Showing metabocard for PC(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)) (BMDB0008660)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 17:26:24 UTC
Update Date2020-06-04 20:05:13 UTC
BMDB IDBMDB0008660
Secondary Accession Numbers
  • BMDB08660
Metabolite Identification
Common NamePC(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))
DescriptionPC(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)) 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)/16:1(9Z)), in particular, consists of one 4Z,7Z,10Z,13Z,16Z-docosapentaenoyl chain to the C-1 atom, and one 9Z-hexadecenoyl 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
1-Docosapentaenoyl-2-palmitoleoyl-sn-glycero-3-phosphocholineHMDB
1-Osbondoyl-2-palmitoleoyl-sn-glycero-3-phosphocholineHMDB
Gpcho(22:5/16:1)HMDB
Gpcho(22:5n6/16:1n7)HMDB
Gpcho(22:5W6/16:1W7)HMDB
Gpcho(38:6)HMDB
LecithinHMDB
PC Aa C38:6HMDB
PC(22:5/16:1)HMDB
PC(22:5n6/16:1n7)HMDB
PC(22:5W6/16:1W7)HMDB
PC(38:6)HMDB
Phosphatidylcholine(22:5/16:1)HMDB
Phosphatidylcholine(22:5n6/16:1n7)HMDB
Phosphatidylcholine(22:5W6/16:1W7)HMDB
Phosphatidylcholine(38:6)HMDB
1-(4Z,7Z,10Z,13Z,16Z-Docosapentaenoyl)-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholineHMDB
PC(22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z))Lipid Annotator
Chemical FormulaC46H80NO8P
Average Molecular Weight806.1031
Monoisotopic Molecular Weight805.562155053
IUPAC Name(2-{[(2R)-3-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-2-[(9Z)-hexadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-[(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoyloxy]-2-[(9Z)-hexadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
[H][C@@](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)OC(=O)CCCCCCC\C=C/CCCCCC
InChI Identifier
InChI=1S/C46H80NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-27-28-30-32-34-36-38-45(48)52-42-44(43-54-56(50,51)53-41-40-47(3,4)5)55-46(49)39-37-35-33-31-29-26-19-17-15-13-11-9-7-2/h14,16-17,19-21,23-24,27-28,32,34,44H,6-13,15,18,22,25-26,29-31,33,35-43H2,1-5H3/b16-14-,19-17-,21-20-,24-23-,28-27-,34-32-/t44-/m1/s1
InChI KeyZQVQZWAPLCJLRX-SCEKUSSYSA-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
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
logP5.78ALOGPS
logP8.61ChemAxon
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 Count40ChemAxon
Refractivity250.17 m³·mol⁻¹ChemAxon
Polarizability94.58 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-9164131220-aef096f350eb05cfa344View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-4394011100-d7e99ef61dc3eea9d1d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9166003100-065923efae7a562cf053View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0w4i-0049000030-0c8e1c7468817722ee2eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-0039000100-71162af6f01c296af8c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004r-6096100000-03d9ff2d13a136f289e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000090-6dad79f01b1173c5421fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0057005390-4647d83d0b76ce8fd01dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-117i-6297500000-37821a066f8f4f3c77d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-1e78e28c2730b5262b1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000190-f42482894aa2a9df4b6dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0200669220-b836efc9966588254403View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000090-16b357af2387839179b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0011000090-db5073fd978f70656a5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ui6-0099000090-5ee930ee2a2d2b44392bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000090-8b00eebc929d9a9097dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000000190-71d714a518c51ee5a089View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0900369110-6ceca10b562388b251f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000090-489803391fb15e1d23f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-0600000090-e0c7549473f8627cae46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0089-1900221210-f7cad82e27c9d63fc8e8View 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 Quantified1 +/- 0.3 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
LiverDetected and Quantified6 +/- 3 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Longissimus Thoracis MuscleDetected and Quantified0.5 +/- 0.1 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Ruminal FluidDetected and Quantified0.06 +/- 0.04 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Ruminal FluidDetected and Quantified0.020 +/- 0.014 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Semimembranosus MuscleDetected and Quantified0.6 +/- 0.2 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
TestisDetected and Quantified21 +/- 5 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008660
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025850
KNApSAcK IDNot Available
Chemspider ID24767321
KEGG Compound IDC00157
BioCyc ID PHOSPHATIDYLCHOLINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53479283
PDB IDNot Available
ChEBI ID88422
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available