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Identification
YMDB IDYMDB01175
NamePC(14:0/0:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionLysoPC(14:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(14:0), in particular, consists of one chain of myristic acid at the C-1 position. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling.
Structure
Thumb
Synonyms
  • 1-acyl-2-lyso-phosphatidylcholine
  • 1-Acyl-sn-glycero-3-phosphocholine
  • 1-acyl-sn-glycero-3-phosphocholines
  • 1-Acyl-sn-glycerol-3-phosphocholine
  • 1-Acylglycerophosphocholine
  • 1-myristoyl-glycero-3-phosphocholine
  • 2-Lysolecithin
  • 2-Lysophosphatidylcholine
  • alpha-Acylglycerophosphocholine
  • LPC
  • LPC(14:0)
  • LPC(14:0/0:0)
  • LyPC(14:0)
  • LyPC(14:0/0:0)
  • LysoPC(14:0)
  • LysoPC(14:0/0:0)
  • Lysophosphatidylcholine(14:0)
  • Lysophosphatidylcholine(14:0/0:0)
  • 1-C14:0-Lysophosphatidylcholine betaine
  • 1-Myristoyl-sn-glycero-3-phosphocholine betaine
  • 1-Tetradecanoyl-sn-glycero-3-phosphocholine
  • 1-Tetradecanoyl-sn-glycero-3-phosphocholine betaine
  • PC(14:0/0:0)
  • 1-tetradecanoyl-glycero-3-phosphocholine
  • 1-Myristoylglycerophosphocholine
  • 1-Tetradecanoylglycerophosphocholine
  • 1-Myristoyl-GPC
  • 1-Myristoyl-lysophosphatidylcholine
  • 1-Myristoyl-sn-glycero-3-phosphocholine
  • GPC(14:0)
  • GPC(14:0/0:0)
CAS numberNot Available
WeightAverage: 467.5769
Monoisotopic: 467.301189343
InChI KeyVXUOFDJKYGDUJI-OAQYLSRUSA-N
InChIInChI=1S/C22H46NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-22(25)28-19-21(24)20-30-31(26,27)29-18-17-23(2,3)4/h21,24H,5-20H2,1-4H3/t21-/m1/s1
IUPAC Name(2-{[(2R)-2-hydroxy-3-(tetradecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[(2R)-2-hydroxy-3-(tetradecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Chemical FormulaC22H46NO7P
SMILES[H][C@@](O)(COC(=O)CCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-acyl-sn-glycero-3-phosphocholines
Alternative Parents
Substituents
  • 1-acyl-sn-glycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic salt
  • Amine
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00075 g/LALOGPS
logP1.1ALOGPS
logP0.3ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area105.12 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity133.07 m³·mol⁻¹ChemAxon
Polarizability53.74 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Lysolipid incorporation into MitochondriaPW002531 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into Mitochondria PC(14:0/14:0)PW002792 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into Mitochondria PC(16:1(11Z)/16:1(11Z))PW002794 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into Mitochondria PC(18:2(9Z,11Z)/18:2(9Z,11Z))PW002797 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerophospholipid metabolismec00564 Map00564
SMPDB Reactions
PC(14:0/0:0) + waterGlycerophosphocholine + a carboxylate
PC(14:0/0:0)PC(14:0/14:0)
PC(14:0/0:0)PC(16:1(11Z)/16:1(11Z))
PC(14:0/0:0)PC(18:2(9Z,11Z)/18:2(9Z,11Z))
Adenosine triphosphate + water + PC(14:0/0:0)ADP + phosphate + PC(14:0/0:0)
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0230-9411000000-7a6b8e8fd1e0609b417eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000900000-c557e23aa67a6a68e471JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0000900000-89cc0e21e01554e310d6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pcr-1617900000-231c7760e10f0c81e04bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000390000-b1814b140293d64c3417JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-0090160000-48fcbf8694eed693a211JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0090110000-c40c1368f5389cd115f2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0000900000-534f405ea851fa87d3e5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-0900600000-9a2a86225de12cddb6bdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-0910400000-63d03888aa82a44da515JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0030900000-648928c7aa526a1c5514JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090100000-6eecefd72f10fda6c57aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0090000000-aaa1334bcdf77ff34dd1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000900000-56c0d0685c46c9ba6fe3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01i0-0010900000-50babd7089582cb56ec8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0frl-0390400000-26a01ba41c58e985ad7cJSpectraViewer
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
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:Not Available
External Links:
ResourceLink
CHEBI ID17504
HMDB IDHMDB10379
Pubchem Compound ID14420997
Kegg IDC04230
ChemSpider ID405289
FOODB IDFDB027530
WikipediaLecithin
BioCyc IDPHOSPHATIDYLCHOLINE

Enzymes

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.

Transporters

General function:
Involved in nucleotide binding
Specific function:
This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of phospholipids. Required for protein transport from Golgi to vacuoles
Gene Name:
DNF2
Uniprot ID:
Q12675
Molecular weight:
182617.0
Reactions
ATP + H(2)O + phospholipid(In) → ADP + phosphate + phospholipid(Out).
General function:
Involved in nucleotide binding
Specific function:
This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of phospholipids (Potential)
Gene Name:
DNF1
Uniprot ID:
P32660
Molecular weight:
177796.0
Reactions
ATP + H(2)O + phospholipid(In) → ADP + phosphate + phospholipid(Out).