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Showing Compound PC(16:0/16:0) (FDB022121)

Record Information
Version1.0
Creation date2011-09-21 00:08:47 UTC
Update date2020-02-24 19:11:11 UTC
Primary IDFDB022121
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. [HMDB]
CAS Number63-89-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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-phosphocholineLipid Annotator, HMDB
LecithinLipid Annotator, HMDB
PC(16:0/16:0)Lipid Annotator
1,2-dihexadecanoyl-rac-glycero-3-phosphocholineLipid Annotator, HMDB
GPCho(32:0)Lipid Annotator, 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
1,2-Distearoyl-glycero-3-phosphocholineHMDB
(R)-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-apentacosan-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-apentacosan-1-aminium 4-oxide 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 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
1-16:0-2-16:0-AtidylcholineChEBI
1,2-Bis(hexadecanoyl)-sn-glycero-3-ocholineChEBI
1,2-Bis(palmitoyl)-sn-glycero-3-ocholineHMDB
1,2-Dihexadecanoyl-sn-glycero-3-ocholineChEBI
1,2-Dihexadecanoyl-sn-glycerol-3-orylcholineHMDB
1,2-Dipalmitoyl-3-sn-atidylcholineHMDB
1,2-Dipalmitoyl-L-3-atidylcholineHMDB
1,2-Dipalmitoyl-L-a-atidylcholineHMDB
1,2-Dipalmitoyl-L-alpha-atidylcholineHMDB
1,2-Dipalmitoyl-L-atidylcholineHMDB
1,2-Dipalmitoyl-rac-glycero-3-ocholineHMDB
1,2-Dipalmitoyl-sn-3-glyceroocholineHMDB
1,2-Dipalmitoyl-sn-atidylcholineHMDB
1,2-Dipalmitoyl-sn-glycero-3-atidylcholineChEBI
1,2-Dipalmitoyl-sn-glycero-3-ocholineChEBI
1,2-Dipalmitoyl-sn-glycero-3-orylcholineHMDB
1,2-Dipalmitoyl-sn-glycerol-3-ocholineHMDB
1,2-Dipalmitoyl-sn-glyceroocholineHMDB
1,2-Dipalmitoyl-sn-glyceroorylcholineHMDB
1,2-Dipalmitoyl-sn-glyceryl-3-ocholineHMDB
1,2-DipalmitoylatidylcholineChEBI
1,2-Dipalmitoylglycero-3-ocholineHMDB
1,2-Dipalmitoylglycero-3-phosphocholinehmdb
1,2-L-a-DipalmitoylatidylcholineHMDB
1,2-L-alpha-DipalmitoylatidylcholineHMDB
Atidylcholine 16:0/16:0ChEBI
Atidylcholine(16:0/16:0)ChEBI
Atidylcholine(32:0)ChEBI
b,g-Dipalmitoyl L-a-atidylcholineHMDB
b,g-Dipalmitoyl L-alpha-atidylcholineHMDB
b,g-Dipalmitoyl-L-atidylcholineHMDB
Dihexadecanoyl-sn-glycero-3-ocholineHMDB
Dipalmitoyl atidylcholineChEBI
Dipalmitoyl L-a-atidylcholineHMDB
Dipalmitoyl L-alpha-atidylcholineHMDB
Dipalmitoyl-L-3-glycerylorylcholineHMDB
Dipalmitoyl-L-a-atidylcholineHMDB
Dipalmitoyl-L-alpha-atidylcholineHMDB
Dipalmitoyl-sn-3-atidylcholineHMDB
DipalmitoylatidylcholineChEBI
L-1,2-DipalmitoylatidylcholineHMDB
L-a-DipalmitoylatidylcholineHMDB
L-alpha-DipalmitoylatidylcholineHMDB
L-b,g-Dipalmitoyl-a-atidylcholineHMDB
L-b,g-Dipalmitoyl-alpha-atidylcholineHMDB
L-b,g-DipalmitoylatidylcholineHMDB
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC40H80NO8P
IUPAC name(2-{[(2R)-2,3-bis(hexadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
InChI IdentifierInChI=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
Isomeric SMILES[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC
Average Molecular Weight734.0389
Monoisotopic Molecular Weight733.562155053
Classification
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

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - IT 40V, negativesplash10-066r-0060100900-b6bff2ff205808890e0b2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 1V, positivesplash10-001i-0900000000-455598e8d7de92b66a2d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 1V, positivesplash10-0udi-0000290000-79bb58a12a550b7285842020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - IT 30V, positivesplash10-001i-0900000400-ed1d6ef09691e9bb1b3e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-001i-0000000900-012345aef55bfeb672012020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-004j-0000900000-208fe5d1fc5dcb9e17872020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-0002-0000029000-0cc983f3015a15000bcb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 23V, positivesplash10-001r-0000000900-fa22d7b44b6ecf7bf3cb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 33V, positivesplash10-001i-0500000900-6608b50815a9b5d35f042020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 51V, positivesplash10-001i-0900000000-9afadd11d3d3f123032d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 68V, positivesplash10-001i-2900000000-ce1e31a52e9cb1245e692020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 85V, positivesplash10-001r-4900000000-d399948e3d53f292acf42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 124V, positivesplash10-0079-9800000000-58fcb9ea0920120df2542020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 137V, positivesplash10-0079-9700000000-1bd1b9fb29d82e116b292020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 162V, positivesplash10-007a-9600000000-f4a52586e5510140e9942020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 189V, positivesplash10-0072-9400000000-494bd7a2e515e6c62d172020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 223V, positivesplash10-0002-9100000000-548cf59f4be7b55dd9422020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 258V, positivesplash10-0002-9000000000-852b94593bcfb0db899c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 309V, positivesplash10-0002-9000000000-1c426c57d21ff7447e742020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-002k-0000900200-dfdc7f3a135b074862482020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-014i-0000900000-875312e72ac68920d8df2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-01q9-0980000000-e120b0535f2910e5dbe82020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-e904df388d2d70397c9f2017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000900-18b2f9e577dc5a9bfcb82017-10-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900211200-e76cb9b9e105ad69b5702017-10-04View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
ChemSpider ID398235
ChEMBL IDCHEMBL1200737
KEGG Compound IDC00157
Pubchem Compound ID452110
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00564
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDPCF
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDipalmitoylphosphatidylcholine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
2-acylglycerol O-acyltransferase 2MOGAT2Q3SYC2
Phospholipase D2PLD2O14939
Choline-phosphate cytidylyltransferase BPCYT1BQ9Y5K3
Choline-phosphate cytidylyltransferase APCYT1AP49585
Choline kinase alphaCHKAP35790
Phospholipase D3PLD3Q8IV08
Phospholipase D4PLD4Q96BZ4
Phospholipase D6PLD6Q8N2A8
Lecithin retinol acyltransferaseLRATO95237
Phosphatidylserine synthase 1PTDSS1P48651
Eosinophil lysophospholipaseCLCQ05315
Neuropathy target esterasePNPLA6Q8IY17
Phosphatidylcholine:ceramide cholinephosphotransferase 2SGMS2Q8NHU3
Phosphatidylcholine:ceramide cholinephosphotransferase 1SGMS1Q86VZ5
Acyl-protein thioesterase 1LYPLA1O75608
Acyl-protein thioesterase 2LYPLA2O95372
Phosphatidylcholine-sterol acyltransferaseLCATP04180
Lysophospholipid acyltransferase 5LPCAT3Q6P1A2
Lysophosphatidylcholine acyltransferase 2LPCAT2Q7L5N7
Phosphatidylethanolamine-binding protein 1PEBP1P30086
Phosphatidylethanolamine-binding protein 4PEBP4Q96S96
Pathways
NameSMPDB LinkKEGG Link
Phospholipid BiosynthesisSMP00025 map00564
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference