You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB02265
NamePC(o-16:1(9Z)/20:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(o-16:1(9Z)/20:0) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(o-16:1(9Z)/20:0), in particular, consists of one chain of Palmitoleyl alcohol at the C-1 position and one chain of arachidic acid at the C-2 position. The Palmitoleyl alcohol moiety is derived from whale oil, while the arachidic acid moiety is derived from peanut oil. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.
Structure
Thumb
Synonyms
  • 1-Palmitoleyl-2-arachidonyl-sn-glycero-3-phosphocholine
  • GPCho(16:1/20:0)
  • GPCho(16:1n7/20:0)
  • GPCho(16:1w7/20:0)
  • Lecithin
  • PC(16:1/20:0)
  • PC(16:1n7/20:0)
  • PC(16:1w7/20:0)
  • PC(36:1)
  • Phosphatidylcholine(16:1/20:0)
  • Phosphatidylcholine(16:1n7/20:0)
  • Phosphatidylcholine(16:1w7/20:0)
  • Phosphatidylcholine(36:1)
  • GPCho(36:1)
CAS numberNot Available
WeightAverage: 774.1458
Monoisotopic: 773.629840687
InChI KeyNEMVGIRAGVGOLH-UHFFFAOYSA-N
InChIInChI=1S/C44H88NO7P/c1-6-8-10-12-14-16-18-20-22-23-24-25-27-29-31-33-35-37-44(46)52-43(42-51-53(47,48)50-40-38-45(3,4)5)41-49-39-36-34-32-30-28-26-21-19-17-15-13-11-9-7-2/h17,19,43H,6-16,18,20-42H2,1-5H3
IUPAC Name(2-{[3-(hexadec-9-en-1-yloxy)-2-(icosanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[3-(hexadec-9-en-1-yloxy)-2-(icosanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Chemical FormulaC44H88NO7P
SMILESCCCCCCCCCCCCCCCCCCCC(=O)OC(COCCCCCCCCC=CCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-alkyl,2-acylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-alkyl,2-acylglycero-3-phosphocholines
Alternative Parents
Substituents
  • 1-alkyl,2-acylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Glycerol ether
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.0e-05 g/LALOGPS
logP6.21ALOGPS
logP9.91ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area94.12 ŲChemAxon
Rotatable Bond Count43ChemAxon
Refractivity235.63 m³·mol⁻¹ChemAxon
Polarizability98.85 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 PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
0.087 ± 0.00435 µM YEB media with 0.5 mM glucoseaerobicBrewer's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
SpectraNot Available
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB13414
Pubchem Compound ID76043905
Kegg IDNot Available
ChemSpider ID24822863
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available