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PC(16:0/16:0) (YMDB01180)

Identification
YMDB IDYMDB01180
NamePC(16:0/16:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(16:0/16:0) is a phosphatidylchloline (PC). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylcholines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PC(16:0/16:0), in particular, consists of two hexadecanoyl chains at positions C-1 and C-2. In E. coli, PCs can be found in the integral component of the cell outer membrane. They are hydrolyzed by Phospholipases to a 2-acylglycerophosphocholine and a carboxylate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (3-sn-phosphatidyl)choline
  • 1,2-Bis(hexadecanoyl)-sn-glycero-3-phosphocholine
  • 1,2-Bis(palmitoyl)-sn-glycero-3-phosphocholine
  • 1,2-Diacyl-sn-glycero-3-phosphocholine
  • 1,2-diacyl-sn-glycero-3-phosphocholines
  • 1,2-Dihexadecanoyl-sn-glycerol-3-phosphorylcholine
  • 1,2-Dipalmitoyl-3-sn-phosphatidylcholine
  • 1,2-Dipalmitoyl-L-3-phosphatidylcholine
  • 1,2-Dipalmitoyl-L-a-lecithin
  • 1,2-Dipalmitoyl-L-a-phosphatidylcholine
  • 1,2-Dipalmitoyl-L-alpha-lecithin
  • 1,2-Dipalmitoyl-L-alpha-phosphatidylcholine
  • 1,2-Dipalmitoyl-L-lecithin
  • 1,2-Dipalmitoyl-L-phosphatidylcholine
  • 1,2-dipalmitoyl-rac-glycero-3-phosphocholine
  • 1,2-Dipalmitoyl-sn-3-glycerophosphocholine
  • 1,2-Dipalmitoyl-sn-glycero-3-phosphatidylcholine
  • 1,2-Dipalmitoyl-sn-glycero-3-phosphocholine
  • 1,2-Dipalmitoyl-sn-glycero-3-phosphorylcholine
  • 1,2-Dipalmitoyl-sn-glycerol-3-phosphocholine
  • 1,2-Dipalmitoyl-sn-glycerophosphocholine
  • 1,2-Dipalmitoyl-sn-glycerophosphorylcholine
  • 1,2-Dipalmitoyl-sn-glyceryl-3-phosphocholine
  • 1,2-Dipalmitoyl-sn-phosphatidylcholine
  • 1,2-Dipalmitoylglycero-3-phosphocholine
  • 1,2-L-a-Dipalmitoylphosphatidylcholine
  • 1,2-L-alpha-Dipalmitoylphosphatidylcholine
  • 3-sn-Phosphatidylcholine
  • b,g-Dipalmitoyl L-a-phosphatidylcholine
  • b,g-Dipalmitoyl L-alpha-phosphatidylcholine
  • b,g-Dipalmitoyl-L-(a)-lecithin
  • b,g-Dipalmitoyl-L-phosphatidylcholine
  • Choline phosphatide
  • Colfosceril palmitate
  • Dihexadecanoyl-sn-glycero-3-phosphocholine
  • Dipalmitoyl L-a-phosphatidylcholine
  • Dipalmitoyl L-alpha-phosphatidylcholine
  • Dipalmitoyl-L-3-glycerylphosphorylcholine
  • Dipalmitoyl-L-a-lecithin
  • Dipalmitoyl-L-a-phosphatidylcholine
  • Dipalmitoyl-L-alpha-lecithin
  • Dipalmitoyl-L-alpha-phosphatidylcholine
  • Dipalmitoyl-sn-3-phosphatidylcholine
  • Dipalmitoylphosphatidylcholine
  • DPPC
  • GPCho(16:0/16:0)
  • GPCho(32:0)
  • L-1,2-Dipalmitoyl-a-lecithin
  • L-1,2-Dipalmitoyl-alpha-lecithin
  • L-1,2-Dipalmitoylphosphatidylcholine
  • L-a-1,2-Dipalmitoyl lecithin
  • L-a-Dipalmitoylecithin
  • L-a-Dipalmitoyllecithin
  • L-a-Dipalmitoylphosphatidylcholine
  • L-a-DPPC
  • L-alpha-1,2-Dipalmitoyl lecithin
  • L-alpha-Dipalmitoylecithin
  • L-alpha-Dipalmitoyllecithin
  • L-alpha-Dipalmitoylphosphatidylcholine
  • L-alpha-DPPC
  • L-alpha-phosphatidylcholine
  • L-b,g-Dipalmitoyl-a-lecithin
  • L-b,g-Dipalmitoyl-a-phosphatidylcholine
  • L-b,g-Dipalmitoyl-alpha-lecithin
  • L-b,g-Dipalmitoyl-alpha-phosphatidylcholine
  • L-b,g-Dipalmitoylphosphatidylcholine
  • L-Dipalmitoyl lecithin
  • L-DPPC
  • Lecithin
  • lecithins
  • PC
  • PC(16:0/16:0)
  • PC(32:0)
  • Phosphatidyl-N-trimethylethanolamine
  • Phosphatidylcholine
  • Phosphatidylcholine(16:0/16:0)
  • Phosphatidylcholine(32:0)
  • sn-3-Dipalmitoyllecithin
  • 1,2-Dipalmitoylphosphatidylcholine
  • 1-16:0-2-16:0-Phosphatidylcholine
  • 16:0-16:0-PC
  • Colfoscerili palmitas
  • Dipalmitoyl phosphatidylcholine
  • Dipalmitoyl-GPC
  • GPC(16:0/16:0)
  • GPCho 16:0/16:0
  • Palmitate de colfosceril
  • Palmitato de colfoscerilo
  • PC 16:0/16:0
  • Phosphatidylcholine 16:0/16:0
  • Colfosceril palmitic acid
  • Palmitic acid de colfosceril
  • 1,2-Dihexadecanoyl-rac-glycero-3-phosphocholine
  • (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 salt
  • (R)-4-Hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacosan-1-aminium 4-oxide inner salt
  • PC Aa C32:0
  • 1,2-Dipalmitoyl-GPC
  • 1,2-Distearoyl-glycero-3-phosphocholine
CAS number63-89-8
WeightAverage: 734.0389
Monoisotopic: 733.562155053
InChI KeyKILNVBDSWZSGLL-KXQOOQHDSA-N
InChIInChI=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
IUPAC Name(2-{[(2R)-2,3-bis(hexadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[(2R)-2,3-bis(hexadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Chemical FormulaC40H80NO8P
SMILESCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC
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
Physical Properties
StateSolid
Charge0
Melting point234 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Choline metabolismPW002494 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycerophospholipid metabolismPW002493 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into ER PC(16:0/16:0)PW002784 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into Mitochondria PC(16:0/16:0)PW002753 ThumbThumb?image type=greyscaleThumb?image type=simple
Phosphatidylcholine biosynthesis PC(16:0/16:0)PW002885 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Arachidonic acid metabolismec00590 Map00590
Glycerophospholipid metabolismec00564 Map00564
Linoleic acid metabolismec00591 Map00591
alpha-Linolenic acid metabolismec00592 Map00592
SMPDB Reactions
PE-NMe2(16:0/16:0) + S-Adenosyl-L-methionine → S-Adenosylhomocysteine + hydron + PC(16:0/16:0)
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
0.067 ± 0.00335 µM YEB media with 0.5 mM glucoseaerobicBrewer's yeastExperimentally Determined
Not Available
28000 ± 3850 umol/L SD media with 2% raffinose24 oCBY4741PMID: 19174513
45250 ± 19650 umol/L SD media with 2% raffinose37 oCBY4741PMID: 19174513
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - IT 40V, negativesplash10-066r-0060100900-b6bff2ff205808890e0bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 1V, positivesplash10-001i-0900000000-455598e8d7de92b66a2dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 1V, positivesplash10-0udi-0000290000-79bb58a12a550b728584JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - IT 30V, positivesplash10-001i-0900000400-ed1d6ef09691e9bb1b3eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-001i-0000000900-012345aef55bfeb67201JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-004j-0000900000-208fe5d1fc5dcb9e1787JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-0002-0000029000-0cc983f3015a15000bcbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 23V, positivesplash10-001r-0000000900-fa22d7b44b6ecf7bf3cbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 33V, positivesplash10-001i-0500000900-6608b50815a9b5d35f04JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 51V, positivesplash10-001i-0900000000-9afadd11d3d3f123032dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 68V, positivesplash10-001i-2900000000-ce1e31a52e9cb1245e69JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 85V, positivesplash10-001r-4900000000-d399948e3d53f292acf4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 124V, positivesplash10-0079-9800000000-58fcb9ea0920120df254JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 137V, positivesplash10-0079-9700000000-1bd1b9fb29d82e116b29JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 162V, positivesplash10-007a-9600000000-f4a52586e5510140e994JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 189V, positivesplash10-0072-9400000000-494bd7a2e515e6c62d17JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 223V, positivesplash10-0002-9100000000-548cf59f4be7b55dd942JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 258V, positivesplash10-0002-9000000000-852b94593bcfb0db899cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 309V, positivesplash10-0002-9000000000-1c426c57d21ff7447e74JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-002k-0000900200-dfdc7f3a135b07486248JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-014i-0000900000-875312e72ac68920d8dfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 51V, positivesplash10-01q9-0980000000-e120b0535f2910e5dbe8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-e904df388d2d70397c9fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000900-18b2f9e577dc5a9bfcb8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900211200-e76cb9b9e105ad69b570JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Ejsing, C. S., Sampaio, J. L., Surendranath, V., Duchoslav, E., Ekroos, K., Klemm, R. W., Simons, K., Shevchenko, A. (2009). "Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry." Proc Natl Acad Sci U S A 106:2136-2141.19174513
Synthesis Reference:Bouirig, 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 Biologiqu
External Links:
ResourceLink
CHEBI ID16110
HMDB IDHMDB00564
Pubchem Compound ID452110
Kegg IDC00157
ChemSpider ID398235
FOODB IDFDB022121
WikipediaDipalmitoylphosphatidylcholine
BioCyc IDPHOSPHATIDYLCHOLINE

Enzymes

Protein Details
1. Cholinephosphotransferase 1
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Involved in protein-dependent process of phospholipid transport to distribute phosphatidyl choline to the lumenal surface. The multiple transmembrane domains and lumenal hydrophilic domains of the cholinephosphotransferase might participate in the transport process
Gene Name:
CPT1
Uniprot ID:
P17898
Molecular weight:
44829.0
Reactions
CDP-choline + 1,2-diacylglycerol → CMP + a phosphatidylcholine.
Protein Details
2. Methylene-fatty-acyl-phospholipid synthase
General function:
Involved in N-methyltransferase activity
Specific function:
S-adenosyl-L-methionine + phospholipid olefinic fatty acid = S-adenosyl-L-homocysteine + phospholipid methylene fatty acid
Gene Name:
OPI3
Uniprot ID:
P05375
Molecular weight:
23150.09961
Reactions
S-adenosyl-L-methionine + phospholipid olefinic fatty acid → S-adenosyl-L-homocysteine + phospholipid methylene fatty acid.
Protein Details
3. Phospholipase D1
General function:
Involved in protein binding
Specific function:
Required for meiosis and spore formation. Seems to be involved in the coordinate induction of late meiotic events. PLD activity is induced under sporulation conditions and seems to be necessary to complete the meiotic cycle, but not for vegetative cell growth
Gene Name:
SPO14
Uniprot ID:
P36126
Molecular weight:
195202.0
Reactions
A phosphatidylcholine + H(2)O → choline + a phosphatidate.
Protein Details
4. Lysophospholipase NTE1
General function:
Involved in metabolic process
Specific function:
Intracellular phospholipase B that catalyzes the double deacylation of phosphatidylcholine (PC) to glycerophosphocholine (GroPCho). Plays an important role in membrane lipid homeostasis. Responsible for the rapid PC turnover in response to inositol, elevated temperatures, or when choline is present in the growth medium
Gene Name:
NTE1
Uniprot ID:
Q04958
Molecular weight:
187131.0
Reactions
2-lysophosphatidylcholine + H(2)O → glycerophosphocholine + a carboxylate.