Showing metabocard for PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (BMDB0008017)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:49:05 UTC
Update Date2020-06-04 19:43:22 UTC
BMDB IDBMDB0008017
Secondary Accession Numbers
  • BMDB08017
Metabolite Identification
Common NamePC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))
DescriptionPC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)), also known as PC(16:1/20:5) or pc(16:1(9z)/20:5(5z,8z,11z,14z,17z)), 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)/20:5(5Z,8Z,11Z,14Z,17Z)) is considered to be a glycerophosphocholine lipid molecule. PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)) exists in all eukaryotes, ranging from yeast to humans. PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)) can be biosynthesized from CDP-choline and DG(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)) and L-serine can be converted into choline and PS(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)) through the action of the enzyme phosphatidylserine synthase. In cattle, PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)) pathway and phosphatidylethanolamine biosynthesis pe(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PC(16:1/20:5)HMDB
GPCho(16:1/20:5)HMDB
GPCho(36:6)HMDB
1-Palmitoleoyl-2-eicosapentaenoyl-sn-glycero-3-phosphocholineHMDB
LecithinHMDB
PC(36:6)HMDB
Phosphatidylcholine(16:1/20:5)HMDB
1-(9Z-Hexadecenoyl)-2-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phosphocholineHMDB
Phosphatidylcholine(36:6)HMDB
PC(16:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))Lipid Annotator
Chemical FormulaC44H76NO8P
Average Molecular Weight778.0499
Monoisotopic Molecular Weight777.530854925
IUPAC Name(2-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C44H76NO8P/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/h8,10,14,16-17,19-21,23,25,29,31,42H,6-7,9,11-13,15,18,22,24,26-28,30,32-41H2,1-5H3/b10-8-,16-14-,19-17-,21-20-,25-23-,31-29-/t42-/m1/s1
InChI KeyIITWSVMUNFGFQI-MMWBFVNXSA-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
logP5.4ALOGPS
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
Polarizability91.28 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, Positivesplash10-004i-0000000900-d952f38d42ad6ddf6054View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-0600000900-c704be0a3ccac58b5732View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900230300-51b10f425373e7a76e5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ug0-0092000300-281d6b4ee7b6b5db2a03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090001000-4afb40e0fd8710fdab4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-4092000000-712e6ecc05b5f1067029View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000900-41c33084af9f783c847dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000000900-dd151cc7bd543b751825View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-0200669400-8bd41403b444f4938a28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000090-e97180150486da753e49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000190-cd910875d8659ad53678View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-0900449110-84a47156b3f0d4881387View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000900-5a1f7e5d648203ccaa08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0053030900-f8a6a6b51561524fa0f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-3291000000-9f9e15b7ce5aa3f92896View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000900-e158c1e70dedba30b57eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-0600000900-259bce635b325b3b4835View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900230300-bae344dcea43b8ff0b76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000000090-87e491c712a61c58fe72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0011000090-00ac5bf7d774a451f19dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0w29-0099000090-341e85ab53fc2ceadb5bView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Blood
  • Liver
  • Longissimus Thoracis Muscle
  • Ruminal Fluid
  • Semimembranosus Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
BloodDetected and Quantified0.7 +/- 0.2 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
LiverDetected and Quantified3 +/- 1 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Longissimus Thoracis MuscleDetected and Quantified0.3 +/- 0.1 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Ruminal FluidDetected and Quantified0.017 +/- 0.007 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Semimembranosus MuscleDetected and Quantified0.3 +/- 0.1 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
TestisDetected and Quantified0.4 +/- 0.1 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008017
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025208
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52922465
PDB IDNot Available
ChEBI ID89739
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available