Showing metabocard for LysoPC(20:4(8Z,11Z,14Z,17Z)) (BMDB0010396)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:05:46 UTC
Update Date2020-06-04 19:26:35 UTC
BMDB IDBMDB0010396
Secondary Accession Numbers
  • BMDB10396
Metabolite Identification
Common NameLysoPC(20:4(8Z,11Z,14Z,17Z))
DescriptionLysoPC(20:4(8Z,11Z,14Z,17Z)/0:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. LysoPC(20:4(8Z,11Z,14Z,17Z)/0:0), in particular, consists of one 8Z,11Z,14Z,17Z-eicosapentaenoyl 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-Eicsoatetraenoyl-glycero-3-phosphocholineChEBI
LPC(20:4/0:0)ChEBI
LysoPC(20:4(8Z,11Z,14Z,17Z))ChEBI
LysoPC(20:4/0:0)ChEBI
Lysophosphatidylcholine(20:4/0:0)ChEBI
1-EicsoateHMDB
1-Eicsoic acidHMDB
LPC(20:4)HMDB
LPC(20:4n3/0:0)HMDB
LPC(20:4W3/0:0)HMDB
LyPC(20:4)HMDB
LyPC(20:4/0:0)HMDB
LyPC(20:4n3/0:0)HMDB
LyPC(20:4W3/0:0)HMDB
LysoPC a C20:4HMDB
LysoPC(20:4)HMDB
LysoPC(20:4n3/0:0)HMDB
LysoPC(20:4W3/0:0)HMDB
Lysophosphatidylcholine(20:4)HMDB
Lysophosphatidylcholine(20:4n3/0:0)HMDB
Lysophosphatidylcholine(20:4W3/0:0)HMDB
1-(8Z,11Z,14Z,17Z-Eicosapentaenoyl)-glycero-3-phosphocholineHMDB
1-EicsoatetraenoylglycerophosphocholineHMDB
Chemical FormulaC28H50NO7P
Average Molecular Weight543.6729
Monoisotopic Molecular Weight543.332489471
IUPAC Name(2-{[(2R)-2-hydroxy-3-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-hydroxy-3-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CC\C=C/C\C=C/C\C=C/C\C=C/CCCCCCC(=O)OC[C@](O)([H])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)34-25-27(30)26-36-37(32,33)35-24-23-29(2,3)4/h6-7,9-10,12-13,15-16,27,30H,5,8,11,14,17-26H2,1-4H3/b7-6-,10-9-,13-12-,16-15-/t27-/m1/s1
InChI KeyGOMVPVRDBLLHQC-VEJNOCSESA-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 and Quantified
OriginNot Available
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
logP2.41ALOGPS
logP1.52ChemAxon
logS-6.3ALOGPS
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 Count24ChemAxon
Refractivity165.14 m³·mol⁻¹ChemAxon
Polarizability61.24 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, Positivesplash10-05a2-4950200000-5f3ea1281b366fbf0bf0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0h2u-9631002000-548020bf93f9ae06ef9bView in MoNA
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(20:4(8Z,11Z,14Z,17Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-9153130000-d52f673521111b5098b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9383010000-e6c78f8dd918cdfd3908View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-9041000000-8835fa70061dabb71b87View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udu-0079170000-3ec998bd7f23091d2628View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0059200000-8a262b7e1a3a9274ec32View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ug0-9288000000-824a302e9a9fcf612010View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000190000-77ea54490e84a8b3b537View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udo-0002990000-bf882252024772103db4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0j4l-0309400000-b3d902f7c0961b2949cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000090000-3472f30822b8e8601036View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-0000090000-36674ea865affe2dc312View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pcr-1609090000-dfdd3aa00d18d17c8130View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000090000-0fde8b52b527d51cb487View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufr-0009070000-40ae7eb8536816f65fefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0039030000-a665ab26fc9f4e63275eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0003090000-6ea8042d7f2a61358243View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1029010000-b64d2c578dde5bd000a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-1009000000-235bb8cd3066c2669beaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0000090000-b4c66c94aa69a4a40271View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0900060000-53fafe765bf1daa88e60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fai-0910040000-d12a6e3ffba0751a322dView 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 Quantified0.48 +/- 0.14 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
LiverDetected and Quantified0.41 +/- 0.11 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Longissimus Thoracis MuscleDetected and Quantified0.07 +/- 0.03 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Ruminal FluidDetected and Quantified0.09 +/- 0.02 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.03 +/- 0.02 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Semimembranosus MuscleDetected and Quantified0.09 +/- 0.03 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
TestisDetected and Quantified0.2 +/- 0.1 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0010396
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027547
KNApSAcK IDNot Available
Chemspider ID24766532
KEGG Compound IDC04230
BioCyc ID PHOSPHATIDYLCHOLINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480469
PDB IDNot Available
ChEBI ID86259
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available