (PubChem-compound)
Cytidine triphosphate (CTP)MetaboliteCID 6176 (PubChem-compound)
D-Glucose-6-PMetaboliteCID 44134741 (PubChem-compound)
Diacylglycerol O-acyltransferase EC 2.3.1.20ProteinQ86VF5 (Uniprot/TrEMBL)
Diacylglycerol cholinephosphotransferase EC 2.7.8.2ProteinQ8WUD6 (Uniprot/TrEMBL)
Dihydroxyacetone phosphateMetaboliteCID 668 (PubChem-compound)
Ethanolamine kinase EC 2.7.1.82ProteinQ9Y259 (Uniprot/TrEMBL)
Ethanolamine-phosphate cytidylyltransferase EC 2.7.7.14ProteinQ99447 (Uniprot/TrEMBL)
EthanolamineMetaboliteCID 700 (PubChem-compound)
Ethanolaminephosphotransferase EC 2.7.8.1ProteinQ9Y6K0 (Uniprot/TrEMBL)
Fatty acid MetabolismPathway00071 (KEGG Pathway)
GlucoseMetabolite
Glycerol kinase EC 2.7.1.30ProteinP32189 (Uniprot/TrEMBL)
Glycerol-3-PMetaboliteCID 7048686 (PubChem-compound)
Glycerol-3-phosphate 2-O-acyltransferase EC 2.3.1.198ProteinO80437 (Uniprot/TrEMBL)
Glycerol-3-phosphate dehydrogenase (NAD+) EC 1.1.1.8ProteinP21695 (Uniprot/TrEMBL)
GlycerolMetaboliteCID 753 (PubChem-compound)
GlycolysisPathway00010 (KEGG Pathway)
H2O
InositolMetaboliteCID 892 (PubChem-compound)
L-serine-phosphatidylethanolamine phosphatidyltransferase EC 2.7.8.29ProteinP48651 (Uniprot/TrEMBL)
NAD+ (Coenzyme I)MetaboliteCID 5892 (PubChem-compound)
NADH + H+MetaboliteCID 439153 (PubChem-compound)
PIP2[4',5']MetaboliteLMGP08010003 (LIPID MAPS)
PIP3[3',4',5']MetaboliteLMGP09010001 (LIPID MAPS)
PPiMetabolite
Phosphatidate cytidylyltransferase EC 2.7.7.41ProteinO95674 (Uniprot/TrEMBL)
Phosphatidate phosphatase EC 3.1.3.4ProteinQ14693 (Uniprot/TrEMBL)
Phosphatidylethanolamine N-methyltransferase EC 2.1.1.17ProteinQ9UBM1 (Uniprot/TrEMBL)
Phosphatidylglycerophosphatase EC 3.1.3.27ProteinQ8WUK0 (Uniprot/TrEMBL)
Phosphatidylinositol-4,5-bisphosphate 3-kinase EC 2.7.1.153ProteinQ42338 (Uniprot/TrEMBL)
Phosphatidylinositol-4-phosphate (PIP)MetaboliteLMGP07010003 (LIPID MAPS)
Phosphocholine (Choline-P)MetaboliteCID 1014 (PubChem-compound)
PhosphorylethanolamineMetaboliteCID 1015 (PubChem-compound)
PiMetabolite
Pyrimidine MetabolismPathway00240 (KEGG Pathway)
SerineMetaboliteCID 5951 (PubChem-compound)
sn-glycerol-3-phosphate (glycerol-3-P)MetaboliteCID 7048686 (PubChem-compound)
triacyl-sn-glycerol (Triacylglycerol; TAG)MetaboliteLMGL03010000 (LIPID MAPS)

Annotated Interactions

No annotated interactions

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