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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-09-16 13:20:00 UTC
Update Date2023-07-07 20:53:58 UTC
HMDB IDHMDB0010386
Secondary Accession Numbers
  • HMDB0061692
  • HMDB10386
  • HMDB61692
Metabolite Identification
Common NameLysoPC(18:2/0:0)
DescriptionLysoPC(18:2(9Z,12Z)) 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(18:2(9Z,12Z)), in particular, consists of one chain of linoleic acid at the C-1 position. The linoleic acid moiety is derived from seed 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 (GPR) family of integral membrane proteins. Lysophosphatidylcholines (LPCs) specifically bind to GPR119, GPR40, GPR55 and GPR4.  binding of LPCs to GPR119, GPR40 and GPR55 induces intracellular calcium mobilization and leads to increased glucose-stimulated insulin secretion in different cell systems. In blood or plasma LPCs are bound mainly to albumin and to a lesser extent to lipoproteins. Inflammation, cell damage and other pathophysiological conditions can profoundly alter the ratio of free to albumin bound LPC through increased production of LPC or decreased plasma levels of albumin (PMID: 32599910 ). In particular, lower levels of albumin (hypoalbuminemia) lead to lower levels of LPC in the blood.  Hypoalbuminemia with albumin concentrations of <20 g/L are typical of patients with sepsis, burns or serious trauma (PMID: 26557421 ). Such low levels of albumin often lead to LPC levels that are 50-80 % lower than that seen in healthy individuals (PMID: 27501420 ). Decreased levels of LPC have been observed in a number of other inflammatory conditions beyond sepsis, including rheumatoid arthritis, diabetes, schizophrenia, polycystic ovary syndrome, Alzheimer’s disease, pulmonary arterial hypertension, aging, asthma and liver cirrhosis, where they were associated with increased mortality risk (PMID: 32599910 ).  LPCs have a number of protective or anti-inflammatory effects.  Higher levels of LPC induce cyclooxygenase-2 and endothelial nitric oxide synthase (eNOS) expression in endothelial cells, both of which can have vasoprotective effects either via production of prostacyclin or nitric oxide (PMID: 32599910 ). LPCs have been shown to elicit a number of effects on the innate immune system and effectively serve as dual-activity ligand molecules. In particular, LPCs directly activate toll-like receptor (TLR) 4 and TLR-2-1 receptors in the absence of classical TLR ligands. However, LPCs can also inhibit TLR-mediated signaling in the presence of classical TLR ligands, thereby acting as anti-inflammatory molecules (PMID: 32599910 ).  Low levels of LPC during a bacterial or viral infection with TLR-mediated signalling can lead to opposing (inflammatory vs. anti-inflammatory) effects and immune dysregulation.
Structure
Data?1660688719
Synonyms
ValueSource
1-(9Z,12Z)-Octadecadienoyl-sn-glycero-3-phosphocholineChEBI
1-(9Z,12Z-Octadecadienoyl)-glycero-3-phosphocholineChEBI
1-(9Z,12Z-Octadecadienoyl)-sn-glycero-3-phosphocholineChEBI
1-18:2-LysoPCChEBI
1-Linoleoyl-glycero-3-phosphocholineChEBI
1-Linoleoyl-GPCChEBI
1-Linoleoyl-GPC (18:2)ChEBI
1-LinoleoylglycerophosphocholineChEBI
GPC(18:2)ChEBI
GPC(18:2/0:0)ChEBI
LPC 18:2(9Z,12Z)/0:0ChEBI
LPC(18:2)ChEBI
LPC(18:2/0:0)ChEBI
LPC(18:2n6/0:0)ChEBI
LPC(18:2Omega6/0:0)ChEBI
LyPC(18:2)ChEBI
LyPC(18:2n6/0:0)ChEBI
LyPC(18:2omega6/0:0)ChEBI
LysoPC 18:2(9Z,12Z)/0:0ChEBI
LysoPC(18:2)ChEBI
LysoPC(18:2/0:0)ChEBI
LysoPC(18:2n6/0:0)ChEBI
LysoPC(18:2omega6/0:0)ChEBI
Lysophosphatidylcholine(18:2(9Z,12Z)/0:0)ChEBI
Lysophosphatidylcholine(18:2)ChEBI
Lysophosphatidylcholine(18:2/0:0)ChEBI
Lysophosphatidylcholine(18:2n6/0:0)ChEBI
Lysophosphatidylcholine(18:2omega6/0:0)ChEBI
PC 18:2(9Z,12Z)/0:0ChEBI
PC(18:2(9Z,12Z)/0:0)ChEBI
LyPC(18:2/0:0)HMDB
LysoPC(18:2(9Z,12Z))HMDB
1-Linoleoyl lysolecithinHMDB
1-Linoleoyl-sn-glycero-3-phosphorylcholineHMDB
1-Linoleoylglycerol-3-phosphorylcholineHMDB
1-LinoleoylphosphatidylcholineHMDB
LinoleoyllysolecithinHMDB
Linoleyl lysophosphatidylcholineHMDB
Lysophosphatidylcholine 18:2HMDB
1-Linoleoyl-lysophosphatidylcholineHMDB
1-Linoleoyl-sn-glycero-3-phosphocholineHMDB
GPC(18:2(9Z,12Z))HMDB
GPC(18:2(9Z,12Z)/0:0)HMDB
GPC(18:2n6)HMDB
GPC(18:2n6/0:0)HMDB
GPC(18:2W6)HMDB
GPC(18:2W6/0:0)HMDB
LPC(18:2(9Z,12Z))HMDB
LPC(18:2(9Z,12Z)/0:0)HMDB
LPC(18:2n6)HMDB
LPC(18:2W6)HMDB
LPC(18:2W6/0:0)HMDB
LysoPC(18:2n6)HMDB
LysoPC(18:2W6)HMDB
LysoPC(18:2W6/0:0)HMDB
Lysophosphatidylcholine(18:2(9Z,12Z))HMDB
Lysophosphatidylcholine(18:2n6)HMDB
Lysophosphatidylcholine(18:2W6)HMDB
Lysophosphatidylcholine(18:2W6/0:0)HMDB
LysoPC(18:2(9Z,12Z)/0:0)ChEBI
Chemical FormulaC26H50NO7P
Average Molecular Weight519.6515
Monoisotopic Molecular Weight519.332489471
IUPAC Name(2-{[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number22252-07-9
SMILES
[H][C@@](O)(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C26H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)32-23-25(28)24-34-35(30,31)33-22-21-27(2,3)4/h9-10,12-13,25,28H,5-8,11,14-24H2,1-4H3/b10-9-,13-12-/t25-/m1/s1
InChI KeySPJFYYJXNPEZDW-FTJOPAKQSA-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
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00026 g/LALOGPS
logP2.22ALOGPS
logP1.36ChemAxon
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
Refractivity153.71 m³·mol⁻¹ChemAxon
Polarizability58.75 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+237.47830932474
DeepCCS[M-H]-234.21830932474
DeepCCS[M-2H]-268.47330932474
DeepCCS[M+Na]+244.97530932474
AllCCS[M+H]+233.632859911
AllCCS[M+H-H2O]+232.332859911
AllCCS[M+NH4]+234.832859911
AllCCS[M+Na]+235.232859911
AllCCS[M-H]-229.132859911
AllCCS[M+Na-2H]-232.332859911
AllCCS[M+HCOO]-235.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LysoPC(18:2(9Z,12Z)/0:0)CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C3844.8Standard polar33892256
LysoPC(18:2(9Z,12Z)/0:0)CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C3026.0Standard non polar33892256
LysoPC(18:2(9Z,12Z)/0:0)CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C3480.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
LysoPC(18:2(9Z,12Z)/0:0),1TMS,isomer #1CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C3500.4Semi standard non polar33892256
LysoPC(18:2(9Z,12Z)/0:0),1TBDMS,isomer #1CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C3730.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - LysoPC(18:2/0:0) GC-MS (1 TMS) - 70eV, Positivesplash10-03kl-9431010000-c20360afbdedc9d9232f2017-10-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(18:2/0:0) 10V, Positive-QTOFsplash10-004i-0000190000-3c86eb832bb0e5b457ff2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(18:2/0:0) 20V, Positive-QTOFsplash10-0190-0002990000-61bb2de3bf360b7c57842021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(18:2/0:0) 40V, Positive-QTOFsplash10-0frl-0309400000-703f583c1dec34d853632021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(18:2/0:0) 10V, Positive-QTOFsplash10-0fk9-0000090000-971f1431e3c2228b9f5d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(18:2/0:0) 20V, Positive-QTOFsplash10-0089-0900060000-dd4dca9634d21e863fe42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(18:2/0:0) 40V, Positive-QTOFsplash10-0ue9-0910040000-75b3d9cd99357a6300432021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(18:2/0:0) 10V, Negative-QTOFsplash10-014i-0030090000-9b4f9f161f1e634d70b62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(18:2/0:0) 20V, Negative-QTOFsplash10-004i-1090010000-2378656ce1b1501e42df2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(18:2/0:0) 40V, Negative-QTOFsplash10-004i-1090000000-ed0e0c463537d6bd8f932021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(18:2/0:0) 10V, Positive-QTOFsplash10-0006-0000190000-85bff21ad2f9c91a74472021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(18:2/0:0) 20V, Positive-QTOFsplash10-001l-0001960000-38c8f8d665d29a3102862021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(18:2/0:0) 40V, Positive-QTOFsplash10-0pcr-1609710000-e08a75389116b197e7742021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(18:2/0:0) 10V, Negative-QTOFsplash10-0udi-0000090000-7d81a037787f63d958552021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(18:2/0:0) 20V, Negative-QTOFsplash10-0fb9-0090070000-6e0343e152dc3c713a982021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPC(18:2/0:0) 40V, Negative-QTOFsplash10-004i-0090020000-20568d21d5462d55a6c02021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • All Tissues
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified30.33 +/- 10.3 uMAdult (>18 years old)Both
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified52.75 +/- 6.48 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified7.00-59.0 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified52.755 +/- 6.478 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified9.17 (7.36-11) uMNewborn (0-30 days old)Not Available
Normal
details
BloodDetected and Quantified37.27(10.8) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified26.6 +/- 9.20 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified24.9 (19.7-33.1) uMInfant (0-1 year old)Not Available
Normal
details
BloodDetected and Quantified36.37 +/- 11.44 uMChildren (1-13 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected and Quantified3 +/- 3.15 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified4.15 +/- 5.33 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0072 +/- 0.0043 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected and Quantified0.0-0.03 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified0.01(0.0-0.03) umol/mmol creatinineNewborn (0-30 days old)FemaleNormal details
UrineDetected and Quantified0.0(0.0-0.03) umol/mmol creatinineNewborn (0-30 days old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Schizophrenia
details
BloodDetected and Quantified2.1(0.5-6.5) uMAdult (>18 years old)BothSepsis details
BloodDetected and Quantified21.7 +/- 7.7 uMChildren (1-13 years old)Both
Obese
details
BloodDetected and Quantified20.0 +/- 9.5 uMChildren (1-13 years old)Both
Obese
details
BloodDetected and Quantified19.6 +/- 8.2 uMChildren (1-13 years old)Both
Obese
details
BloodDetected and Quantified20.6 +/- 7.5 uMChildren (1-13 years old)Both
Obese
details
BloodDetected and Quantified28.23(8.39) uMAdult (>18 years old)BothHeart failure with preserved ejection fraction details
BloodDetected and Quantified31.52(11.38) uMAdult (>18 years old)BothHeart failure with reduced ejection fraction details
BloodDetected and Quantified17.582 (17.132) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified18.09 +/- 5.07 uMChildren (1-13 years old)Both
Obese
details
BloodDetected and Quantified36.345 (14.315) uMAdult (>18 years old)FemalePregnancy details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Bothliver cirrhosis details
UrineDetected and Quantified0.0055 +/- 0.0028 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified0.0065 +/- 0.0083 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Analysis of 30 no...
details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Cai HL, Li HD, Yan XZ, Sun B, Zhang Q, Yan M, Zhang WY, Jiang P, Zhu RH, Liu YP, Fang PF, Xu P, Yuan HY, Zhang XH, Hu L, Yang W, Ye HS: Metabolomic analysis of biochemical changes in the plasma and urine of first-episode neuroleptic-naive schizophrenia patients after treatment with risperidone. J Proteome Res. 2012 Aug 3;11(8):4338-50. doi: 10.1021/pr300459d. Epub 2012 Jul 26. [PubMed:22800120 ]
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 ]
Sepsis
  1. Ferrario M, Cambiaghi A, Brunelli L, Giordano S, Caironi P, Guatteri L, Raimondi F, Gattinoni L, Latini R, Masson S, Ristagno G, Pastorelli R: Mortality prediction in patients with severe septic shock: a pilot study using a target metabolomics approach. Sci Rep. 2016 Feb 5;6:20391. doi: 10.1038/srep20391. [PubMed:26847922 ]
Cirrhosis
  1. Huang HJ, Zhang AY, Cao HC, Lu HF, Wang BH, Xie Q, Xu W, Li LJ: Metabolomic analyses of faeces reveals malabsorption in cirrhotic patients. Dig Liver Dis. 2013 Aug;45(8):677-82. doi: 10.1016/j.dld.2013.01.001. Epub 2013 Feb 4. [PubMed:23384618 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030316
KNApSAcK IDNot Available
Chemspider ID9181014
KEGG Compound IDNot Available
BioCyc IDCPD-8347
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11005824
PDB IDNot Available
ChEBI ID28733
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00030042
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
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Only showing the first 10 proteins. There are 29 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 29 proteins in total.