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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-16 13:20:10 UTC
Update Date2018-04-16 17:01:26 UTC
HMDB IDHMDB0010396
Secondary Accession Numbers
  • HMDB10396
Metabolite Identification
Common NameLysoPC(20:4(8Z,11Z,14Z,17Z))
DescriptionLysoPC(20:4(8Z,11Z,14Z,17Z)) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. 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(20:4(8Z,11Z,14Z,17Z)), in particular, consists of one chain of eicsoatetraenoic acid at the C-1 position. The eicsoatetraenoic acid moiety is derived from fish oils. 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. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-R's are members of the G protein-coupled receptor family of integral membrane proteins.
Structure
Thumb
Synonyms
ValueSource
1-Eicsoatetraenoyl-glycero-3-phosphocholineChEBI
LPC(20:4/0:0)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-phosphocholine; LysoPC(20:4)Lipid Annotator
LysoPC(20:4(8Z,11Z,14Z,17Z))Lipid Annotator
1-(8Z,11Z,14Z,17Z-eicosapentaenoyl)-glycero-3-phosphocholineLipid Annotator
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 phosphonato]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-hydroxy-3-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propyl phosphonato]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
ClassificationNot classified
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00029 g/LALOGPS
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
Polarizability61.28 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
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 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
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Location
  • All Tissues
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified6.13 +/- 2.55 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.26 +/- 0.14 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.255 +/- 0.142 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified12.6 (10.2-14.9) uMNewborn (0-30 days old)Not Available
Normal
details
BloodDetected and Quantified8.21(2.2) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified5.14 +/- 1.50 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified4.57 (3.56-5.89) uMInfant (0-1 year old)Not Available
Normal
details
BloodDetected and Quantified5.82 +/- 1.77 uMChildren (1-13 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.024 +/- 0.007 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected and Quantified0.19 +/- 0.22 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0.15 +/- 0.13 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.034 +/- 0.0008 uMAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified0.002 (0.0005-0.0038) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified4.2194 (3.7183) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified7.9856 (2.2556) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified4.8 +/- 1.4 uMChildren (1-13 years old)Both
Obese
details
BloodDetected and Quantified4.5 +/- 1.9 uMChildren (1-13 years old)Both
Obese
details
BloodDetected and Quantified4.5 +/- 1.7 uMChildren (1-13 years old)Both
Obese
details
BloodDetected and Quantified4.7 +/- 2.0 uMChildren (1-13 years old)Both
Obese
details
BloodDetected and Quantified7.06(2.24) uMAdult (>18 years old)BothHeart failure with reduced ejection fraction details
BloodDetected and Quantified4.4 +/- 1.21 uMChildren (1-13 years old)Both
Obese
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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

Only showing the first 10 proteins. There are 25 proteins in total.

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has depalmitoylating activity and also low lysophospholipase activity.
Gene Name:
LYPLA1
Uniprot ID:
O75608
Molecular weight:
24669.355
General function:
Involved in phosphatidylcholine-sterol O-acyltransferase activity
Specific function:
Has transacylase and calcium-independent phospholipase A2 activity. Catalyzes the formation of 1-O-acyl-N-acetylsphingosine and the concomitant release of a lyso-phospholipid (By similarity). May have weak lysophospholipase activity.
Gene Name:
PLA2G15
Uniprot ID:
Q8NCC3
Molecular weight:
Not Available
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. This isozyme hydrolyzes more efficiently L-alpha-1-palmitoyl-2-oleoyl phosphatidylcholine than L-alpha-1-palmitoyl-2-arachidonyl phosphatidylcholine, L-alpha-1-palmitoyl-2-arachidonyl phosphatidylethanolamine, or L-alpha-1-stearoyl-2-arachidonyl phosphatidylinositol. May be involved in the production of lung surfactant, the remodeling or regulation of cardiac muscle.
Gene Name:
PLA2G5
Uniprot ID:
P39877
Molecular weight:
15674.065
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Hydrolyzes phosphatidylglycerol versus phosphatidylcholine with a 15-fold preference.
Gene Name:
PLA2G2F
Uniprot ID:
Q9BZM2
Molecular weight:
23256.29
General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular weight:
85210.19
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Molecular weight:
16359.535
General function:
Involved in phospholipase A2 activity
Specific function:
Not known; does not seem to have catalytic activity.
Gene Name:
PLA2G12B
Uniprot ID:
Q9BX93
Molecular weight:
Not Available
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:
PLA2G10
Uniprot ID:
O15496
Molecular weight:
18153.04
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Molecular weight:
15988.525
General function:
Involved in hydrolase activity
Specific function:
May hydrolyze fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has lysophospholipase activity (By similarity). Deacylates GAP43.
Gene Name:
LYPLA2
Uniprot ID:
O95372
Molecular weight:
24736.71

Only showing the first 10 proteins. There are 25 proteins in total.