1-18:1-2-18:2-phosphatidylcholine (CHEM041808)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:42:28 UTC
Update Date2016-11-09 01:22:32 UTC
Accession NumberCHEM041808
Identification
Common Name1-18:1-2-18:2-phosphatidylcholine
ClassSmall Molecule
DescriptionPC(18:1(9Z)/18:2(9Z,12Z)), also known as PC(18:1/18:2) or PC(18:1omega9/18:2omega6), 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. Thus, PC(18:1(9Z)/18:2(9Z,12Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:1(9Z)/18:2(9Z,12Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:1(9Z)/18:2(9Z,12Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:1(9Z)/18:2(9Z,12Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:1(9Z)/18:2(9Z,12Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:1(9Z)/18:2(9Z,12Z)); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:1(9Z)/18:2(9Z,12Z)) can be biosynthesized from CDP-choline and DG(18:1(9Z)/18:2(9Z,12Z)/0:0); which is mediated by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:1(9Z)/18:2(9Z,12Z)) and L-serine can be converted into choline and PS(18:1(9Z)/18:2(9Z,12Z)) through its interaction with the enzyme phosphatidylserine synthase. In cattle, PC(18:1(9Z)/18:2(9Z,12Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:1(9Z)/18:2(9Z,12Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:1(9Z)/18:2(9Z,12Z)) pathway.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(9Z)-Octadecaenoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholineChEBI
1-(9Z-Octadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholineChEBI
1-C18:1(Omega-9)-2-C18:2(omega-6)-phosphatidylcholineChEBI
1-Oleoyl-2-linoleoyl-GPCChEBI
1-Oleoyl-2-linoleoyl-GPC (18:1/18:2)ChEBI
GPC(18:1/18:2)ChEBI
PC(18:1/18:2)ChEBI
PC(18:1Omega9/18:2omega6)ChEBI
PC(36:3)ChEBI
Phosphatidylcholine(18:1/18:2)ChEBI
Phosphatidylcholine(18:1omega9/18:2omega6)ChEBI
Phosphatidylcholine(36:3)ChEBI
1-Oleoyl-2-linoleoyl-sn-glycero-3-phosphocholineHMDB
GPCho(36:3)HMDB
GPCho(18:1/18:2)HMDB
LecithinHMDB
1-Oleoyl-2-linoleoyl lecithinHMDB
1-Oleoyl-2-linoleoyl phosphatidylcholineHMDB
1-Oleoyl-2-linoleoyl-sn-glycero-phosphatidylcholineHMDB
GPC(18:1(9Z)/18:2(9Z,12Z))HMDB
GPC(18:1n9/18:2n6)HMDB
GPC(18:1W9/18:2W6)HMDB
GPC(36:3)HMDB
GPCho(18:1(9Z)/18:2(9Z,12Z))HMDB
GPCho(18:1n9/18:2n6)HMDB
GPCho(18:1W9/18:2W6)HMDB
L-(+)-alpha-(Alpha'-oleoyl-beta-linoleoyl)glycerylphosphorylcholineHMDB
L-(+)-Α-(α'-oleoyl-β-linoleoyl)glycerylphosphorylcholineHMDB
L-(+)-Α-(α’-oleoyl-β-linoleoyl)glycerylphosphorylcholineHMDB
PC(18:1n9/18:2n6)HMDB
PC(18:1W9/18:2W6)HMDB
Phosphatidylcholine(18:1(9Z)/18:2(9Z,12Z))HMDB
Phosphatidylcholine(18:1n9/18:2n6)HMDB
Phosphatidylcholine(18:1W9/18:2W6)HMDB
PC(18:1(9Z)/18:2(9Z,12Z))Lipid Annotator, ChEBI
Chemical FormulaC44H82NO8P
Average Molecular Mass784.098 g/mol
Monoisotopic Mass783.578 g/mol
CAS Registry NumberNot Available
IUPAC Nametrimethyl(2-{[(2R)-3-[(9Z)-octadec-9-enoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)azanium
Traditional Nametrimethyl(2-{[(2R)-3-[(9Z)-octadec-9-enoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)azanium
SMILESCCCCCCCC\C=C/CCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI IdentifierInChI=1S/C44H82NO8P/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/h15,17,20-23,42H,6-14,16,18-19,24-41H2,1-5H3/b17-15-,22-20-,23-21-/t42-/m1/s1
InChI KeyGDWULUGDXGHJIJ-VJHNMZKJSA-N
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.6e-05 g/LALOGPS
logP5.74ALOGPS
logP8.81ChemAxon
logS-7.5ALOGPS
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 Count41ChemAxon
Refractivity237.62 m³·mol⁻¹ChemAxon
Polarizability93.97 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000400-673c4b41bf0baa3179b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-0090001000-a565c7b509c80f248611Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01si-3090100000-d9f0aaac3713bc0352beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000900-f313232611c4c0c71d38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090020800-2f1b9f57c7195f8960efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2190100000-5ec20bd547c21812e0b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000090-02472e506be910245a7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0030000090-3c7d05d682b05a083951Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ai-0090000040-4c2666c7619b17b07955Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fs9-9051052400-a89d585222552400de65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01c9-5393033100-37ce295c82fbf076874fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-9056031100-7f29f68a8e68350100baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-016fbc06bd6c36a12e4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000900-7ba4362bb833d26b28b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ff0-1900041300-a8960ec50ee7c8790e73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000900-f44acebd42271f9d37feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000900-d39b20e156e47b15fe77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0200498400-c711e23d2ffb1410e86bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000090-1db30625399fdea6b457Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000190-671ed31d83ec847480a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dk-0900369110-e9eb218755dd4edd13b3Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0008105
FooDB IDFDB030211
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID74670
PubChem Compound ID24778939
Kegg Compound IDNot Available
YMDB IDYMDB01937
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)
2. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.