PC(14:1(9Z)/14:0) (YMDB01830)

Identification
YMDB IDYMDB01830
NamePC(14:1(9Z)/14:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(14:1(9Z)/14:0) 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(14:1(9Z)/14:0), in particular, consists of one chain of myristoleic acid at the C-1 position and one chain of myristic acid at the C-2 position. The myristoleic acid moiety is derived from milk fats, while the myristic acid moiety is derived from nutmeg and butter. 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
MOLSDFPDBSMILESInChI
Synonyms
  • 1-myristoleoyl-2-myristoyl-sn-glycero-3-phosphocholine
  • GPCho(14:1/14:0)
  • GPCho(14:1n5/14:0)
  • GPCho(14:1w5/14:0)
  • GPCho(28:1)
  • Lecithin
  • PC(14:1n5/14:0)
  • PC(14:1w5/14:0)
  • PC(28:1)
  • Phosphatidylcholine(14:1/14:0)
  • Phosphatidylcholine(14:1n5/14:0)
  • Phosphatidylcholine(14:1w5/14:0)
  • Phosphatidylcholine(28:1)
  • PC(14:1/14:0)
  • 1-Myristoleoyl-2-myristoyl-sn-glycero-3-phosphocholine
  • Phosphatidylcholine(28:1)
  • PC(28:1)
  • Phosphatidylcholine(14:1/14:0)
  • Lecithin
  • GPCho(14:1/14:0)
  • GPCho(28:1)
  • 1-(9Z-Tetradecenoyl)-2-tetradecanoyl-sn-glycero-3-phosphocholine
  • PC(14:1(9Z)/14:0)
CAS numberNot Available
WeightAverage: 675.9167
Monoisotopic: 675.483904733
InChI KeyXQPYHFHTTVXZKL-UUWRZZSWSA-N
InChIInChI=1S/C36H70NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-35(38)42-32-34(33-44-46(40,41)43-31-30-37(3,4)5)45-36(39)29-27-25-23-21-19-17-15-13-11-9-7-2/h12,14,34H,6-11,13,15-33H2,1-5H3/t34-/m1/s1
IUPAC Nametrimethyl(2-{[(2R)-3-[(9Z)-tetradec-9-enoyloxy]-2-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)azanium
Traditional IUPAC Namelecithin
Chemical FormulaC36H70NO8P
SMILESCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCC=CCCCC)COP([O-])(=O)OCC[N+](C)(C)C
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 Solubility4.2e-05 g/LALOGPS
logP4.46ALOGPS
logP5.97ChemAxon
logS-7.2ALOGPS
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 Count35ChemAxon
Refractivity198.58 m³·mol⁻¹ChemAxon
Polarizability81.11 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
0.052 ± 0.0026 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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01wk-9620553000-6d138f7e85953d4ece10JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002r-9270714000-47f0054fe0edaa46537fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0910-4590301000-ebe699aa039592c32fa0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00m0-9470211000-80d4d78c93d0334a7a10JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-0090018000-6387133285e85fdae2c9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-1191043000-e03586a7e76be6ff03a9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-4291000000-8bf9668085aafe8fe155JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000900-23efe47e180661e62928JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0030000900-931ce8d673e04b6f55f0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-0090000400-ed7612e2f02e25222e13JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000009000-7758c98a5dd6e0447643JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000009000-9b85e71817316dd08c1eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-0800983000-f6ef0e5f0a0444f23588JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000009000-db7c90fe63745586beabJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-0600009000-74e9482b89e7476b0d25JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lr-1900503000-115579516283be1e52deJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000009000-724887a31238f844cc5fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000009000-fcb13f9b85a7f37b5cb3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-0102902000-767a404c9335cd8210aaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000009000-559731194e19bf038640JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-0090308000-62495e9dcc45c3e0a3c5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3394000000-040e028d94985748b842JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID89588
HMDB IDHMDB07899
Pubchem Compound ID52922244
Kegg IDC00157
ChemSpider ID24766575
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available