Glycerophospholipid biosynthetic pathway (Bos taurus)

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1, 93, 156, 197Shark liver oil1-Alkenyl-2-acylglycerophosphocholine(Plasmenylcholine)1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine(Plasmanylethanolamine)27, 43, 44, 63, 73...1-Alkyl-sn-glycerol 3-phosphate62, 96, 2981461-alkyl-2-acyl-sn-glycero-3-phosphocholine(Plasmanylcholine)167, 246, 2791-alkyl-2-acyl-sn-glycerol 3-phosphate(Plasmanic acid)1-alkenyl-2-acylglycerophosphoethanolamine(Plasmenylethanolamine)24, 67, 73, 77, 101...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.-35, 244LPIN2LPIN27, 11, 144, 191, 218...1-alkyl-2-acyl-sn-glycerophoethanolamine desaturase(Plasmanylethanolamine desaturase)EC 1.14.99.19CEPT167, 100Nitrogen group transferasaEC 2.6.-.-1-alkyl-2-acyl-sn-glycerol194NADPH + H+NADP(Coenzyme II)Acyl-CoACoA-SHPiCytidine diphosphate ethanolamine(CDP-ethanolamine)CMPO2 + NADH + H+2H2OCytochrome bCDP-cholineCMPCholineEthanolamine1-Alkyl-2-acetyl-sn-glycerol 3-phosphate213Alkylglycerophosphate 2-O-acetyltransferaseEC 2.3.1.105H2O40, 71, 109, 198PiAcetyl-CoACoA-SHAlkylacetylglycerophosphataseEC 3.1.3.591-Alkyl-2-acetyl-sn-glycerol10138, 175, 182, 213Diacylglycerol cholinephosphotransferase(Cholinephosphotransferase 1)EC 2.7.8.21-alkyl-2-acetyl-sn-glycero-3-phosphocholine(Platelet Activating Factor, PAF)104, 230, 26557, 97, 111, 125, 142...S-Adenosylmethionine(AdoMet)S-Adenosylhomocysteine(AdoHcy)N-MethyltransferaseEC 2.1.1.-Phospholipase CEC 3.1.4.3H2OEthanolamine phosphateCEPT179, 164, 183, 191, 238...CMPCDP-ethanolamineCDP-cholineCMP1-alkyl-sn-glycero-3-phosphocholine(Lyso PAF)PLA2G2A177, 22436, 47, 69, 85, 160...Acyl groupPLA2G2AAcetyl-CoA23, 114, 150, 212, 273...CoA-SH1-Alkyl-sn-glycerolAlkylglycerol kinaseEC 2.7.1.93194233ATPADPR-CH2-CH2-OH(Long chain fatty alcohol)CholineCDP-choline75, 81, 86, 88, 209...triacyl-sn-glycerol(Triacylglycerol; TAG)29, 41, 50, 187, 235...Adenosine triphosphate(ATP)sn-glycerol-3-phosphate(glycerol-3-P)51, 115, 181, 250, 2851,2-diacyl-sn-glycero-3-phosphate(Phosphatidic acid; PA)PPi49, 188, 274, 288NAD+(Coenzyme I)GPD1Pyrimidine Metabolism18, 78, 205, 232, 259Fatty acyl-CoADihydroxyacetone phosphate45, 1481,2-diacyl-sn-glycerol(1,2-diacylglycerol; 1,2-DAG)Glycerol2, 13, 92, 95NADH + H+Fatty acid MetabolismPhosphocholine(Choline-P)75, 1661,2-diacyl-sn-glycero-3-phosphocholine(PC, Lecithin)CoA-SH25, 75, 135, 143, 193...2-acyl-sn-glycero-3-phosphate(Lysophosphatidic acid; LPA)Glycolysis30, 76, 90, 91, 169...Adenosine diphosphate(ADP)CTPPiATPADPGKAcyl-CoA2-acylglycerol-3-phosphate O-acyltransferaseEC 2.3.1.52159Glycerol-3-phosphate 2-O-acyltransferaseEC 2.3.1.19834, 132, 202, 207, 210...Acyl coenzyme A(Acyl-CoA)Coenzyme A(CoA-SH)LPIN19, 16, 119, 271, 282...Acyl coenzyme A(Acyl-CoA)Coenzyme A(CoA-SH)CDS231, 147, 206, 228Cytidine triphosphate(CTP)PPiCHKB12, 81, 157, 163, 196...CHKBCHPT181, 82, 89, 257PEMT32, 58, 72, 79, 84...3 (S-adenosylhomocysteine)22, 110, 199, 215, 240...CMPAGPS66, 83, 105, 200, 204...1-Alkyldihydroxyacetone phosphate(Octanoyl DHAP)8, 80, 179, 2191-Acyl dihydroxyacetone phosphate(Acyl-DHAP)136, 247Coenzyme A(CoA-SH)R'-COOHGNPAT70, 106, 118, 152, 154...1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol)(PG)Cardiolipin(DPG, CL)19, 39, 121, 266Pi5, 15, 52, 59, 60, 102...InositolPhosphatidylinositol2,4,5-triphosphate[PIP3(3',4',5')]28, 38, 174, 223, 2431,2-diacyl-sn-glycero-3-phospho-(1'-myo-inositol)(PI)120, 239, 258, 280Cytidine monophosphate(CMP)1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycero-phosphate)(PGP)1,2-diacyl-sn-glycero-3-cytidine-5'-diphosphate(CDP-DAG, CMP-PA)139, 2341D-myo-Inositol-1-PPhosphatidylinositol-4,5-bisphosphate[PIP2(4',5')]D-Glucose-6-P33, 64, 68, 87, 141...Phosphatidylinositol-4-phosphate(PIP)20, 56, 64, 130, 275Glycerol-3-PCMPATPADPATPADPATPADPPGS1PTPMT126, 37, 108, 203, 26242, 221H2OCRLS1CDP-DAG55, 225CMPCDIPTPI4K2A54, 185, 201, 217, 231PIP5K1A56, 107, 113, 123, 128...3, 6, 264, 289Phosphatidylinositol-4,5-bisphosphate 3-kinaseEC 2.7.1.153Glycolysis1,2-diacyl-sn-glycero-3-phosphoserine(PS)17, 48, 74, 94, 98...Phosphorylethanolamine1,2-diacyl-sn-glycero-3-phosphoethanolamine(PE)2613 (S-adenosyl-methionine)99, 153, 155, 172, 180...EthanolamineSerineCytidine diphosphate ethanolamine(CDP-ethanolamine)CMP53, 129, 171, 245, 292ATPADPCTPPPiEthanolamineDiacylglycerol O-acyltransferaseEC 2.3.1.20CHKB14, 46, 61, 65, 127...PCYT221, 124, 149, 151CEPT1PTDSS14, 79, 126, 144, 161...74, 172GlycolysisBiosynthesis pathwaysDegradation pathwaysPathway origin


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.

Comments

HomologyConvert 
This pathway was inferred from Homo sapiens pathway WP2533(76320) with a 67.0% conversion rate.

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Bibliography

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History

View all...
CompareRevisionActionTimeUserComment
125339view04:23, 1 February 2023EgonwRemoved a duplicate reference
117524view11:09, 21 May 2021EweitzModified title
107065view14:15, 17 September 2019MaintBotChEBI identifier normalization
106448view11:33, 29 August 2019DeSlUpdated LipidMaps ID for TAG.
105941view11:47, 16 August 2019MaintBotHMDB identifier normalization
105334view12:06, 31 July 2019EgonwThe class, not the reference lipid.
93093view15:06, 28 July 2017DeSlOntology Term : 'glycerolipid metabolic pathway' added !
93081view10:55, 28 July 2017DeSlChanged choline pubchemsubstance database to pubchemcompound database to match ID.
93080view10:12, 28 July 2017DeSlChanged all the PubChem Substance ID's (around 13) to more stereospecific IDs.
93028view15:59, 26 July 2017DeSlAttempt 2: Changed hydrate ID from PubChem compounds to correct HMDB ID for D-glucose-6-P
93027view15:56, 26 July 2017DeSlChanged hydrate ID from PubChem compounds to correct HMDB ID for D-glucose-6-P
92862view15:21, 10 July 2017EgonwFixed PubChem compound ID (was salt, now pure compound).
88162view07:58, 29 July 2016Mkutmonfix unconnected lines
84332view09:08, 6 February 2016EgonwFixed PubChem identifers (removed CID/SID prefixes in the ID).
80785view15:26, 30 June 2015MkutmonNew pathway

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)MetaboliteHMDB0011750 (HMDB)
1-Alkenyl-2-acylglycerophosphocholine (Plasmenylcholine)MetaboliteCHEBI:17810 (ChEBI)
1-Alkyl-2-acetyl-sn-glycerol 3-phosphateMetaboliteCHEBI:17555 (ChEBI)
1-Alkyl-2-acetyl-sn-glycerolMetaboliteCHEBI:16291 (ChEBI)
1-Alkyl-sn-glycerol 3-phosphateMetaboliteCHEBI:17106 (ChEBI)
1-Alkyl-sn-glycerolMetaboliteCHEBI:15850 (ChEBI)
1-Alkyldihydroxyacetone phosphate (Octanoyl DHAP)Metabolite53481029 (PubChem-compound)
1-alkenyl-2-acylglycerophosphoethanolamine (Plasmenylethanolamine)MetaboliteCHEBI:17476 (ChEBI)
1-alkyl-2-acetyl-sn-glycero-3-phosphocholine (Platelet Activating Factor, PAF)MetaboliteCHEBI:36707 (ChEBI)
1-alkyl-2-acyl-sn-glycero-3-phosphocholine (Plasmanylcholine)MetaboliteCHEBI:36702 (ChEBI)
1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine (Plasmanylethanolamine)MetaboliteCHEBI:36712 (ChEBI)
1-alkyl-2-acyl-sn-glycerol 3-phosphate (Plasmanic acid)MetaboliteCHEBI:37296 (ChEBI)
1-alkyl-2-acyl-sn-glycerolMetabolite17756737 (PubChem-compound)
1-alkyl-2-acyl-sn-glycerophoethanolamine desaturase

(Plasmanylethanolamine desaturase)

EC 1.14.99.19		Protein
1-alkyl-sn-glycero-3-phosphocholine (Lyso PAF)MetaboliteCHEBI:36702 (ChEBI)
1D-myo-Inositol-1-PMetabolite5288642 (PubChem-compound)
2-acyl-sn-glycero-3-phosphate (Lysophosphatidic acid; LPA)MetaboliteLMGP10050000 (LIPID MAPS)
2-acylglycerol-3-phosphate O-acyltransferase EC 2.3.1.52Protein
2H2OMetabolite
3 (S-adenosyl-methionine)Metabolite34756 (PubChem-compound)
3 (S-adenosylhomocysteine)Metabolite439155 (PubChem-compound)
ADPMetabolite6022 (PubChem-compound)
AGPSProteinENSBTAG00000009897 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = S:O00116
ATPMetabolite5957 (PubChem-compound)
Acetyl-CoAMetabolite444493 (PubChem-compound)
Acyl coenzyme A (Acyl-CoA)MetaboliteCHEBI:17984 (ChEBI)
Acyl groupMetabolite
Acyl-CoA:1-alkyl-sn-glycero-3-phosphate 2-O-acyltransferase EC 2.3.1.-Protein
Acyl-CoAMetaboliteCHEBI:17984 (ChEBI)
Acylglycerone-phosphate reductase

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

EC 1.1.1.101		Protein
Adenosine diphosphate (ADP)Metabolite6022 (PubChem-compound)
Adenosine triphosphate (ATP)Metabolite5957 (PubChem-compound)
Alkylacetylglycerophosphatase EC 3.1.3.59Protein
Alkylglycerol kinase EC 2.7.1.93Protein
Alkylglycerophosphate 2-O-acetyltransferase EC 2.3.1.105Protein
CDIPTProteinENSBTAG00000007954 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = S:O14735
CDP-DAGMetaboliteLMGP13010000 (LIPID MAPS)
CDP-cholineMetabolite25202509 (PubChem-compound)
CDP-cholineMetaboliteCHEBI:49086 (ChEBI)
CDP-ethanolamineMetabolite123727 (PubChem-compound)
CDS2ProteinENSBTAG00000006066 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = S:O95674
CEPT1ProteinENSBTAG00000020169 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = S:Q9Y6K0
CHKBProteinENSBTAG00000016050 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = S:Q9Y259
CHPT1ProteinENSBTAG00000002490 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = S:Q8WUD6
CMPMetabolite6131 (PubChem-compound)
CRLS1ProteinENSBTAG00000000065 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = S:Q9UJA2
CTPMetabolite6176 (PubChem-compound)
Cardiolipin (DPG, CL)MetaboliteCHEBI:28494 (ChEBI)
CholineMetabolite305 (PubChem-compound)
CoA-SHMetabolite6816 (PubChem-compound)
Coenzyme A (CoA-SH)Metabolite6816 (PubChem-compound)
Cytidine diphosphate ethanolamine (CDP-ethanolamine)Metabolite123727 (PubChem-compound)
Cytidine monophosphate (CMP)Metabolite6131 (PubChem-compound)
Cytidine triphosphate (CTP)Metabolite6176 (PubChem-compound)
Cytochrome bMetaboliteCHEBI:38551 (ChEBI)
D-Glucose-6-PMetaboliteHMDB0003498 (HMDB)
Diacylglycerol O-acyltransferase EC 2.3.1.20ProteinENSBTAG00000047808 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = S:Q86VF5
Diacylglycerol cholinephosphotransferase

(Cholinephosphotransferase 1)

EC 2.7.8.2		Protein
Dihydroxyacetone phosphateMetabolite668 (PubChem-compound)
Ethanolamine phosphateMetabolite1015 (PubChem-compound)
EthanolamineMetabolite700 (PubChem-compound)
Fatty acid MetabolismPathway00071 (KEGG Pathway)
Fatty acyl-CoAMetaboliteLMFA07050000 (LIPID MAPS)
GKProteinENSBTAG00000008124 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = S:P32189
GNPATProteinENSBTAG00000010773 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = S:O15228
GPD1ProteinENSBTAG00000016296 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = S:P21695
Glycerol-3-PMetabolite7048686 (PubChem-compound)
Glycerol-3-phosphate 2-O-acyltransferase EC 2.3.1.198Protein
GlycerolMetabolite753 (PubChem-compound)
GlycolysisPathway00010 (KEGG Pathway)
H2O
InositolMetabolite892 (PubChem-compound)
LPIN1ProteinENSBTAG00000007689 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = S:Q14693
LPIN2ProteinENSBTAG00000012060 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = S:Q92539
N-Methyltransferase EC 2.1.1.-Protein
NAD+ (Coenzyme I)Metabolite5892 (PubChem-compound)
NADH + H+Metabolite439153 (PubChem-compound)
NADP (Coenzyme II)Metabolite5886 (PubChem-compound)
NADPH + H+Metabolite5884 (PubChem-compound)
Nitrogen group transferasa EC 2.6.-.-Protein
O2 + NADH + H+Metabolite
PCYT2ProteinENSBTAG00000001868 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = S:Q99447
PEMTProteinENSBTAG00000016432 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = S:Q9UBM1
PGS1ProteinENSBTAG00000000675 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = S:Q32NB8
PI4K2AProteinENSBTAG00000002010 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = S:Q9BTU6
PIP5K1AProteinENSBTAG00000006099 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = S:Q99755
PLA2G2AProteinENSBTAG00000005759 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = S:P14555
PPiMetabolite
PTDSS1ProteinENSBTAG00000013901 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = S:P48651
PTPMT1ProteinENSBTAG00000018479 (Ensembl) HomologyConvert: Homo sapiens to Bos taurus: Original ID = S:Q8WUK0
Phosphatidylinositol-4,5-bisphosphate [PIP2(4',5')]MetaboliteCHEBI:18348 (ChEBI)
Phosphatidylinositol-4,5-bisphosphate 3-kinase EC 2.7.1.153Protein
Phosphatidylinositol-4-phosphate (PIP)MetaboliteCHEBI:58178 (ChEBI)
Phosphatidylinositol2,4,5-triphosphate [PIP3(3',4',5')]MetaboliteLMGP09010001 (LIPID MAPS)
Phosphocholine (Choline-P)Metabolite1014 (PubChem-compound)
Phospholipase C EC 3.1.4.3Protein
PhosphorylethanolamineMetabolite1015 (PubChem-compound)
Pi
Pyrimidine MetabolismPathway00240 (KEGG Pathway)
S-Adenosylhomocysteine (AdoHcy)Metabolite439155 (PubChem-compound)
S-Adenosylmethionine (AdoMet)Metabolite34756 (PubChem-compound)
SerineMetabolite5951 (PubChem-compound)
Shark liver oil
sn-glycerol-3-phosphate (glycerol-3-P)Metabolite7048686 (PubChem-compound)
triacyl-sn-glycerol (Triacylglycerol; TAG)MetaboliteLMGL03010000 (LIPID MAPS)

Annotated Interactions

No annotated interactions
Retrieved from "https://classic.wikipathways.org/index.php/Pathway:WP3198"
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