Showing metabocard for PC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)) (BMDB0008108)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:51:01 UTC
Update Date2020-06-04 19:27:18 UTC
BMDB IDBMDB0008108
Secondary Accession Numbers
  • BMDB08108
Metabolite Identification
Common NamePC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))
DescriptionPC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)), also known as gpcho(36:5) or phosphatidylcholine(36:5), 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)/18:4(6Z,9Z,12Z,15Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)) can be biosynthesized from CDP-choline and DG(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)) and L-serine can be converted into choline and PS(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)); which is catalyzed by the enzyme phosphatidylserine synthase. In cattle, PC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
GPCho(36:5)HMDB
Phosphatidylcholine(36:5)HMDB
1-Oleoyl-2-stearidonoyl-sn-glycero-3-phosphocholineHMDB
LecithinHMDB
PC(36:5)HMDB
GPCho(18:1/18:4)HMDB
PC(18:1/18:4)HMDB
1-(9Z-Octadecenoyl)-2-(6Z,9Z,12Z,15Z-octadecatetraenoyl)-sn-glycero-3-phosphocholineHMDB
Phosphatidylcholine(18:1/18:4)HMDB
PC(18:1(9Z)/18:4(6Z,9Z,12Z,15Z))Lipid Annotator
Chemical FormulaC44H78NO8P
Average Molecular Weight780.0658
Monoisotopic Molecular Weight779.546504989
IUPAC Nametrimethyl(2-{[(2R)-3-[(9Z)-octadec-9-enoyloxy]-2-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]propyl phosphono]oxy}ethyl)azanium
Traditional Nametrimethyl(2-{[(2R)-3-[(9Z)-octadec-9-enoyloxy]-2-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]propyl phosphono]oxy}ethyl)azanium
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C44H78NO8P/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/h9,11,15,17,20-23,27,29,42H,6-8,10,12-14,16,18-19,24-26,28,30-41H2,1-5H3/b11-9-,17-15-,22-20-,23-21-,29-27-/t42-/m1/s1
InChI KeyVTBLOCMXAXXMCO-ITFWVWPTSA-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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.08ChemAxon
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 Count39ChemAxon
Refractivity239.85 m³·mol⁻¹ChemAxon
Polarizability92.92 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-9081151400-4112e28efed5d7ebecdcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0apu-4292020100-e62432fc6a072c9c81dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9085030100-3cbb1768bd491756a58dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01u0-0090000300-6ba917689087e9807531View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-0090001000-b81cef575e2f01905159View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01si-3090000000-340156d2ade5cf35c3a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000090-be732a4aa7f691f68131View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000190-37d5d9b145362a874a18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-0900369110-6f2badcde45eb44b003eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-11abb7219d74a5a60a04View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000900-8b887b2cddb30aa5f84aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0089-1900140300-a515e1107ea43be00829View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-d1fecbe733b4fab2e6fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0030000090-23cae743a073005be319View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03ji-0090000040-7d23db43f03230bd8138View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000900-06e9c04e0690d64ab8bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1090000100-1f752ffe5329cfb36251View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-3191000000-0b33529765919fdc9df5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000900-82395bc23558c5e73383View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000000900-d73ebce581a3424e67e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0200498400-ebfe0e64b9947db0b07aView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Milk
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified0.23 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.280 +/- 0.003 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.349 +/- 0.003 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.200 +/- 0.002 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.018 +/- 0.019 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008108
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24766770
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52922687
PDB IDNot Available
ChEBI ID89603
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.