PC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) (YMDB02007)

Identification
YMDB IDYMDB02007
NamePC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)) 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(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z)), in particular, consists of two chains of a-linolenic acid at the C-1 and C-2 positions. The a-linolenic acid moieties are derived from seed oils, especially canola and soybean 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
MOLSDFPDBSMILESInChI
Synonyms
  • GPCho(18:3/18:3)
  • GPCho(18:3n3/18:3n3)
  • GPCho(18:3w3/18:3w3)
  • GPCho(36:6)
  • Lecithin
  • PC(18:3/18:3)
  • PC(18:3n3/18:3n3)
  • PC(18:3w3/18:3w3)
  • PC(36:6)
  • Phosphatidylcholine(18:3/18:3)
  • Phosphatidylcholine(18:3n3/18:3n3)
  • Phosphatidylcholine(18:3w3/18:3w3)
  • Phosphatidylcholine(36:6)
  • 1,2-dia-linolenoyl-rac-glycero-3-phosphocholine
  • GPCho(18:3/18:3)
  • GPCho(18:3n3/18:3n3)
  • GPCho(18:3W3/18:3W3)
  • PC(18:3/18:3)
  • PC(18:3n3/18:3n3)
  • PC(18:3W3/18:3W3)
  • Phosphatidylcholine(18:3/18:3)
  • Phosphatidylcholine(18:3n3/18:3n3)
  • Phosphatidylcholine(18:3W3/18:3W3)
  • Phosphatidylcholine(36:6)
  • GPCho(36:6)
  • Lecithin
  • PC(36:6)
  • 1,2-Di(9Z,12Z,15Z-octadeatrienoyl)-rac-glycero-3-phosphocholine
  • 1,2-Dilinolenoyl-sn-glycero-3-phosphatidylcholine
  • 1,2-Dilinolenoylphosphatidylcholine
  • DLPC (Linolenoyl) lipid
  • PC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))
  • 1,2-Dialpha-linolenoyl-GPC
  • 1,2-Dialpha-linolenoyl-sn-glycero-3-phosphocholine
  • 1,2-Dialpha-linolenoyl-sn-glycero-phosphatidylcholine
  • 1,2-Dilinolenoyl-GPC
  • 1,2-Dilinolenoyl-sn-glycero-3-phosphocholine
  • Dilinolenoyl lecithin
  • Dilinolenoylphosphatidylcholine
  • GPC(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))
  • GPC(18:3/18:3)
  • GPC(18:3n3/18:3n3)
  • GPC(18:3w3/18:3w3)
  • GPC(36:6)
  • GPCho(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))
  • L-Dilinolenoyl lecithin
  • L-alpha-Di(cis,cis,cis-9,12,15-octadecatrienoyl) lecithin
  • L-alpha-Dilinolenoyl phosphatidylcholine
  • L-α-Di(cis,cis,cis-9,12,15-octadecatrienoyl) lecithin
  • L-α-Dilinolenoyl phosphatidylcholine
  • Phosphatidylcholine(18:3(9Z,12Z,15Z)/18:3(9Z,12Z,15Z))
CAS numberNot Available
WeightAverage: 778.0499
Monoisotopic: 777.530854925
InChI KeyXXKFQTJOJZELMD-HUESYALOSA-N
InChIInChI=1S/C44H76NO8P/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/h8-11,14-17,20-23,42H,6-7,12-13,18-19,24-41H2,1-5H3/t42-/m1/s1
IUPAC Name(2-{[(2R)-2,3-bis[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[(2R)-2,3-bis[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Chemical FormulaC44H76NO8P
SMILESCCC=CCC=CCC=CCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCC=CCC=CCC
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 Solubility3.6e-05 g/LALOGPS
logP5.34ALOGPS
logP7.72ChemAxon
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
Refractivity240.97 m³·mol⁻¹ChemAxon
Polarizability91.38 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
0.021 ± 0.00105 µM YEB media with 0.5 mM glucoseaerobicBrewer's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - IT 40V, negativesplash10-03di-0030020930-b04a9be78829ff3219a0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - IT 30V, positivesplash10-003r-0900010500-c970039605c9f604c652JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 23V, positivesplash10-004i-0000000900-f837314e003c3113eb1fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 35V, positivesplash10-003r-0900000600-92f5630d60c09ddc321bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 48V, positivesplash10-001i-0900000000-9f98f26880b83576e000JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 59V, positivesplash10-001i-0900000000-4974bb5a3deda8855a56JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 71V, positivesplash10-001i-0900000000-7d7f52656eb8e463d8d7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 83V, positivesplash10-001i-1900000000-1b646130ad373ee1f327JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 96V, positivesplash10-001i-3900000000-3b5d29ad855bb63e6937JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 108V, positivesplash10-001i-4900000000-b7301a9f30c5899d2693JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 119V, positivesplash10-001r-6900000000-83408e36a7976e7bf701JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 144V, positivesplash10-003i-9800000000-6ba7dbc7bfc88b830d44JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 180V, positivesplash10-002r-9500000000-cc6f65c360783bb9a2a2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 217V, positivesplash10-002s-9300000000-edbc43f25aa0849d3e17JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 265V, positivesplash10-006t-9100000000-35bfcabf3f76210dc62eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 314V, positivesplash10-0002-9000000000-cde5ee66653888ffbd24JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 387V, positivesplash10-0002-9000000000-f8598eeba460ada3ca58JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01p9-9051061400-057fe0081044e2f48e7cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03yr-6395052200-cdf2814236901dca5853JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00li-9057043100-252c59a1d38b47e6b1ecJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000400-09785e8202c3360f75f8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0090001000-0668f1ba3bed11b37ad8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-4090100000-69fe58cd77008d99959eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000900-e158c1e70dedba30b57eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-0600000900-259bce635b325b3b4835JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID86161
HMDB IDHMDB08206
Pubchem Compound ID24778990
Kegg IDC00157
ChemSpider ID24766868
FOODB IDFDB030240
Wikipedia IDNot Available
BioCyc IDNot Available