Showing metabocard for LysoPC(22:4(7Z,10Z,13Z,16Z)) (BMDB0010401)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:05:53 UTC
Update Date2020-05-11 19:11:22 UTC
BMDB IDBMDB0010401
Secondary Accession Numbers
  • BMDB10401
Metabolite Identification
Common NameLysoPC(22:4(7Z,10Z,13Z,16Z))
DescriptionLysoPC(22:4(7Z,10Z,13Z,16Z)/0:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. LysoPC(22:4(7Z,10Z,13Z,16Z)/0:0), in particular, consists of one 7Z,10Z,13Z,16Z-docosatetraenoyl chain. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(20:3(5Z,8Z,11Z)), in particular, consists of one chain of mead acid at the C-1 position. The mead acid moiety is derived from fish oils, liver and kidney. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(7Z,10Z,13Z,16Z-Docosatetraenoyl)-glycero-3-phosphocholineChEBI
1-Adrenoyl-glycero-3-phosphocholineChEBI
1-Adrenoyl-GPCChEBI
1-Adrenoyl-GPC (22:4)ChEBI
1-Adrenoyl-sn-glycero-3-phosphocholineChEBI
GPC(22:4)ChEBI
GPC(22:4/0:0)ChEBI
LPC(22:4(7Z,10Z,13Z,16Z)/0:0)ChEBI
LPC(22:4)ChEBI
LPC(22:4/0:0)ChEBI
LPC(22:4n6/0:0)ChEBI
LPC(22:4W6/0:0)ChEBI
LyPC(22:4)ChEBI
LyPC(22:4/0:0)ChEBI
LyPC(22:4n6/0:0)ChEBI
LyPC(22:4W6/0:0)ChEBI
LysoPC(22:4)ChEBI
LysoPC(22:4/0:0)ChEBI
LysoPC(22:4n6/0:0)ChEBI
LysoPC(22:4W6/0:0)ChEBI
Lysophosphatidylcholine(22:4)ChEBI
Lysophosphatidylcholine(22:4/0:0)ChEBI
Lysophosphatidylcholine(22:4n6/0:0)ChEBI
Lysophosphatidylcholine(22:4W6/0:0)ChEBI
PC(22:4(7Z,10Z,13Z,16Z)/0:0)ChEBI
LysoPC(22:4(7Z,10Z,13Z,16Z))HMDB
1-AdrenoylglycerophosphocholineHMDB
Chemical FormulaC30H54NO7P
Average Molecular Weight571.726
Monoisotopic Molecular Weight571.363789599
IUPAC Name(2-{[(2R)-3-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-[(7Z,10Z,13Z,16Z)-docosa-7,10,13,16-tetraenoyloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(=O)OC[C@](O)([H])COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C30H54NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-30(33)36-27-29(32)28-38-39(34,35)37-26-25-31(2,3)4/h9-10,12-13,15-16,18-19,29,32H,5-8,11,14,17,20-28H2,1-4H3/b10-9-,13-12-,16-15-,19-18-/t29-/m1/s1
InChI KeyZOJBSSVHFSBHMP-JJJSWPRASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-acyl-sn-glycero-3-phosphocholines
Alternative Parents
Substituents
  • 1-acyl-sn-glycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic salt
  • Amine
  • 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
logP3.03ALOGPS
logP2.41ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area105.12 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity174.35 m³·mol⁻¹ChemAxon
Polarizability65.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-024u-9432012000-c1ea4b26504c04725c4eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("LysoPC(22:4(7Z,10Z,13Z,16Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000090000-9c2f07cddacd37b638c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0190-0001090000-9cf5b92d1aeab3b5a936View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0frj-0309040000-11f90b2843a2cd4891b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000090000-01fe2ec9d7eb15d6b4aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-0000090000-48a51bbd4b5e4e7b0f4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gw0-1601790000-1947090a55dc8278ef51View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0003090000-359626919977f632df6dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1009010000-7718609651953c03c652View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1009000000-78b6d8058c705b640de4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0000090000-7282f84bb93138814d4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-0900060000-31c3e53929caab2772acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-0910040000-b41159c5d6a65ee1049fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000039000-aa4234fa1ba784c6332fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-0009016000-261cd04940c1d0331f90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0039011000-c029b676a207f32d2a6cView 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 IDHMDB0010401
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027552
KNApSAcK IDNot Available
Chemspider ID24766536
KEGG Compound IDC04230
BioCyc ID PHOSPHATIDYLCHOLINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52924039
PDB IDNot Available
ChEBI ID133657
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available