Showing metabocard for PC(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) (BMDB0008149)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:14:50 UTC
Update Date2020-05-11 18:41:49 UTC
BMDB IDBMDB0008149
Secondary Accession Numbers
  • BMDB08149
Metabolite Identification
Common NamePC(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))
DescriptionPC(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)), also known as pc(18:2(9z,12z)/20:5(5z,8z,11z,14z,17z)) or pc(18:2(9z,12z)/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(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) can be biosynthesized from CDP-choline and DG(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) and L-serine can be converted into choline and PS(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) through its interaction with the enzyme phosphatidylserine synthase. In cattle, PC(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-linoleoyl-2-eicosapentaenoyl-sn-glycero-3-phosphocholineLipid Annotator, HMDB
GPCho(38:7)Lipid Annotator, HMDB
GPCho(18:2/20:5)Lipid Annotator, HMDB
Phosphatidylcholine(18:2/20:5)Lipid Annotator, HMDB
LecithinLipid Annotator, HMDB
Phosphatidylcholine(38:7)Lipid Annotator, HMDB
PC(18:2/20:5)Lipid Annotator, HMDB
PC(18:2(9Z,12Z)/20:5(5Z,8Z,11Z,14Z,17Z))Lipid Annotator
1-(9Z,12Z-octadecadienoyl)-2-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-phosphocholineLipid Annotator, HMDB
PC(38:7)Lipid Annotator, HMDB
Chemical FormulaC46H78NO8P
Average Molecular Weight804.0872
Monoisotopic Molecular Weight803.546504989
IUPAC Name(2-{[(2R)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\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/C\C=C/CC
InChI Identifier
InChI=1S/C46H78NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h8,10,14-17,20-22,24-25,27,31,33,44H,6-7,9,11-13,18-19,23,26,28-30,32,34-43H2,1-5H3/b10-8-,16-14-,17-15-,22-20-,24-21-,27-25-,33-31-/t44-/m1/s1
InChI KeyHRBNRYBXXRPMKP-QNDMKCBJSA-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
StatusExpected but not 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
logP5.52ALOGPS
logP8.25ChemAxon
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
Refractivity251.29 m³·mol⁻¹ChemAxon
Polarizability94.31 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, Positivesplash10-0udi-0000000090-db1455bde15546a91862View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0600000090-0adb83407e5859907221View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0089-1900041210-4119e47271b997b3e3cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000090-5728bb94da13a2a32b27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0600000090-f0a6ccb585b932e5c180View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0089-1900041210-fa6bae18bed9832e0de5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000090-6a6081c2784b60e92a31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0064005390-6ede99dbf37ece079e49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3191000000-2d1b48bbdb85576eb14cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000090-2938204409884798f461View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0011000090-d091ea60f99f4e31cec4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uii-0099000090-b84cabb8e71c8cd2f283View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-b39f0b29e79ad86fe71dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000190-e38f77ea0add8862dc86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0200498220-c2b7d031a6104a38f31fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000090-9767e8c77824f3458c02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000190-2806d1647d91bef91a92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0008-0900369110-8f737e121a034abb1375View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008149
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24766811
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52922747
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available