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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 09:39:52 UTC
HMDB IDHMDB0000564
Secondary Accession Numbers
  • HMDB0000804
  • HMDB0005250
  • HMDB0007968
  • HMDB00564
  • HMDB00804
  • HMDB05250
  • HMDB07968
Metabolite Identification
Common NamePC(16:0/16:0)
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
Thumb
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
(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-rac-glycero-3-phosphocholineHMDB
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
gpcho(32:0)HMDB
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
LecithinHMDB
PC Aa C32:0HMDB
sn-3-DipalmitoyllecithinHMDB
PC(16:0/16:0)Lipid Annotator
1,2-dihexadecanoyl-rac-glycero-3-phosphocholineLipid Annotator
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
DescriptionThis compound 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

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.4e-05 g/LALOGPS
logP5.29ALOGPS
logP8.11ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area111.19 ŲChemAxon
Rotatable Bond Count40ChemAxon
Refractivity215.87 m³·mol⁻¹ChemAxon
Polarizability92 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-e904df388d2d70397c9fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000900-18b2f9e577dc5a9bfcb8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900211200-e76cb9b9e105ad69b570View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified584.557 +/- 134.506 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified13.6 (11.8-15.7) uMInfant (0-1 year old)Not Available
Normal
details
BloodDetected and Quantified13.87 (0.11-42.20) uMAdolescent (13-18 years old)Both
Normal
details
BloodDetected and Quantified8.50-30.0 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified15.3 (12.7-18.3) uMNewborn (0-30 days old)Not Available
Normal
details
BloodDetected and Quantified15.1 +/- 3.01 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.198 +/- 0.349 uMAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified0.0035 (0.0013-0.0071) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0038 +/- 0.0081 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified17.85 (12.57-49.03) uMAdolescent (13-18 years old)Both
Pain or fever
details
BloodDetected and Quantified11.830 (10.249) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified21.468 (6.561) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified20.56 (12.79-46.67) uMAdolescent (13-18 years old)Both
Acetaminophen overdose
details
BloodDetected and Quantified10.6 +/- 2.7 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified12.5 +/- 3.2 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
FecesDetected but not Quantified Newborn (0-30 days old)Not Specified
Premature neonates
details
UrineDetected and Quantified0.0026 +/- 0.0025 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.0035 +/- 0.0065 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood214.738 +/- 57.817 uMAdult (>18 years old)BothNormal (Most Probable)Calculated using MetaboAnalyst
Blood584.550 +/- 134.486 uMAdult (>18 years old)BothNormal (Upper Limit)Calculated using MetaboAnalyst
Associated Disorders and Diseases
Disease References
Pregnancy
  1. Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Obesity
  1. Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDDB09114
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022121
KNApSAcK IDNot Available
Chemspider ID398235
KEGG Compound IDC00157
BioCyc ID1-2-DIPALMITOYLPHOSPHATIDYLCHOLINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5548
PubChem Compound452110
PDB IDPCF
ChEBI ID72999
References
Synthesis ReferenceBouirig, H.; Eloy, D.; Jardon, P. Formation and reactivity of the singlet oxygen photosensitized by hypericin in the liposomes of dipalmitoylphosphatidylcholine. Evidence of delayed oxidation. Journal de Chimie Physique et de Physico-Chimie Biologique (1992), 89(6), 1391-411.
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Only showing the first 10 proteins. There are 78 proteins in total.

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has depalmitoylating activity and also low lysophospholipase activity.
Gene Name:
LYPLA1
Uniprot ID:
O75608
Molecular weight:
24669.355
General function:
Involved in phosphatidylcholine-sterol O-acyltransferase activity
Specific function:
Has transacylase and calcium-independent phospholipase A2 activity. Catalyzes the formation of 1-O-acyl-N-acetylsphingosine and the concomitant release of a lyso-phospholipid (By similarity). May have weak lysophospholipase activity.
Gene Name:
PLA2G15
Uniprot ID:
Q8NCC3
Molecular weight:
Not Available
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. This isozyme hydrolyzes more efficiently L-alpha-1-palmitoyl-2-oleoyl phosphatidylcholine than L-alpha-1-palmitoyl-2-arachidonyl phosphatidylcholine, L-alpha-1-palmitoyl-2-arachidonyl phosphatidylethanolamine, or L-alpha-1-stearoyl-2-arachidonyl phosphatidylinositol. May be involved in the production of lung surfactant, the remodeling or regulation of cardiac muscle.
Gene Name:
PLA2G5
Uniprot ID:
P39877
Molecular weight:
15674.065
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Hydrolyzes phosphatidylglycerol versus phosphatidylcholine with a 15-fold preference.
Gene Name:
PLA2G2F
Uniprot ID:
Q9BZM2
Molecular weight:
23256.29
General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular weight:
85210.19
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Molecular weight:
16359.535
General function:
Involved in phospholipase A2 activity
Specific function:
Not known; does not seem to have catalytic activity.
Gene Name:
PLA2G12B
Uniprot ID:
Q9BX93
Molecular weight:
Not Available
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:
PLA2G10
Uniprot ID:
O15496
Molecular weight:
18153.04
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Molecular weight:
15988.525
General function:
Involved in hydrolase activity
Specific function:
May hydrolyze fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has lysophospholipase activity (By similarity). Deacylates GAP43.
Gene Name:
LYPLA2
Uniprot ID:
O95372
Molecular weight:
24736.71

Transporters

General function:
Involved in ATP binding
Specific function:
Mediates ATP-dependent export of organic anions and drugs from the cytoplasm. Hydrolyzes ATP with low efficiency. Human MDR3 is not capable of conferring drug resistance. Mediates the translocation of phosphatidylcholine across the canalicular membrane of the hepatocyte
Gene Name:
ABCB4
Uniprot ID:
P21439
Molecular weight:
141521.8

Only showing the first 10 proteins. There are 78 proteins in total.