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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-16 13:20:09 UTC
Update Date2020-02-27 16:51:29 UTC
HMDB IDHMDB0010395
Secondary Accession Numbers
  • HMDB10395
Metabolite Identification
Common NameLysoPC(20:4(5Z,8Z,11Z,14Z)/0:0)
DescriptionLysoPC(20:4(5Z,8Z,11Z,14Z)) 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(5Z,8Z,11Z,14Z)), in particular, consists of one chain of arachidonic acid at the C-1 position. The arachidonic acid moiety is derived from animal fats and eggs. 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
Data?1582752823
Synonyms
ValueSource
1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-sn-glycero-3-phosphocholineChEBI
1-Arachidonoyl-glycero-3-phosphocholineChEBI
1-Arachidonoyl-GPCChEBI
GPC(20:4n6)ChEBI
LPC 20:4(5Z,8Z,11Z,14Z)/0:0ChEBI
LPC(20:4(5Z,8Z,11Z,14Z)/0:0)ChEBI
LysoPC 20:4(5Z,8Z,11Z,14Z)/0:0ChEBI
Lysophosphatidylcholine(20:4(5Z,8Z,11Z,14Z)/0:0)ChEBI
PC 20:4(5Z,8Z,11Z,14Z)/0:0ChEBI
PC(20:4(5Z,8Z,11Z,14Z)/0:0)ChEBI
LPC(20:4)HMDB
LPC(20:4/0:0)HMDB
LPC(20:4n6/0:0)HMDB
LPC(20:4W6/0:0)HMDB
LyPC(20:4)HMDB
LyPC(20:4/0:0)HMDB
LyPC(20:4n6/0:0)HMDB
LyPC(20:4W6/0:0)HMDB
LysoPC a C20:4HMDB
LysoPC(20:4)HMDB
LysoPC(20:4/0:0)HMDB
LysoPC(20:4n6/0:0)HMDB
LysoPC(20:4W6/0:0)HMDB
Lysophosphatidylcholine(20:4)HMDB
Lysophosphatidylcholine(20:4/0:0)HMDB
Lysophosphatidylcholine(20:4n6/0:0)HMDB
Lysophosphatidylcholine(20:4W6/0:0)HMDB
LysoPC(20:4(5Z,8Z,11Z,14Z))HMDB
1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-glycero-3-phosphocholineHMDB
LysoPC(20:4(5Z,8Z,11Z,14Z)/0:0)ChEBI
1-ArachidonoylglycerophosphocholineHMDB
Chemical FormulaC28H50NO7P
Average Molecular Weight543.6729
Monoisotopic Molecular Weight543.332489471
IUPAC Name(2-{[(2R)-2-hydroxy-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-hydroxy-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number60701-99-7
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OC[C@@H](O)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/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 KeyLAXQYRRMGGEGOH-JXRLJXCWSA-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
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
logP2.45ALOGPS
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
Polarizability60.98 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05aj-5960300000-0ee5b67c6a037e94173aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0feu-9441012000-f0e3e2a8c8b160e8afdbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-9153130000-d52f673521111b5098b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-8394010000-35345158b0e85dd92443Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-9041000000-d2cf76f6124369da1f61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udu-0079170000-3ec998bd7f23091d2628Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0059200000-813e63ff71fa72c208d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ug0-9288000000-186fc82c9c4a804dd090Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • All Tissues
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified6.13 +/- 2.55 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified8.39 +/- 0.98 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified2.20-11.0 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified8.394 +/- 0.976 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)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified0.002 (0.0005-0.0038) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0037 +/- 0.0022 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.0-0.03 umol/mmol creatinineNewborn (0-30 days old)BothNormal
    • López Hernández Y...
details
UrineDetected and Quantified0.0(0.0-0.02) umol/mmol creatinineNewborn (0-30 days old)FemaleNormal
    • López Hernández Y...
details
UrineDetected and Quantified0.0(0.0-0.03) umol/mmol creatinineNewborn (0-30 days old)MaleNormal
    • López Hernández Y...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
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
UrineDetected and Quantified0.0034 +/- 0.003 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0.0026 +/- 0.0027 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Pregnancy
  1. Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Obesity
  1. Reinehr T, Wolters B, Knop C, Lass N, Hellmuth C, Harder U, Peissner W, Wahl S, Grallert H, Adamski J, Illig T, Prehn C, Yu Z, Wang-Sattler R, Koletzko B: Changes in the serum metabolite profile in obese children with weight loss. Eur J Nutr. 2015 Mar;54(2):173-81. doi: 10.1007/s00394-014-0698-8. Epub 2014 Apr 17. [PubMed:24740590 ]
  2. Wahl S, Yu Z, Kleber M, Singmann P, Holzapfel C, He Y, Mittelstrass K, Polonikov A, Prehn C, Romisch-Margl W, Adamski J, Suhre K, Grallert H, Illig T, Wang-Sattler R, Reinehr T: Childhood obesity is associated with changes in the serum metabolite profile. Obes Facts. 2012;5(5):660-70. doi: 10.1159/000343204. Epub 2012 Oct 4. [PubMed:23108202 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB027546
KNApSAcK IDNot Available
Chemspider ID21403155
KEGG Compound IDC04230
BioCyc ID PHOSPHATIDYLCHOLINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24779476
PDB IDNot Available
ChEBI ID74344
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

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.