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PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (YMDB15898)

Identification
YMDB IDYMDB15898
NamePC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) 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(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)), in particular, consists of two 5Z,8Z,11Z,14Z-eicosatetraenoyl 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
  • 1,2-Di-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholine
  • 1,2-Diarachidonoyl-glycero-3-phosphocholine
  • 1,2-Diarachidonoyl-sn-glycero-3-phosphocholine
  • 1,2-Diarachidonyl-L-alpha-glycerophosphorylcholine
  • 1,2-Diarachidonylphosphatidylcholine
  • 1,2-Diarachidyl-3-phosphatidylcholine
  • DAPC
  • Diarachidonoylphosphatidylcholine
  • Diarachidonyl lecithin
  • Diarachidonyl phosphatidylcholine
  • PC(20:4/20:4)
  • 1,2-Diarachidonyl-L-a-glycerophosphorylcholine
  • 1,2-Diarachidonyl-L-α-glycerophosphorylcholine
  • 1,2-Diradyl-3-phosphatidylcholine
  • PC(40:8)
  • Phosphatidylcholine(20:4/20:4)
  • Phosphatidylcholine(40:8)
  • Lecithin
  • GPCho(20:4/20:4)
  • GPCho(40:8)
  • 1,2-Di(5Z,8Z,11Z,14Z-eicosatetraenoyl)-rac-glycero-3-phosphocholine
  • 1,2-Diarachidonoyl-rac-glycero-3-phosphocholine
  • PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))
CAS numberNot Available
WeightAverage: 830.1245
Monoisotopic: 829.562155053
InChI KeyLZLVZIFMYXDKCN-QJWFYWCHSA-N
InChIInChI=1S/C48H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-47(50)54-44-46(45-56-58(52,53)55-43-42-49(3,4)5)57-48(51)41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h14-17,20-23,26-29,32-35,46H,6-13,18-19,24-25,30-31,36-45H2,1-5H3/b16-14-,17-15-,22-20-,23-21-,28-26-,29-27-,34-32-,35-33-/t46-/m1/s1
IUPAC Name(2-{[(2R)-2,3-bis[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Namediarachidonyl lecithin
Chemical FormulaC48H80NO8P
SMILESCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
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 pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.5e-05 g/LALOGPS
logP5.67ALOGPS
logP8.77ChemAxon
logS-7.4ALOGPS
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
Refractivity261.61 m³·mol⁻¹ChemAxon
Polarizability96.81 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
  • Mitochondria
Organoleptic PropertiesNot Available
SMPDB Pathways
Lysolipid incorporation into ER PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))PW002790 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into Mitochondria PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))PW002798 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
Citicoline + DG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/0:0) → Cytidine monophosphate + hydron + PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))
LysoPC(20:4(5Z,8Z,11Z,14Z)) → PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))
PE-NMe2(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) + S-Adenosyl-L-methionine → S-Adenosylhomocysteine + hydron + PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000090-6b9fc011848cc9c89204JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000090-2474fb0095b51b5e823cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900021120-30b28ce182d3bfa88618JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000090-1023bafff7fb8b4a46bfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000000190-4a5c55b4ef6aa69ab843JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0200249220-3e420ddb8f3c8ca82ebbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000090-1057516eaf51445afea3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000090-4e0b1f0b79372e5fc6ffJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900021120-f5d410d0c1a5a7185826JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000090-fa2bf6c3c89cea47a840JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-0019003370-d8343fee5bbc7220870dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-5159000000-e5e506b5c3be8c4eb282JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-f258085e9de304c2430eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0001000090-dfd14407121a66f239c0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0xr0-0009000090-55d3d9096b601785849dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000090-cb15d5da1da59dd58588JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000190-ee3451433bac9c082aa2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014k-0900139110-925d5702488a0492b2adJSpectraViewer
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:
  • Rattray JB, Schibeci A, Kidby DK. (1975). "Lipids of yeasts." Bacteriol Rev. 1975 Sep;39(3):197-231.240350
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID60657
HMDB IDHMDB0008443
Pubchem Compound ID24779076
Kegg IDNot Available
ChemSpider IDNot Available
FOODB IDFDB025633
Wikipedia IDNot Available
BioCyc IDNot Available

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.