CHEBI:89372 - PC(20:0/18:3(6Z,9Z,12Z))

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ChEBI Name PC(20:0/18:3(6Z,9Z,12Z))
ChEBI ID CHEBI:89372
Stars This entity has been manually annotated by a third party.
Supplier Information No supplier information found for this compound.
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Lecithin ( LESS-ith-in; from the Ancient Greek λέκιθος lékithos "yolk") is a generic term to designate any group of yellow-brownish fatty substances occurring in animal and plant tissues which are amphiphilic – they attract both water and fatty substances (and so are both hydrophilic and lipophilic), and are used for smoothing food textures, emulsifying, homogenizing liquid mixtures, and repelling sticking materials. Lecithins are mixtures of glycerophospholipids including phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, and phosphatidic acid. Lecithin was first isolated in 1845 by the French chemist and pharmacist Théodore Gobley. In 1850, he named the phosphatidylcholine lécithine. Gobley originally isolated lecithin from egg yolk and established the complete chemical formula of phosphatidylcholine in 1874; in between, he demonstrated the presence of lecithin in a variety of biological materials, including venous blood, human lungs, bile, roe, and brains of humans, sheep and chicken. Lecithin can easily be extracted chemically using solvents such as hexane, ethanol, acetone, petroleum ether or benzene; or extraction can be done mechanically. Common sources include egg yolk, marine foods, soybeans, milk, rapeseed, cottonseed, and sunflower oil. It has low solubility in water, but is an excellent emulsifier. In aqueous solution, its phospholipids can form either liposomes, bilayer sheets, micelles, or lamellar structures, depending on hydration and temperature. This results in a type of surfactant that usually is classified as amphipathic. Lecithin is sold as a food additive and dietary supplement. In cooking, it is sometimes used as an emulsifier and to prevent sticking, for example in non-stick cooking spray.
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Formula C46H86NO8P
Net Charge 0
Average Mass 812.152
Monoisotopic Mass 811.60911
InChI InChI=1S/C46H86NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-26-28-30-32-34-36-38-45(48)52-42-44(43-54-56(50,51)53-41-40-47(3,4)5)55-46(49)39-37-35-33-31-29-27-24-21-19-17-15-13-11-9-7-2/h15,17,21,24,29,31,44H,6-14,16,18-20,22-23,25-28,30,32-43H2,1-5H3/b17-15-,24-21-,31-29-/t44-/m1/s1
InChIKey DLZPSAPMHALIOA-YNCVDBFYSA-N
SMILES C([C@@](COC(CCCCCCCCCCCCCCCCCCC)=O)(OC(CCCC/C=C\C/C=C\C/C=C\CCCCC)=O)[H])OP([O-])(=O)OCC[N+](C)(C)C
Metabolite of Species Details
Homo sapiens (NCBI:txid9606) Found in saliva (UBERON:0001836). See: Dame, ZT. et al. (2014) The Human Saliva Metabolome (manuscript in preparation)
Homo sapiens (NCBI:txid9606) Found in urine (BTO:0001419). See: PubMed
ChEBI Ontology
Outgoing PC(20:0/18:3(6Z,9Z,12Z)) (CHEBI:89372) is a 1,2-diacyl-sn-glycero-3-phosphocholine (CHEBI:57643)
Synonyms Sources
(2-{[(2R)-3-(icosanoyloxy)-2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium HMDB
1-Arachidonyl-2-g-linolenoyl-sn-glycero-3-phosphocholine HMDB
1-Arachidonyl-2-gamma-linolenoyl-sn-glycero-3-phosphocholine HMDB
GPCho(20:0/18:3) HMDB
GPCho(20:0/18:3n6) HMDB
GPCho(20:0/18:3w6) HMDB
GPCho(38:3) HMDB
Lecithin HMDB
PC aa C38:3 HMDB
PC(20:0/18:3) HMDB
PC(20:0/18:3n6) HMDB
PC(20:0/18:3w6) HMDB
PC(38:3) HMDB
Phosphatidylcholine(20:0/18:3) HMDB
Phosphatidylcholine(20:0/18:3n6) HMDB
Phosphatidylcholine(20:0/18:3w6) HMDB
Phosphatidylcholine(38:3) HMDB
Manual Xrefs Databases
HMDB0008271 HMDB
Lecithin Wikipedia
PHOSPHATIDYLCHOLINE MetaCyc
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