Showing metabocard for PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)) (BMDB0008015)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:49:02 UTC
Update Date2020-06-04 19:27:17 UTC
BMDB IDBMDB0008015
Secondary Accession Numbers
  • BMDB08015
Metabolite Identification
Common NamePC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))
DescriptionPC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)), also known as 13.phosphatidylcholine(16:1n7/20:4n6) or gpcho(16:1/20:4), 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(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)) is considered to be a glycerophosphocholine lipid molecule. PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)) exists in all eukaryotes, ranging from yeast to humans. PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)) can be biosynthesized from CDP-choline and DG(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)) and L-serine can be converted into choline and PS(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)); which is catalyzed by the enzyme phosphatidylserine synthase. In cattle, PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)) pathway and phosphatidylethanolamine biosynthesis pe(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Palmitoleoyl-2-arachidonoyl-sn-glycero-3-phosphocholineChEBI
13.Phosphatidylcholine(16:1n7/20:4n6)ChEBI
GPCho(16:1/20:4)ChEBI
GPCho(16:1n7/20:4n6)ChEBI
GPCho(16:1W7/20:4W6)ChEBI
GPCho(36:5)ChEBI
PC(16:1/20:4)ChEBI
PC(16:1n7/20:4n6)ChEBI
PC(16:1W7/20:4W6)ChEBI
Phosphatidylcholine(16:1/20:4)ChEBI
Phosphatidylcholine(16:1W7/20:4W6)ChEBI
Phosphatidylcholine(36:5)HMDB
LecithinHMDB
PC(36:5)HMDB
1-(9Z-Hexadecenoyl)-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycero-3-phosphocholineHMDB
PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))Lipid Annotator
Chemical FormulaC44H78NO8P
Average Molecular Weight780.0658
Monoisotopic Molecular Weight779.546504989
IUPAC Name(2-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCC\C=C/CCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C44H78NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-25-27-29-31-33-35-37-44(47)53-42(41-52-54(48,49)51-39-38-45(3,4)5)40-50-43(46)36-34-32-30-28-26-24-19-17-15-13-11-9-7-2/h14,16-17,19-21,23,25,29,31,42H,6-13,15,18,22,24,26-28,30,32-41H2,1-5H3/b16-14-,19-17-,21-20-,25-23-,31-29-/t42-/m1/s1
InChI KeyDYDDZDMJSQYFGN-OIVUZXIWSA-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
logP5.58ALOGPS
logP8.08ChemAxon
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 Count39ChemAxon
Refractivity239.85 m³·mol⁻¹ChemAxon
Polarizability92.4 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, Positivesplash10-000i-8191231300-0653a286acdaa870d07cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3291010000-c65e741bad9673c66ac3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-7192011100-766a99b22c3e3b536c3fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ug0-0092000300-f86db0f76b9e3714547dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0090001000-a563a7058db3d642ea95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zg0-4092000000-4e1430acd2175e4d315cView 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-0011000090-657bdc19c312f171294eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0w29-0099000090-160e782e48f952383439View 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, Positivesplash10-014k-0900449110-fe0e3421d9ad9cbcb54aView 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, Positivesplash10-001i-1900230300-d99dd5310fb4160e5ef8View 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, Positivesplash10-0ue9-0200669400-dbafed5414ae6d5e1857View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000900-6ac0ce44c5d362b404abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-0053030900-45048af3aa1803a9c9cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-5391100000-15be4a0c5b1638caacacView 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 IDHMDB0008015
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025206
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24778771
PDB IDNot Available
ChEBI ID84816
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.

Enzymes

Enzyme Details
1. Phosphatidylserine synthase 1
General function:
Not Available
Specific function:
Catalyzes a base-exchange reaction in which the polar head group of phosphatidylethanolamine (PE) or phosphatidylcholine (PC) is replaced by L-serine. In membranes, PTDSS1 catalyzes mainly the conversion of phosphatidylcholine. Also converts, in vitro and to a lesser extent, phosphatidylethanolamine (By similarity).
Gene Name:
PTDSS1
Uniprot ID:
Q2KHY9
Molecular weight:
55416.0
Reactions
PC(16:1(9Z)/20:4(5Z,8Z,11Z,14Z)) + L-Serine → Choline + PS(16:1(9Z)/20:4(5Z,8Z,11Z,14Z))details