Showing metabocard for PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (BMDB0008123)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 17:14:12 UTC
Update Date2020-05-21 16:28:20 UTC
BMDB IDBMDB0008123
Secondary Accession Numbers
  • BMDB08123
Metabolite Identification
Common NamePC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
DescriptionPC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), also known as PC(18:1/22:6) or 1-oleoyl-2-docosahexaenoyl-GPC, 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)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be biosynthesized from CDP-choline and DG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) and L-serine can be converted into choline and PS(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway and phosphatidylethanolamine biosynthesis pe(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(9Z-Octadecenoyl)-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphocholineChEBI
1-Oleoyl-2-docosahexaenoyl-GPCChEBI
1-Oleoyl-2-docosahexaenoyl-GPC (18:1/22:6)ChEBI
1-Oleoyl-2-docosahexaenoyl-sn-glycero-3-phosphocholineChEBI
GPC(18:1/22:6)ChEBI
GPCho(18:1/22:6)ChEBI
GPCho(18:1n9/22:6n3)ChEBI
GPCho(18:1W9/22:6W3)ChEBI
PC(18:1/22:6)ChEBI
PC(18:1n9/22:6n3)ChEBI
PC(18:1W9/22:6W3)ChEBI
Phosphatidylcholine(18:1/22:6)ChEBI
Phosphatidylcholine(18:1n9/22:6n3)ChEBI
Phosphatidylcholine(18:1W9/22:6W3)ChEBI
1-Oleoyl-2-docosahexaenoylglycero-3-phosphorylcholineHMDB
1-ODHPCHMDB
1-Oleoyl-2-dha-PCHMDB
1-Oleoyl-2-docosahexaenoyl phosphatidylcholineHMDB
GPCho(40:7)HMDB
LecithinHMDB
Phosphatidylcholine(40:7)HMDB
PC(40:7)HMDB
PC(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))Lipid Annotator
Chemical FormulaC48H82NO8P
Average Molecular Weight832.1403
Monoisotopic Molecular Weight831.577805117
IUPAC Name(2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C48H82NO8P/c1-6-8-10-12-14-16-18-20-22-23-24-25-27-29-31-33-35-37-39-41-48(51)57-46(45-56-58(52,53)55-43-42-49(3,4)5)44-54-47(50)40-38-36-34-32-30-28-26-21-19-17-15-13-11-9-7-2/h8,10,14,16,20-22,24-26,29,31,35,37,46H,6-7,9,11-13,15,17-19,23,27-28,30,32-34,36,38-45H2,1-5H3/b10-8-,16-14-,22-20-,25-24-,26-21-,31-29-,37-35-/t46-/m1/s1
InChI KeyFPEVDFOXMCHLKL-KFDYCXSYSA-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
logP5.9ALOGPS
logP9.14ChemAxon
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 Count41ChemAxon
Refractivity260.49 m³·mol⁻¹ChemAxon
Polarizability98.74 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, Positivesplash10-001i-0000000090-79f227f2d9029f28e7e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000090-924f091d218719cd1b75View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-1900041120-9baee8374a0c3e7329f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0093000030-ec8656723a30a525c583View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-0091000100-5783b610f5d7b4fd7e30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06w9-5095000000-a12c963b60b3d03fa275View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000000090-9ba117d1c0de1c2e67a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0600000090-d0b4cd4d5b1d3c3b81bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ff0-1900041120-ef5e60e7b652c633f0ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000090-b0b8959ba582c76807b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0011000090-b8190d8ba7ea3bb4e466View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ai-0099000090-8374d15f57f1ded56758View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000090-620340c637035e66e687View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000190-3bb76294110b3cbe4d52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dk-0900179110-bdfdcea3af515e6884d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000090-9663725765fd23c75bffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0044004490-1002bc162cfeff2d6df3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-3192000000-0505b81ab7820b9f17d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000090-28e9f69759c65edf3511View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000000190-f4871623ad0b081e303cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0200498220-6d6cbbe2f4f218dac20aView 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 IDHMDB0008123
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025313
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24778955
PDB IDNot Available
ChEBI ID84814
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) + L-Serine → Choline + PS(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))details