Showing metabocard for LysoPC(20:2(11Z,14Z)/0:0) (BMDB0109690)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2020-05-06 19:38:42 UTC
Update Date2020-05-07 14:45:01 UTC
BMDB IDBMDB0109690
Secondary Accession NumbersNone
Metabolite Identification
Common NameLysoPC(20:2(11Z,14Z)/0:0)
DescriptionLysoPC(20:2(11Z,14Z)/0:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. LysoPC(20:2(11Z,14Z)/0:0), in particular, consists of one 11Z,14Z-eicosadienoyl 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-[(11Z,14Z)]-Eicosadienoyl-sn-glycero-3-phosphocholineChEBI
1-Dihomo-linoleoyl-GPCChEBI
1-Dihomo-linoleoyl-GPC (20:2)ChEBI
1-EicosadienoylglycerophosphocholineChEBI
GPC(20:2)ChEBI
GPC(20:2/0:0)ChEBI
LPC(20:2)ChEBI
LPC(20:2/0:0)ChEBI
LPC(20:2n6/0:0)ChEBI
LPC(20:2W6/0:0)ChEBI
LyPC(20:2)ChEBI
LyPC(20:2/0:0)ChEBI
LyPC(20:2n6/0:0)ChEBI
LyPC(20:2W6/0:0)ChEBI
LysoPC(20:2(11Z,14Z))ChEBI
LysoPC(20:2)ChEBI
LysoPC(20:2/0:0)ChEBI
LysoPC(20:2n6/0:0)ChEBI
LysoPC(20:2W6/0:0)ChEBI
Lysophosphatidylcholine(20:2)ChEBI
Lysophosphatidylcholine(20:2/0:0)ChEBI
Lysophosphatidylcholine(20:2n6/0:0)ChEBI
Lysophosphatidylcholine(20:2W6/0:0)ChEBI
1-Eicosadienoyl-glycero-3-phosphocholineHMDB
1-(11Z,14Z-Eicosadienoyl)-glycero-3-phosphocholineHMDB
Chemical FormulaC28H54NO7P
Average Molecular Weight547.7046
Monoisotopic Molecular Weight547.363789599
IUPAC Name(2-{[(2R)-2-hydroxy-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-hydroxy-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COC(=O)CCCCCCCCC\C=C/C\C=C/CCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C28H54NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-28(31)34-25-27(30)26-36-37(32,33)35-24-23-29(2,3)4/h9-10,12-13,27,30H,5-8,11,14-26H2,1-4H3/b10-9-,13-12-/t27-/m1/s1
InChI KeyYYQVCMMXPIJVHY-ZOIJLGJPSA-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
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.81ALOGPS
logP2.25ChemAxon
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
Refractivity162.91 m³·mol⁻¹ChemAxon
Polarizability63.93 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 (Non-derivatized) - 70eV, Positivesplash10-01wb-4950300000-2b534c4b4962d0c5d7b1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0irc-9531012000-d0da97613071e6ee5db7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("LysoPC(20:2(11Z,14Z)/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, Positivesplash10-000l-9153130000-ddcdf9383ae85f003eb5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-8393010000-4f78c2b1cb1876be6217View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053i-9041000000-6634c7c13c38d10b8ec3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4s-0079170000-6a885f2f67af8e2a07d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0059200000-b3ead59dc812c921c7cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-9278000000-2d2972dbcef1738d4f77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0000090000-1175b76b2bc231897683View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-0900060000-7906987a44821eb7ef76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0910040000-49cc879526d35ed51c3dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000090000-037e7007a2a3a4d9c18aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-0000090000-9eb9db8d398748cd3a7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gw0-1609090000-cb38be36506577540632View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0003090000-0a9fa9f5e6fba84f6dbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1019010000-6b8bc97d2196dc2a7721View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0009000000-5728f2384b4de1f695b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000090000-cc957e670b89b93dbe1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-0009070000-6d4f3ca62c1a37b2cc34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0039030000-7405a981075daf5611d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000190000-1ac263e08790294aa9d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udk-0002990000-3e9832ff5ff17760a97cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v4j-0309400000-655bf984203c6b032e37View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0010392
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027543
KNApSAcK IDNot Available
Chemspider ID21403157
KEGG Compound IDC04230
BioCyc ID PHOSPHATIDYLCHOLINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52924053
PDB IDNot Available
ChEBI ID83055
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available