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PC(18:1(9Z)/18:1(9Z)) (YMDB01191)

Identification
YMDB IDYMDB01191
NamePC(18:1(9Z)/18:1(9Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(18:1(9Z)/18:1(9Z)) 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(18:1(9Z)/18:1(9Z)), in particular, consists of two 9Z-octadecenoyl 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-Diacyl-sn-glycero-3-phosphocholine
  • 1,2-diacyl-sn-glycero-3-phosphocholines
  • 1,2-Dioleoyl-L-alpha-lecithin
  • 1,2-dioleoyl-L-alpha-phosphatidylcholine
  • 1,2-dioleoyl-rac-glycero-3-phosphocholine
  • 1,2-DIOLEOYL-SN-GLYCERO-3-PHOSPHOCHOLINE
  • 1,2-Dioleoylglycerol-3-phosphorylcholine
  • 1,2-Dioleoylglyceryl-3-phosphorylcholine
  • 1,2-Dioleoyllec
  • 3-sn-Phosphatidylcholine
  • Choline phosphatide
  • Dioleoyl phosphatidylcholine
  • dioleoyllecithin
  • Dioleoylphosphatidylcholine
  • DOPC
  • GPCho(18:1/18:1)
  • GPCho(18:1n9/18:1n9)
  • GPCho(18:1w9/18:1w9)
  • GPCho(36:2)
  • L-alpha-phosphatidylcholine
  • Lecithin
  • lecithins
  • PC
  • PC(18:1/18:1)
  • PC(18:1n9/18:1n9)
  • PC(18:1w9/18:1w9)
  • PC(36:2)
  • Phosphatidyl-N-trimethylethanolamine
  • Phosphatidylcholine
  • Phosphatidylcholine(18:1/18:1)
  • Phosphatidylcholine(18:1n9/18:1n9)
  • Phosphatidylcholine(18:1w9/18:1w9)
  • Phosphatidylcholine(36:2)
  • (R-(Z,Z))-(7-Oleoyl-4-oxido-10-oxo-3,5,9-trioxa-4-phosphaheptacos-18-enyl)trimethylammonium 4-oxide
  • 1,2-Di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
  • 1-(9Z)-Octadecenoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine
  • 1-C18:1(Omega-9)-2-C18:1(omega-9)-phosphatidylcholine
  • Dioleoyl lecithin
  • PC 18:1
  • PC(18:1(9Z)/18:1(9Z))
  • Phosphatidylcholine 18:1
  • 1,2-Dioleoyl-L-a-lecithin
  • 1,2-Dioleoyl-L-α-lecithin
  • 1,2-Di-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine
  • 1,2-Dioleoyl-sn-glycerol-3-ethylphosphocholine
  • Dioleylphosphatidylcholine
  • 1,2-Oleoylphosphatidylcholine, (L-alpha)-(R-(Z,Z))-isomer
  • Dielaidoylphosphatidylcholine
  • 1,2-Dioleoylglycerophosphocholine
  • 1,2-Oleoyl-sn-glycero-3-phosphocholine
  • Dielaidinoyl lecithin
  • 1,2-DOCPC
  • 1,2-Dioleoyl glycerophosphocholine
  • 1,2-Oleoylphosphatidylcholine
  • 1,2-Dioleoyl-GPC
  • 1,2-Dioleoyl-sn-glycero-phosphatidylcholine
  • GPC(18:1(9Z)/18:1(9Z))
  • GPC(18:1/18:1)
  • GPC(18:1n9/18:1n9)
  • GPC(18:1w9/18:1w9)
  • GPC(36:2)
  • GPCho(18:1(9Z)/18:1(9Z))
  • Phosphatidylcholine(18:1(9Z)/18:1(9Z))
  • 1,2-Dioleoyl-3-sn-phosphatidylcholine
  • 1,2-Dioleoyl-sn-glycero-3-phosphochline
  • 1,2-Dioleoyl-sn-glycero-3-phosphorylcholine
  • 1,2-Dioleoyl-sn-phosphatidylcholine
  • 1,2-Dioleoylphosphatidylcholine
  • 1,2-Dioleyl-L-lecithin
  • Dioleoyl L-alpha-lecithin
  • Dioleoyl L-α-lecithin
  • Dioleoyl-3-sn-phosphatidylcholine
  • Dioleoyl-L-alpha-glycerophosphocholine
  • Dioleoyl-L-alpha-glycerophosphorylcholine
  • Dioleoyl-L-alpha-phosphatidylcholine
  • Dioleoyl-L-α-glycerophosphocholine
  • Dioleoyl-L-α-glycerophosphorylcholine
  • Dioleoyl-L-α-phosphatidylcholine
  • L-Dioleoyl lecithin
  • L-Dioleoylphosphatidylcholine
  • L-alpha-Di(cis-9-octadecanoyl) lecithin
  • L-alpha-Dioleoyl phosphatidylcholine
  • L-alpha-Dioleoyllecithin
  • L-alpha-Dioleylphosphatidylcholine
  • L-α-Di(cis-9-octadecanoyl) lecithin
  • L-α-Dioleoyl phosphatidylcholine
  • L-α-Dioleoyllecithin
  • L-α-Dioleylphosphatidylcholine
  • sn-3-Dioleoyllecithin
  • 1,2-Dioleoyllecithin
  • Dioleoylglycerophosphocholine
  • Dioleoylglycerophosphorylcholine
  • Dioleoylglycerylphosphorylcholine
  • Dioleyl lecithin
  • Dioleyl phosphatidylcholine
CAS number68737-67-7
WeightAverage: 786.1134
Monoisotopic: 785.593455181
InChI KeySNKAWJBJQDLSFF-NVKMUCNASA-N
InChIInChI=1S/C44H84NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h20-23,42H,6-19,24-41H2,1-5H3/b22-20-,23-21-/t42-/m1/s1
IUPAC Name(2-{[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Chemical FormulaC44H84NO8P
SMILESCCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC
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 Solubility2.2e-05 g/LALOGPS
logP5.78ALOGPS
logP9.17ChemAxon
logS-7.6ALOGPS
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 Count42ChemAxon
Refractivity236.5 m³·mol⁻¹ChemAxon
Polarizability96.97 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • endoplasmic reticulum
Organoleptic PropertiesNot Available
SMPDB Pathways
Glycerophospholipid metabolismPW002493 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into ER PC(18:1(9Z)/18:1(9Z))PW002788 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into Mitochondria PC(18:1(9Z)/18:1(9Z))PW002796 ThumbThumb?image type=greyscaleThumb?image type=simple
Phosphatidylcholine biosynthesis PC(18:1(9Z)/18:1(9Z))PW002941 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
Citicoline + DG(18:1(9Z)/18:1(9Z)/0:0) → Cytidine monophosphate + hydron + PC(18:1(9Z)/18:1(9Z))
PC(18:1(9Z)/0:0) → PC(18:1(9Z)/18:1(9Z))
PE-NMe2(18:1(9Z)/18:1(9Z)) + S-Adenosyl-L-methionine → S-Adenosylhomocysteine + hydron + PC(18:1(9Z)/18:1(9Z))
KEGG Reactions
Citicoline + 1,2-dioleoylglycerol ↔ PC(18:1(9Z)/18:1(9Z)) + Cytidine monophosphate
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
0.755 ± 0.03775 µM YEB media with 0.5 mM glucoseaerobicBrewer's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000900-36f689a3cf8b031c9ce5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-0600000900-4df68b8e85813f4b5ad8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1900021300-f15a88b3adc3a38193cbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000090-53a8e01f33b2af13f226JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000190-64f46bdfe255d6a5b5e4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004k-0900139110-7365097ffb2d5d55b434JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000900-64c382f846ba04194d31JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000900-6c06686879d9f7790e62JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-0200249400-1ae2411ef15a63cb3b2dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000900-e54f4b7d729e27672b37JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-0600000900-3a2440aaca7e87ec13a5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1900021300-24d60344b49a468b0469JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000900-23df8d3c4971511f3b91JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0050030900-b121f3ff4b078b5df33eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1090200000-673c166236d767f9289eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000090-683d2aaf9f12a9d08614JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0010000090-37042360a3899f1fdc23JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00f0-0090000090-06eeedb644af6eeff7ecJSpectraViewer
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
  • Hjelmstad, R. H., Bell, R. M. (1987). "Mutants of Saccharomyces cerevisiae defective in sn-1,2-diacylglycerol cholinephosphotransferase. Isolation, characterization, and cloning of the CPT1 gene." J Biol Chem 262:3909-3917.3029130
Synthesis Reference:Tokuyama, Satoru; Morisawa, Kazuya; Nakachi, Osamu; Nakano, Yoshiro; Miki, Tomoharu. Preparation of phosphatidylcholines. Jpn. Kokai Tokkyo Koho (1989), 6 pp.
External Links:
ResourceLink
CHEBI ID16110
HMDB IDHMDB00593
Pubchem Compound ID65167
Kegg IDC00157
ChemSpider ID8525772
FOODB IDNot Available
WikipediaLecithin
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.