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Record Information
Version1.0
Creation Date2016-09-30 22:32:52 UTC
Update Date2020-06-04 20:04:17 UTC
BMDB IDBMDB0000564
Secondary Accession Numbers
  • BMDB00564
Metabolite Identification
Common NamePC(16:0/16:0)
DescriptionPC(16:0/16:0), also known as DPPC or 16:0-16:0-PC, 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. Thus, PC(16:0/16:0) is considered to be a glycerophosphocholine lipid molecule. PC(16:0/16:0) exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. PC(16:0/16:0) exists in all eukaryotes, ranging from yeast to humans. In cattle, PC(16:0/16:0) is involved in the metabolic pathway called phospholipid biosynthesis pathway.
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
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
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
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Intracellular membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - IT 40V, negativesplash10-066r-0060100900-b6bff2ff205808890e0bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 1V, positivesplash10-001i-0900000000-455598e8d7de92b66a2dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 1V, positivesplash10-0udi-0000290000-79bb58a12a550b728584View in MoNA
LC-MS/MSLC-MS/MS Spectrum - IT 30V, positivesplash10-001i-0900000400-ed1d6ef09691e9bb1b3eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-001i-0000000900-012345aef55bfeb67201View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-004j-0000900000-208fe5d1fc5dcb9e1787View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-0002-0000029000-0cc983f3015a15000bcbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 23V, positivesplash10-001r-0000000900-fa22d7b44b6ecf7bf3cbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 33V, positivesplash10-001i-0500000900-6608b50815a9b5d35f04View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 51V, positivesplash10-001i-0900000000-9afadd11d3d3f123032dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 68V, positivesplash10-001i-2900000000-ce1e31a52e9cb1245e69View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 85V, positivesplash10-001r-4900000000-d399948e3d53f292acf4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 124V, positivesplash10-0079-9800000000-58fcb9ea0920120df254View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 137V, positivesplash10-0079-9700000000-1bd1b9fb29d82e116b29View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 162V, positivesplash10-007a-9600000000-f4a52586e5510140e994View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 189V, positivesplash10-0072-9400000000-494bd7a2e515e6c62d17View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 223V, positivesplash10-0002-9100000000-548cf59f4be7b55dd942View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 258V, positivesplash10-0002-9000000000-852b94593bcfb0db899cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 309V, positivesplash10-0002-9000000000-1c426c57d21ff7447e74View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-002k-0000900200-dfdc7f3a135b07486248View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-014i-0000900000-875312e72ac68920d8dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-01q9-0980000000-e120b0535f2910e5dbe8View in MoNA
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
  • Cell membrane
  • Cytoplasm
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • Milk
  • Placenta
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected and Quantified10.4 +/- 0.4 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified12.5 +/- 0.5 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified15.1 +/- 0.3 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified10.2 +/- 0.3 uMNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified0.040 +/- 0.03 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000564
DrugBank IDDB09114
Phenol Explorer Compound IDNot Available
FooDB IDFDB022121
KNApSAcK IDNot Available
Chemspider ID398235
KEGG Compound IDC00157
BioCyc ID1-2-DIPALMITOYLPHOSPHATIDYLCHOLINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5548
PubChem Compound452110
PDB IDNot Available
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)Not Available
General References
  1. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Catalyzes phosphatidylcholine biosynthesis from CDP-choline. It thereby plays a central role in the formation and maintenance of vesicular membranes (By similarity).
Gene Name:
CHPT1
Uniprot ID:
Q1LZE6
Molecular weight:
45249.0
Reactions
Citicoline → PC(16:0/16:0) + DG(16:0/16:0/0:0)details
General function:
Involved in phosphatidylethanolamine N-methyltransferas
Specific function:
Catalyzes the three sequential steps of the methylation pathway of phosphatidylcholine biosynthesis, the SAM-dependent methylation of phosphatidylethanolamine (PE) to phosphatidylmonomethylethanolamine (PMME), PMME to phosphatidyldimethylethanolamine (PDME), and PDME to phosphatidylcholine (PC).
Gene Name:
PEMT
Uniprot ID:
Q7YRH6
Molecular weight:
22018.0
Reactions
S-Adenosylmethionine + PE-NMe2(16:0/16:0) → S-Adenosylhomocysteine + PC(16:0/16:0)details
PE(16:0/16:0) → PC(16:0/16:0)details
General function:
Not Available
Specific function:
Catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Thought to participate in the regulation of phospholipid metabolism in biomembranes including eicosanoid biosynthesis. Independent of its catalytic activity, acts as a ligand for integrins. Binds to and activates integrins ITGAV:ITGB3, ITGA4:ITGB1 and ITGA5:ITGB1. Binds to a site (site 2) which is distinct from the classical ligand-binding site (site 1) and induces integrin conformational changes and enhanced ligand binding to site 1. Induces cell proliferation in an integrin-dependent manner.
Gene Name:
PLA2G2A
Uniprot ID:
Q56JZ2
Molecular weight:
16347.0
Reactions
PC(16:0/16:0) → LysoPC(16:0/0:0)details