PC(18:1(9Z)/18:1(9Z)) (BioCAD00000019750)

blood feces saliva urine

Metabolite Card

Formula: C44H84NO8P (785.5934)
SMILES: CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC

Synonyms [en]

PC(18:1(9Z)/18:1(9Z)); 1,2-Dioleoyl-L-alpha-lecithin; 1,2-dioleoyl-sn-glycero-3-phosphocholine; PC(18:1/18:1); 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine; dioleoyl phosphatidylcholine

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

PC(18:1(9Z)/18:1(9Z)). 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000019750). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

PC(18:1(9Z)/18:1(9Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(18:1(9Z)/18:1(9Z)), in particular, consists of two chains of oleic acid at the C-1 and C-2 positions. The oleic acid moieties are derived from vegetable oils, especially olive and canola oil. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Dioleoylphosphatidylcholine is found in human platelets and red blood cells, in mitochondria from skeletal muscle, lung, umbilical artery and vein endothelial cells (PMID: 15351277, 7138900, 2351875, 4046747, 2755318).While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 10015-85-7
  • CAS Registry Number: 4235-95-4
  • CAS Registry Number: 52088-89-8
  • CAS Registry Number: 68737-67-7
  • PubChem: 10350317
  • PubChem: 5364680
  • PubChem: 6437081
  • ChEBI: ChEBI:74669
  • HMDB: HMDB0000593
  • HMDB: HMDB00593
  • HMDB: HMDB0062690
  • LipidMaps: LMGP01010890
  • BioCyc: CPD-2181
  • NCBI MeSH: 1,2-oleoylphosphatidylcholine
  • RefMet: RM0162116
  • MoNA: HMDB0000593_ms_ms_819
  • MoNA: HMDB0000593_ms_ms_820
  • MoNA: HMDB0000593_ms_ms_821
  • Metlin: METLIN_5572

Class / Ontology

Metabolic Network
ID EC Number Name
Rhea:RHEA:37388 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA => 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA
Rhea:RHEA:37389 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA => 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA
Rhea:RHEA:37390 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + (9Z)-octadecenoyl-CoA <=> 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + CoA
Rhea:RHEA:38700 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + H2O => (9Z-octadecenoyl)-sn-glycero-3-phosphocholine + (9Z)-octadecenoate + H+
Rhea:RHEA:38701 (9Z-octadecenoyl)-sn-glycero-3-phosphocholine + (9Z)-octadecenoate + H+ => 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + H2O
Rhea:RHEA:38702 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + H2O <=> (9Z-octadecenoyl)-sn-glycero-3-phosphocholine + (9Z)-octadecenoate + H+
Rhea:RHEA:38704 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine => 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
Rhea:RHEA:38705 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine => 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine
Rhea:RHEA:38706 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine + N-(acetyl)-sphing-4-enine <=> 1-(9Z-octadecenoyl)-N-(acetyl)-sphing-4-enine + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
Rhea:RHEA:38708 1-O-hexadecyl-2-acetyl-sn-glycerol + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine => 1-O-hexadecyl-2-acetyl-3-(9Z)-octadecenoyl-sn-glycerol + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine
Rhea:RHEA:38709 1-O-hexadecyl-2-acetyl-3-(9Z)-octadecenoyl-sn-glycerol + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine => 1-O-hexadecyl-2-acetyl-sn-glycerol + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
Rhea:RHEA:38710 1-O-hexadecyl-2-acetyl-sn-glycerol + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine <=> 1-O-hexadecyl-2-acetyl-3-(9Z)-octadecenoyl-sn-glycerol + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine
Rhea:RHEA:38712 1-O-hexadecylglycerol + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine => 1-O-hexadecyl-3-(9Z)-octadecenoylglycerol + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine
Rhea:RHEA:38713 1-O-hexadecyl-3-(9Z)-octadecenoylglycerol + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine => 1-O-hexadecylglycerol + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
Rhea:RHEA:38714 1-O-hexadecylglycerol + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine <=> 1-O-hexadecyl-3-(9Z)-octadecenoylglycerol + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine
Rhea:RHEA:38724 1-O-hexadecyl-2-O-methyl-sn-glycerol + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine => 1-O-hexadecyl-2-O-methyl-3-(9Z)-octadecenoyl-sn-glycerol + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine
Rhea:RHEA:38725 1-O-hexadecyl-2-O-methyl-3-(9Z)-octadecenoyl-sn-glycerol + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine => 1-O-hexadecyl-2-O-methyl-sn-glycerol + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
Rhea:RHEA:38726 1-O-hexadecyl-2-O-methyl-sn-glycerol + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine <=> 1-O-hexadecyl-2-O-methyl-3-(9Z)-octadecenoyl-sn-glycerol + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine
Rhea:RHEA:38728 1-hexadecanoyl-sn-glycerol + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine => 1-hexadecanoyl-3-(9Z)-octadecenoyl-sn-glycerol + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine
Rhea:RHEA:38729 1-hexadecanoyl-3-(9Z)-octadecenoyl-sn-glycerol + (9Z-octadecenoyl)-sn-glycero-3-phosphocholine => 1-hexadecanoyl-sn-glycerol + 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
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Organism Source

Taxonomy Source

Pathway Synthetic

pathway id name
BioCyc:ARA_PWY-762 phospholipid desaturation
BioCyc:META_PWY-762 phospholipid desaturation
PlantCyc:REDCLOVER_PWY-762 phospholipid desaturation
PlantCyc:SELAGINELLA_PWY-762 phospholipid desaturation
PlantCyc:SFALLAX_PWY-762 phospholipid desaturation
PlantCyc:SORGHUMBICOLOR_PWY-762 phospholipid desaturation
PlantCyc:SPIRODELA_PWY-762 phospholipid desaturation
PlantCyc:SUNFLOWER_PWY-762 phospholipid desaturation
PlantCyc:MGUTTATUS_PWY-762 phospholipid desaturation
PlantCyc:MSINENSIS_PWY-762 phospholipid desaturation
PlantCyc:NTABACUM_TN90_PWY-762 phospholipid desaturation
PlantCyc:OEUROPAEA_SYLVESTRIS_PWY-762 phospholipid desaturation
PlantCyc:OILPALM_PWY-762 phospholipid desaturation
PlantCyc:ONIVARA_PWY-762 phospholipid desaturation
PlantCyc:ORYZA_PWY-762 phospholipid desaturation
PlantCyc:PAXILLARIS_PWY-762 phospholipid desaturation
PlantCyc:PINEAPPLE_PWY-762 phospholipid desaturation
PlantCyc:CRUBELLA_PWY-762 phospholipid desaturation
PlantCyc:CUCUMBER_PWY-762 phospholipid desaturation
PlantCyc:DROTUNDATA_PWY-762 phospholipid desaturation
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