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PC(16:1(9Z)/16:1(9Z)) (YMDB01185)

Identification
YMDB IDYMDB01185
NamePC(16:1(9Z)/16:1(9Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(16:1(9Z)/16:1(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(16:1(9Z)/16:1(9Z)), in particular, consists of two 9Z-hexadecenoyl 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-Diacyl-sn-glycero-3-phosphocholine
  • 1,2-dipalmitoleoyl-rac-glycero-3-phosphocholine
  • 3-O-sn-Phosphatidyl-L-serine
  • 3-sn-Phosphatidylcholine
  • Choline phosphatide
  • GPCho(16:1/16:1)
  • GPCho(16:1n7/16:1n7)
  • GPCho(16:1w7/16:1w7)
  • GPCho(32:2)
  • Lecithin
  • Lecithins
  • O3-Phosphatidyl-L-serine
  • PC(16:1/16:1)
  • PC(16:1n7/16:1n7)
  • PC(16:1w7/16:1w7)
  • PC(32:2)
  • Phosphatidyl-L-serine
  • phosphatidyl-L-serines
  • Phosphatidyl-N-trimethylethanolamine
  • Phosphatidylcholine
  • Phosphatidylcholine(16:1/16:1)
  • Phosphatidylcholine(16:1n7/16:1n7)
  • Phosphatidylcholine(16:1w7/16:1w7)
  • Phosphatidylcholine(32:2)
  • 1,2-Di-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholine
  • 1,2-Dipalmitoleoyl-sn-glycero-3-phosphorylcholine
  • Dipalmitoleoyl-L-alpha-glycerophosphorylcholine
  • L-Dipalmitoleoyllecithin
  • PC 16:1(9Z)/16:1(9Z)
  • Dipalmitoleoyl-L-a-glycerophosphorylcholine
  • Dipalmitoleoyl-L-α-glycerophosphorylcholine
  • PC Aa C32:2
  • 1,2-Di(9Z-hexadecenoyl)-rac-glycero-3-phosphocholine
  • PC(16:1(9Z)/16:1(9Z))
CAS number8002-43-5
WeightAverage: 730.0071
Monoisotopic: 729.530854925
InChI KeyGPWHCUUIQMGELX-VHQDNGOZSA-N
InChIInChI=1S/C40H76NO8P/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/h16-19,38H,6-15,20-37H2,1-5H3/b18-16-,19-17-/t38-/m1/s1
IUPAC Name(2-{[(2R)-2,3-bis[(9Z)-hexadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC NameL-dipalmitoleoyllecithin
Chemical FormulaC40H76NO8P
SMILESCCCCCC\C=C/CCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCC
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 Solubility2.9e-05 g/LALOGPS
logP5.12ALOGPS
logP7.39ChemAxon
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 Count38ChemAxon
Refractivity218.1 m³·mol⁻¹ChemAxon
Polarizability87.95 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
Glycerophospholipid metabolismPW002493 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into ER PC(16:1(9Z)/16:1(9Z))PW002785 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into Mitochondria PC(16:1(9Z)/16:1(9Z))PW002793 ThumbThumb?image type=greyscaleThumb?image type=simple
Phosphatidylcholine biosynthesis PC(16:1(9Z)/16:1(9Z))PW002868 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(16:1(9Z)/16:1(9Z)/0:0) → Cytidine monophosphate + hydron + PC(16:1(9Z)/16:1(9Z))
PC(16:1(9Z)/0:0) → PC(16:1(9Z)/16:1(9Z))
PE-NMe2(16:1(9Z)/16:1(9Z)) + S-Adenosyl-L-methionine → S-Adenosylhomocysteine + hydron + PC(16:1(9Z)/16:1(9Z))
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-2c3238d389cac738936fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000900-36b81a67e325f0216f8cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900211200-1bc83cd559310c83c10dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fbi-0090000400-6ac2e20ce745f6196fccJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0090001000-6bc9429c31c4de650023JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zi9-4091100000-3e65d04f14832f0c5316JSpectraViewer
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 ID18303
HMDB IDHMDB08002
Pubchem Compound ID6323481
Kegg IDC00157
ChemSpider ID24766671
FOODB IDFDB025193
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.