Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:41:55 UTC
Update Date2024-04-30 20:03:55 UTC
Metabolite IDMMDBc0033273
Metabolite Identification
Common NamePC(16:0/16:1(9Z))
DescriptionPC(16:0/16:1(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(16:0/16:1(9Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of palmitoleic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the palmitoleic acid moiety is derived from animal fats and vegetable oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.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.
Structure
Synonyms
ValueSource
(2R)-2-[(9Z)-Hexadec-9-enoyloxy]-3-(palmitoyloxy)propyl 2-(trimethylammonio)ethyl phosphateChEBI
(2R)-3-(Hexadecanoyloxy)-2-[(9Z)-hexadec-9-enoyloxy]propyl 2-(trimethylammonio)ethyl phosphateChEBI
(R-(Z))-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-((1-oxo-9-hexadecenyl)oxy)-3,5,9-trioxa-4-phosphapentacosan-1-aminium, hydroxide, inner salt, 4-oxideChEBI
1-C16:0-2-C16:1(Omega-7)-phosphatidylcholineChEBI
1-Hexadecanoyl-2-(9Z)-hexadecenoyl-sn-glycero-3-phosphocholineChEBI
1-Hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholineChEBI
1-Hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholine zwitterionChEBI
1-Palmitoyl-2-palmitoleoyl-GPCChEBI
1-Palmitoyl-2-palmitoleoyl-GPC (16:0/16:1)ChEBI
GPC(16:0/16:1)ChEBI
PC(16:0/16:1)ChEBI
PC(16:0/16:1omega7)ChEBI
PC(32:1)ChEBI
Phosphatidylcholine(16:0/16:1)ChEBI
Phosphatidylcholine(16:0/16:1omega7)ChEBI
Phosphatidylcholine(32:1)ChEBI
sn-1-Palmitoyl-2-palmitoleoylphosphatidylcholineChEBI
(2R)-2-[(9Z)-Hexadec-9-enoyloxy]-3-(palmitoyloxy)propyl 2-(trimethylammonio)ethyl phosphoric acidGenerator
(2R)-3-(Hexadecanoyloxy)-2-[(9Z)-hexadec-9-enoyloxy]propyl 2-(trimethylammonio)ethyl phosphoric acidGenerator
PalmitoylpalmitoleoylphosphatidylcholineHMDB
1-(16,16,16-Trideuteriopalmitoyl)-2-palmitoleoyl-sn-glycero-3-phosphocholineHMDB
1-Palmitoyl-2-palmitoleoyl-sn-glycero-3-phosphocholine, (Z)-isomerHMDB
(CD3-16.0)(16.1)PCHMDB
1-Palmitoyl-2-palmitoleoyl-sn-glycero-3-phosphocholineHMDB
PPA-GPCHMDB
GPCho(16:0/16:1)HMDB
LecithinHMDB
GPCho(32:1)HMDB
1-Palmitoyl-2-palmitoleoyl-sn-glycero-phosphatidylcholineHMDB
1-Palmitoyl-2-palmitoleoylphosphatidylcholineHMDB
GPC(16:0/16:1(9Z))HMDB
GPC(16:0/16:1n7)HMDB
GPC(16:0/16:1W7)HMDB
GPC(32:1)HMDB
GPCho(16:0/16:1(9Z))HMDB
GPCho(16:0/16:1n7)HMDB
GPCho(16:0/16:1W7)HMDB
L-alpha-1-Palmitoyl-2-palmitoleoylphosphatidylcholineHMDB
L-Α-1-palmitoyl-2-palmitoleoylphosphatidylcholineHMDB
PC(16:0/16:1n7)HMDB
PC(16:0/16:1W7)HMDB
Phosphatidylcholine(16:0/16:1(9Z))HMDB
Phosphatidylcholine(16:0/16:1n7)HMDB
Phosphatidylcholine(16:0/16:1W7)HMDB
PC(16:0/16:1(9Z))Lipid Annotator
Molecular FormulaC40H78NO8P
Average Mass732.023
Monoisotopic Mass731.546504989
IUPAC Name(2-{[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(hexadecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry Number8002-43-5
SMILES
CCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCC
InChI Identifier
InChI=1S/C40H78NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h17,19,38H,6-16,18,20-37H2,1-5H3/b19-17-/t38-/m1/s1
InChI KeyQIBZFHLFHCIUOT-NPBIGWJUSA-N