Showing metabocard for PC(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)) (BMDB0008664)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:26:29 UTC
Update Date2020-05-11 18:48:57 UTC
BMDB IDBMDB0008664
Secondary Accession Numbers
  • BMDB08664
Metabolite Identification
Common NamePC(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))
DescriptionPC(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)) is a phosphatidylchloline (PC). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylcholines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PC(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)), in particular, consists of one 4Z,7Z,10Z,13Z,16Z-docosapentaenoyl chain to the C-1 atom, and one 9Z,12Z-octadecadienoyl to the C-2 atom. In E. coli, PCs can be found in the integral component of the cell outer membrane. They are hydrolyzed by Phospholipases to a 2-acylglycerophosphocholine and a carboxylate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Phosphatidylcholine(40:7)Lipid Annotator, HMDB
GPCho(40:7)Lipid Annotator, HMDB
GPCho(22:5/18:2)Lipid Annotator, HMDB
LecithinLipid Annotator, HMDB
1-osbondoyl-2-linoleoyl-sn-glycero-3-phosphocholineLipid Annotator, HMDB
PC(22:5/18:2)Lipid Annotator, HMDB
PC(40:7)Lipid Annotator, HMDB
PC(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z))Lipid Annotator
1-(4Z,7Z,10Z,13Z,16Z-docosapentaenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholineLipid Annotator, HMDB
Phosphatidylcholine(22:5/18:2)Lipid Annotator, HMDB
1-Docosapentaenoyl-2-linoleoyl-sn-glycero-3-phosphocholineHMDB
gpcho(22:5n6/18:2n6)HMDB
gpcho(22:5W6/18:2W6)HMDB
PC(22:5n6/18:2n6)HMDB
PC(22:5W6/18:2W6)HMDB
Phosphatidylcholine(22:5n6/18:2n6)HMDB
Phosphatidylcholine(22:5W6/18:2W6)HMDB
Chemical FormulaC48H82NO8P
Average Molecular Weight832.1403
Monoisotopic Molecular Weight831.577805117
IUPAC Name(2-{[(2R)-3-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-2-[(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)O[C@]([H])(COC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C48H82NO8P/c1-6-8-10-12-14-16-18-20-22-23-24-25-27-28-30-32-34-36-38-40-47(50)54-44-46(45-56-58(52,53)55-43-42-49(3,4)5)57-48(51)41-39-37-35-33-31-29-26-21-19-17-15-13-11-9-7-2/h14-17,20-22,24-26,28,30,34,36,46H,6-13,18-19,23,27,29,31-33,35,37-45H2,1-5H3/b16-14-,17-15-,22-20-,25-24-,26-21-,30-28-,36-34-/t46-/m1/s1
InChI KeyQSTSWBKMHLOFSW-GBKOJJKOSA-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 DescriptorsNot Available
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
logP5.87ALOGPS
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
Polarizability97.75 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, Positivesplash10-0ff0-1900041120-19449a231f22abe1036fView 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-0011000090-11dbef59c4fba2d26abdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0099000090-caa5201357d17a2c760bView 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, Positivesplash10-00dj-0900179110-92028be4bb11e9bacc2fView 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-0047005490-1843324d76268bb57ad0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6289500100-90e81743f37c53ac241cView 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, Positivesplash10-0a6r-0200498220-231c02852a14826b9863View 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-f8dc216873de316881dbView 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 IDHMDB0008664
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24767325
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53479291
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available