Showing metabocard for LysoPC(20:1(11Z)) (BMDB0010391)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:05:41 UTC
Update Date2020-05-11 19:11:14 UTC
BMDB IDBMDB0010391
Secondary Accession Numbers
  • BMDB10391
Metabolite Identification
Common NameLysoPC(20:1(11Z))
DescriptionLysoPC(20:1(11Z)/0:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. LysoPC(20:1(11Z)/0:0), in particular, consists of one 11Z-eicosenoyl 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-{[(2R)-2-hydroxy-3-[(11Z)-icos-11-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazaniumChEBI
1-(11Z)-Eicosenoyl-sn-glycero-3-phosphocholineChEBI
1-(11Z-Eicosenoyl)-glycero-3-phosphocholineChEBI
LPC(20:1n9/0:0)ChEBI
LPC(20:1W9/0:0)ChEBI
LyPC(20:1n9/0:0)ChEBI
LyPC(20:1W9/0:0)ChEBI
LysoPC(20:1(11Z))ChEBI
LysoPC(20:1n9/0:0)ChEBI
LysoPC(20:1W9/0:0)ChEBI
Lysophosphatidylcholine(20:1n9/0:0)ChEBI
Lysophosphatidylcholine(20:1W9/0:0)ChEBI
1-Eicosenoyl-glycero-3-phosphocholineHMDB
LPC(20:1)HMDB
LPC(20:1/0:0)HMDB
LyPC(20:1)HMDB
LyPC(20:1/0:0)HMDB
LysoPC(20:1)HMDB
LysoPC(20:1/0:0)HMDB
Lysophosphatidylcholine(20:1)HMDB
Lysophosphatidylcholine(20:1/0:0)HMDB
1-(11-Eicosenoyl)-glycero-3-phosphocholineHMDB
1-EicosenoylglycerophosphocholineHMDB
Chemical FormulaC28H56NO7P
Average Molecular Weight549.7205
Monoisotopic Molecular Weight549.379439663
IUPAC Name(2-{[(2R)-2-hydroxy-3-[(11Z)-icos-11-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-hydroxy-3-[(11Z)-icos-11-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/CCCCCCCCCC(=O)OC[C@@]([H])(O)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C28H56NO7P/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/h12-13,27,30H,5-11,14-26H2,1-4H3/b13-12-/t27-/m1/s1
InChI KeyYYSFWGQAKJTHRE-MEOKJUQFSA-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
logP2.99ALOGPS
logP2.61ChemAxon
logS-6.7ALOGPS
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 Count27ChemAxon
Refractivity161.79 m³·mol⁻¹ChemAxon
Polarizability64.92 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, Positivesplash10-007k-5950200000-c36e424a9883695ffe04View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-06y6-9421001000-6ec6e9a5ee6bc2677abcView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("LysoPC(20:1(11Z)/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-9153130000-7577ddc9070b1b04a70aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ko-8393010000-f0dad899a83fe3039151View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053i-9041000000-8d16d370e1b711c3f120View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052e-0079170000-d0e7eb8a24adc6645029View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-0059200000-aba75b96e96e22cd22e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-8279000000-41bdafb1096ca976781dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000090000-ff3e5c84bede67d8e291View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-0009070000-8fbb2ec392bf51ce4a88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0039030000-e18cedcc015394934b9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000090000-439a9fa5ef8a94dc7f9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-0000090000-560f4f537d0c4278fbeaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gw0-1609090000-d8f3402356b14005b851View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000190000-29e78db902a00a1156b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4k-0002990000-b6b0175e971309c9813eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gi1-0309400000-ee39aed0293cd06ac57dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0000090000-7fd706dfd03fd63feefdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0900060000-8ea4488f7f1864cd11c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f89-0910040000-2fdd792a3557e698d653View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0003090000-4abecc60e7222e976625View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1019010000-0a6fdb366821861ef02fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0009000000-e298cde05e6626094c71View 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 IDHMDB0010391
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027542
KNApSAcK IDNot Available
Chemspider ID24766530
KEGG Compound IDC04230
BioCyc ID PHOSPHATIDYLCHOLINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52924051
PDB IDNot Available
ChEBI ID88685
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available