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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
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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
  • 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
  • 1,2-Oleoylphosphatidylcholine, (e,e)-isomer
  • Dioleylphosphatidylcholine
  • 1,2-Oleoylphosphatidylcholine, (L-alpha)-(R-(Z,Z))-isomer
  • 1,2-Oleoylphosphatidylcholine, 14C-labeled, (R-(Z,Z))-isomer
  • Dielaidoylphosphatidylcholine
  • 1,2-Dioleoylglycerophosphocholine
  • 1,2-Oleoyl-sn-glycero-3-phosphocholine
  • 1,2-Oleoylphosphatidylcholine, (R-(e,e))-isomer
  • 1,2-Oleoylphosphatidylcholine, (Z,Z)-(+-)-isomer
  • Dielaidinoyl lecithin
  • 1,2-DOCPC
  • 1,2-Dioleoyl glycerophosphocholine
  • 1,2-Oleoylphosphatidylcholine
  • PC(18:1(9Z)/18:1(9Z))
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 phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Namedioleoyl phosphatidylcholine
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
Polarizability97.17 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-methionineS-Adenosylhomocysteine + hydron + PC(18:1(9Z)/18:1(9Z))
KEGG Reactions
Citicoline + 1,2-dioleoylglycerolPC(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
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

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.
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.