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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-07-07 20:53:58 UTC
HMDB IDHMDB0000564
Secondary Accession Numbers
  • HMDB0000804
  • HMDB0005250
  • HMDB0007968
  • HMDB00564
  • HMDB00804
  • HMDB05250
  • HMDB07968
Metabolite Identification
Common NamePC(32:0)
DescriptionPC(16:0/16:0) 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(16:0/16:0), in particular, consists of two chains of palmitic acid at the C-1 and C-2 positions. The palmitic acid moieties are derived from fish oils, milk fats, vegetable oils and animal fats. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Dipalmitoylphosphatidylcholine (DPPC) is the major constituent of pulmonary surfactant. It is also used for research purposes in studying liposomes, lipid bilayers, and model biological membranes. 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
Data?1657835202
Synonyms
ValueSource
1,2-Bis(hexadecanoyl)-sn-glycero-3-phosphocholineChEBI
1,2-Dipalmitoyl-L-lecithinChEBI
1,2-Dipalmitoyl-sn-glycero-3-phosphatidylcholineChEBI
1,2-Dipalmitoyl-sn-glycero-3-phosphocholineChEBI
1,2-DipalmitoylphosphatidylcholineChEBI
1-16:0-2-16:0-PhosphatidylcholineChEBI
16:0-16:0-PCChEBI
Colfosceril palmitateChEBI
Colfoscerili palmitasChEBI
Dipalmitoyl phosphatidylcholineChEBI
Dipalmitoyl-GPCChEBI
DipalmitoylphosphatidylcholineChEBI
GPC(16:0/16:0)ChEBI
GPCho 16:0/16:0ChEBI
GPCho(16:0/16:0)ChEBI
Palmitate de colfoscerilChEBI
Palmitato de colfosceriloChEBI
PC 16:0/16:0ChEBI
PC(32:0)ChEBI
Phosphatidylcholine 16:0/16:0ChEBI
Phosphatidylcholine(16:0/16:0)ChEBI
Phosphatidylcholine(32:0)ChEBI
Colfosceril palmitic acidGenerator
Palmitic acid de colfoscerilGenerator
1,2-Dipalmitoyl-rac-glycero-3-phosphocholineHMDB
LecithinHMDB
1,2-Dihexadecanoyl-rac-glycero-3-phosphocholineHMDB
GPCho(32:0)HMDB
(R)-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacosan-1-aminium 4-oxide hydroxide inner saltHMDB
(R)-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacosan-1-aminium 4-oxide inner saltHMDB
1,2-Bis(palmitoyl)-sn-glycero-3-phosphocholineHMDB
1,2-Dihexadecanoyl-sn-glycerol-3-phosphorylcholineHMDB
1,2-Dipalmitoyl-3-sn-phosphatidylcholineHMDB
1,2-Dipalmitoyl-L-3-phosphatidylcholineHMDB
1,2-Dipalmitoyl-L-a-lecithinHMDB
1,2-Dipalmitoyl-L-a-phosphatidylcholineHMDB
1,2-Dipalmitoyl-L-alpha-lecithinHMDB
1,2-Dipalmitoyl-L-alpha-phosphatidylcholineHMDB
1,2-Dipalmitoyl-L-phosphatidylcholineHMDB
1,2-Dipalmitoyl-sn-3-glycerophosphocholineHMDB
1,2-Dipalmitoyl-sn-glycero-3-phosphorylcholineHMDB
1,2-Dipalmitoyl-sn-glycerol-3-phosphocholineHMDB
1,2-Dipalmitoyl-sn-glycerophosphocholineHMDB
1,2-Dipalmitoyl-sn-glycerophosphorylcholineHMDB
1,2-Dipalmitoyl-sn-glyceryl-3-phosphocholineHMDB
1,2-Dipalmitoyl-sn-phosphatidylcholineHMDB
1,2-Dipalmitoylglycero-3-phosphocholineHMDB
1,2-L-a-DipalmitoylphosphatidylcholineHMDB
1,2-L-alpha-DipalmitoylphosphatidylcholineHMDB
b,g-Dipalmitoyl L-a-phosphatidylcholineHMDB
b,g-Dipalmitoyl L-alpha-phosphatidylcholineHMDB
b,g-Dipalmitoyl-L-(a)-lecithinHMDB
b,g-Dipalmitoyl-L-phosphatidylcholineHMDB
Dihexadecanoyl-sn-glycero-3-phosphocholineHMDB
Dipalmitoyl L-a-phosphatidylcholineHMDB
Dipalmitoyl L-alpha-phosphatidylcholineHMDB
Dipalmitoyl-L-3-glycerylphosphorylcholineHMDB
Dipalmitoyl-L-a-lecithinHMDB
Dipalmitoyl-L-a-phosphatidylcholineHMDB
Dipalmitoyl-L-alpha-lecithinHMDB
Dipalmitoyl-L-alpha-phosphatidylcholineHMDB
Dipalmitoyl-sn-3-phosphatidylcholineHMDB
DPPCHMDB
L-1,2-Dipalmitoyl-a-lecithinHMDB
L-1,2-Dipalmitoyl-alpha-lecithinHMDB
L-1,2-DipalmitoylphosphatidylcholineHMDB
L-a-1,2-Dipalmitoyl lecithinHMDB
L-a-DipalmitoylecithinHMDB
L-a-DipalmitoyllecithinHMDB
L-a-DipalmitoylphosphatidylcholineHMDB
L-a-DPPCHMDB
L-alpha-1,2-Dipalmitoyl lecithinHMDB
L-alpha-DipalmitoylecithinHMDB
L-alpha-DipalmitoyllecithinHMDB
L-alpha-DipalmitoylphosphatidylcholineHMDB
L-alpha-DPPCHMDB
L-b,g-Dipalmitoyl-a-lecithinHMDB
L-b,g-Dipalmitoyl-a-phosphatidylcholineHMDB
L-b,g-Dipalmitoyl-alpha-lecithinHMDB
L-b,g-Dipalmitoyl-alpha-phosphatidylcholineHMDB
L-b,g-DipalmitoylphosphatidylcholineHMDB
L-Dipalmitoyl lecithinHMDB
L-DPPCHMDB
PC Aa C32:0HMDB
sn-3-DipalmitoyllecithinHMDB
1,2-Dipalmitoyl-GPCHMDB
PC(16:0/16:0)Lipid Annotator
1,2-Distearoyl-glycero-3-phosphocholineHMDB
Chemical FormulaC40H80NO8P
Average Molecular Weight734.0389
Monoisotopic Molecular Weight733.562155053
IUPAC Name(2-{[(2R)-2,3-bis(hexadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2,3-bis(hexadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number63-89-8
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C40H80NO8P/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/h38H,6-37H2,1-5H3/t38-/m1/s1
InChI KeyKILNVBDSWZSGLL-KXQOOQHDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentPhosphatidylcholines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic salt
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process