Showing metabocard for LysoPC(20:3(8Z,11Z,14Z)) (BMDB0010394)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:05:44 UTC
Update Date2020-06-04 19:39:57 UTC
BMDB IDBMDB0010394
Secondary Accession Numbers
  • BMDB10394
Metabolite Identification
Common NameLysoPC(20:3(8Z,11Z,14Z))
Description1-[(8Z,11Z,14Z)-icosatrienoyl]-sn-glycero-3-phosphocholine, also known as 1-dihomo-linolenoyl-GPC or 1-homo-gamma-linolenoyl-glycero-3-phosphocholine, 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. Thus, 1-[(8Z,11Z,14Z)-icosatrienoyl]-sn-glycero-3-phosphocholine is considered to be a glycerophosphocholine lipid molecule. 1-[(8Z,11Z,14Z)-icosatrienoyl]-sn-glycero-3-phosphocholine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-[(8Z,11Z,14Z)-Eicosatrienoyl]-sn-glycero-3-phosphocholineChEBI
1-Dihomo-linolenoyl-GPCChEBI
1-Dihomo-linolenoyl-GPC(20:3n6)ChEBI
1-Homo-gamma-linolenoyl-glycero-3-phosphocholineChEBI
GPC(20:3n6)ChEBI
GPC(20:3n6/0:0)ChEBI
LPC(20:3)ChEBI
LysoPC(20:3)ChEBI
Lysophosphatidylcholine(20:3)ChEBI
1-Homo-g-linolenoyl-glycero-3-phosphocholineGenerator
1-Homo-γ-linolenoyl-glycero-3-phosphocholineGenerator
LyPC(20:3/0:0)Lipid Annotator, HMDB
LysoPC(20:3(8Z,11Z,14Z))Lipid Annotator
LPC(20:3/0:0)Lipid Annotator, HMDB
LysoPC(20:3/0:0)Lipid Annotator, HMDB
LyPC(20:3)Lipid Annotator, HMDB
1-(8Z,11Z,14Z-eicosatrienoyl)-glycero-3-phosphocholineLipid Annotator, HMDB
Lysophosphatidylcholine(20:3/0:0)Lipid Annotator, HMDB
LPC(20:3n6/0:0)HMDB
LPC(20:3W6/0:0)HMDB
LyPC(20:3n6/0:0)HMDB
LyPC(20:3W6/0:0)HMDB
LysoPC a C20:3HMDB
LysoPC(20:3n6/0:0)HMDB
LysoPC(20:3W6/0:0)HMDB
Lysophosphatidylcholine(20:3n6/0:0)HMDB
Lysophosphatidylcholine(20:3W6/0:0)HMDB
1-Dihomo-gamma-linolenoyl-GPCHMDB
1-Dihomo-gamma-linolenoyl-lysophosphatidylcholineHMDB
1-Dihomo-gamma-linolenoyl-sn-glycero-3-phosphocholineHMDB
GPC(20:3(8Z,11Z,14Z))HMDB
GPC(20:3(8Z,11Z,14Z)/0:0)HMDB
GPC(20:3)HMDB
GPC(20:3w6)HMDB
GPC(20:3w6/0:0)HMDB
LPC(20:3(8Z,11Z,14Z))HMDB
LPC(20:3(8Z,11Z,14Z)/0:0)HMDB
LPC(20:3n6)HMDB
LPC(20:3w6)HMDB
LysoPC(20:3(8Z,11Z,14Z)/0:0)HMDB
LysoPC(20:3n6)HMDB
LysoPC(20:3w6)HMDB
Lysophosphatidylcholine(20:3(8Z,11Z,14Z))HMDB
Lysophosphatidylcholine(20:3(8Z,11Z,14Z)/0:0)HMDB
Lysophosphatidylcholine(20:3n6)HMDB
Lysophosphatidylcholine(20:3w6)HMDB
Chemical FormulaC28H52NO7P
Average Molecular Weight545.6887
Monoisotopic Molecular Weight545.348139535
IUPAC Name(2-{[(2R)-2-hydroxy-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-hydroxy-3-[(8Z,11Z,14Z)-icosa-8,11,14-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number1006703-11-2
SMILES
CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C28H52NO7P/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/h9-10,12-13,15-16,27,30H,5-8,11,14,17-26H2,1-4H3/b10-9-,13-12-,16-15-/t27-/m1/s1
InChI KeyBBNHCUBQEQJHIG-FZZJNMCHSA-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
logP2.65ALOGPS
logP1.89ChemAxon
logS-6.5ALOGPS
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 Count25ChemAxon
Refractivity164.03 m³·mol⁻¹ChemAxon
Polarizability61.74 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, Positivesplash10-007t-4940200000-539a8f6feb74a21a66dcView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0irc-9631012000-81b6c55072101312aa6aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("LysoPC(20:3(8Z,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, Positivesplash10-000i-9153130000-18fae725515f180cca64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-9484010000-be7a34a51ea184e42e3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9041000000-5ebe0c1f89b46b467f2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4u-0079170000-c78131971d03e5de90c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0059200000-7b3a58f9bbf54cc35ddcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-8279000000-17f06d050dc6537981baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000090000-2fa9e2dacbd579d98321View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-0000090000-4e0d8983cb3993c06087View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k9i-1609090000-d5aa77469dc8dbc46c34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000090000-91dea8ecfdf79e4e7a22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-0009070000-4ff84ef3f56eac796f10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0039030000-159be9a74a8e1e30d620View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0003090000-5f23f15b3d1cddc86c7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1019010000-f0ec184501a709e17d8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1009000000-33adea1b71d9d85ebe36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0000090000-bf7fc3df698e870dec69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-0900060000-e960f0563ba251b8e278View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fai-0910040000-a85b3fe6a7ba7ef759c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000190000-a0ae6730d99da9a4c0a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udo-0002990000-8cd2eede2fa4ae6a1a81View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0j4l-0309400000-92edf5aa3d34b1285d04View 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 Quantified1.6 +/- 0.3 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
LiverDetected and Quantified0.132 +/- 0.051 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Longissimus Thoracis MuscleDetected and Quantified0.05 +/- 0.01 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Ruminal FluidDetected and Quantified2 +/- 1 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Semimembranosus MuscleDetected and Quantified0.08 +/- 0.02 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
TestisDetected and Quantified0.04 +/- 0.01 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0010394
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID21403156
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52924055
PDB IDNot Available
ChEBI ID86256
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available