Showing metabocard for LysoPC(0:0/20:4(5Z,8Z,11Z,14Z)) (BMDB0109696)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2020-05-06 19:41:25 UTC
Update Date2020-05-07 14:45:05 UTC
BMDB IDBMDB0109696
Secondary Accession NumbersNone
Metabolite Identification
Common NameLysoPC(0:0/20:4(5Z,8Z,11Z,14Z))
DescriptionLysoPC(0:0/20:4(5Z,8Z,11Z,14Z)) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. LysoPC(0:0/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one 5Z,8Z,11Z,14Z-eicosatetraenoyl 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
2-(5Z,8Z,11Z,14Z)-Eicosatetraenoyl-sn-glycero-3-phosphocholineChEBI
2-(5Z,8Z,11Z,14Z)-Icosatetraenoyl-sn-glycero-3-phosphocholineChEBI
2-Arachidonoyl-GPCChEBI
2-ArachidonoyllysophosphatidylcholineChEBI
GPC(0:0/20:4)ChEBI
GPC(20:4)ChEBI
LPC(0:0/20:4(5Z,8Z,11Z,14Z))ChEBI
PC(0:0/20:4(5Z,8Z,11Z,14Z))ChEBI
2-ALPCHMDB
2-Arachidonoylglycero-3-phosphocholineHMDB
2-Arachidonoyl-lysopcHMDB
2-Arachidonoyl-lysophosphatidylcholineHMDB
2-Arachidonoyl-sn-glycero-3-phosphocholineHMDB
GPC(0:0/20:4(5Z,8Z,11Z,14Z))HMDB
GPC(0:0/20:4n6)HMDB
GPC(0:0/20:4W6)HMDB
GPC(20:4(5Z,8Z,11Z,14Z))HMDB
GPC(20:4n6)HMDB
GPC(20:4W6)HMDB
LPC(0:0/20:4n6)HMDB
LPC(0:0/20:4W6)HMDB
LPC(20:4(5Z,8Z,11Z,14Z))HMDB
LPC(20:4)HMDB
LPC(20:4n6)HMDB
LPC(20:4W6)HMDB
LysoPC(0:0/20:4n6)HMDB
LysoPC(0:0/20:4W6)HMDB
LysoPC(20:4(5Z,8Z,11Z,14Z))HMDB
LysoPC(20:4)HMDB
LysoPC(20:4n6)HMDB
LysoPC(20:4W6)HMDB
Lysophosphatidylcholine(0:0/20:4(5Z,8Z,11Z,14Z))HMDB
Lysophosphatidylcholine(0:0/20:4n6)HMDB
Lysophosphatidylcholine(0:0/20:4W6)HMDB
Lysophosphatidylcholine(20:4(5Z,8Z,11Z,14Z))HMDB
Lysophosphatidylcholine(20:4)HMDB
Lysophosphatidylcholine(20:4n6)HMDB
Lysophosphatidylcholine(20:4W6)HMDB
LysoPC(0:0/20:4(5Z,8Z,11Z,14Z))HMDB
Chemical FormulaC28H50NO7P
Average Molecular Weight543.682
Monoisotopic Molecular Weight543.332489952
IUPAC Name(2-{[(2R)-3-hydroxy-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-hydroxy-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)O[C@H](CO)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C28H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-28(31)36-27(25-30)26-35-37(32,33)34-24-23-29(2,3)4/h9-10,12-13,15-16,18-19,27,30H,5-8,11,14,17,20-26H2,1-4H3/b10-9-,13-12-,16-15-,19-18-/t27-/m1/s1
InChI KeyIGJKYDBBINVMLH-JXRLJXCWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-2 position, and linked at position 3 to a phosphocholine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent2-acyl-sn-glycero-3-phosphocholines
Alternative Parents
Substituents
  • 2-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
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary alcohol
  • 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
logP2.41ALOGPS
logP1.52ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area105.12 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity165.14 m³·mol⁻¹ChemAxon
Polarizability60.42 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 (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("LysoPC(0:0/20:4(5Z,8Z,11Z,14Z)),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000090000-a2148247656f403ba19dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udl-1009270000-b010f321f313d468c81bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufr-7209200000-dbbb21f62dfe22412f8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0200090000-627e9903305e965c7dddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1900010000-47424bbbaa438461b3dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-008i-4900000000-3516e1a24113b9d9b18eView 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 IDHMDB0061699
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID21403158
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52924038
PDB IDNot Available
ChEBI ID76079
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available