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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-09-16 13:19:56 UTC
Update Date2022-08-16 21:56:12 UTC
HMDB IDHMDB0010382
Secondary Accession Numbers
  • HMDB0062541
  • HMDB10382
  • HMDB62541
Metabolite Identification
Common NameLysoPC(16:0/0:0)
DescriptionLysoPC(16:0) 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(16:0), in particular, consists of one chain of palmitic acid at the C-1 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. 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?1660686972
Synonyms
ValueSource
(2R)-2-Hydroxy-3-(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphateChEBI
1-16:0-LysoPCChEBI
1-16:0-LysophosphatidylcholineChEBI
1-Hexadecanoyl-2-lysophosphatidylcholineChEBI
1-Palmitoyl-2-hydroxy-sn-glycero-3-phosphocholineChEBI
1-Palmitoyl-2-lysophosphatidylcholineChEBI
1-Palmitoyl-GPCChEBI
1-Palmitoyl-GPC (16:0)ChEBI
1-Palmitoyl-phosphatidylcholineChEBI
1-Palmitoyl-sn-glycero-3-phosphocholineChEBI
1-PalmitoylphosphatidylcholineChEBI
16:0 LYSO-PCChEBI
GPC(16:0)ChEBI
GPC(16:0/0:0)ChEBI
GPCho 16:0/0:0ChEBI
GPCho(16:0/0:0)ChEBI
LPC 16:0/0:0ChEBI
LPC(16:0)ChEBI
LPC(16:0/0:0)ChEBI
LyPC(16:0)ChEBI
LyPC(16:0/0:0)ChEBI
LysoPC 16:0/0:0ChEBI
LysoPC(16:0)ChEBI
Lysophosphatidylcholine(16:0)ChEBI
Lysophosphatidylcholine(16:0/0:0)ChEBI
PC(16:0/0:0)ChEBI
(2R)-2-Hydroxy-3-(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphoric acidGenerator
1-Palmitoyl-glycero-3-phosphocholineHMDB
1-Palmitoyl-lysophosphatidylcholineHMDB
LysoPC a C16:0HMDB
1-Pam-2-lysoptdchoHMDB
1-Hexadecanoyl-glycero-3-phosphocholineHMDB
1-Palmitoyl-sn-glycerol-3-phosphorylcholineHMDB
1-Palmitoylglycerol-3-phosphorylcholineHMDB
Hydroxide inner salt(S)-isomer OF we 201HMDB
1-O-Hexadecylpropanediol 3-phosphorylcholineHMDB
1-PalmitoyllysophosphatidylcholineHMDB
LYSO-PCHMDB
Hydroxide inner salt(R)-isomer OF we 201HMDB
Hydroxide inner salt(+-)-isomer OF we 201HMDB
Palmitoyl lysophosphatidylcholineHMDB
1-HexadecanoylglycerophosphocholineHMDB
1-PalmitoylglycerophosphocholineHMDB
1-Hexadecanoyl-sn-glycero-3-phosphocholineHMDB
1-Hexadecanoyl-sn-glycerol-3-phosphorylcholineHMDB
1-HexadecanoyllysolecithinHMDB
1-Hexadecyl-sn-glycero-3-phosphocholineHMDB
1-O-Palmitoyl-2-lyso-sn-glycero-3-phosphocholineHMDB
1-O-Palmitoyl-sn-glycero-3-phosphocholineHMDB
1-O-Palmitoyl-sn-glyceryl-3-phosphorylcholineHMDB
1-Palmitoyl-2-lyso-sn-glycero-3-phosphocholineHMDB
1-Palmitoyl-L-alpha-lysophosphatidylcholineHMDB
1-Palmitoyl-L-α-lysophosphatidylcholineHMDB
1-Palmitoyl-sn-glycero-3-phosphorylcholineHMDB
1-Palmitoyl-sn-glycerol-3-phosphatidylcholineHMDB
1-Palmitoyl-sn-glycerol-3-phosphocholineHMDB
1-PalmitoyllecithinHMDB
C(16)-LysophosphatidylcholineHMDB
L-PalmitoyllysolecithinHMDB
L-alpha-LysopalmitoylphosphatidylcholineHMDB
L-alpha-PalmitoyllysophosphatidylcholineHMDB
L-Α-lysopalmitoylphosphatidylcholineHMDB
L-Α-palmitoyllysophosphatidylcholineHMDB
Lysophosphatidylcholine C16:0HMDB
MPPCHMDB
Palmitoyl L-alpha-lysolecithinHMDB
Palmitoyl L-alpha-lysophosphatidylcholineHMDB
Palmitoyl L-lysophosphatidylcholineHMDB
Palmitoyl L-α-lysolecithinHMDB
Palmitoyl L-α-lysophosphatidylcholineHMDB
gamma-Palmitoyl-L-alpha-lysophosphatidylcholineHMDB
Γ-palmitoyl-L-α-lysophosphatidylcholineHMDB
1-Hexadecanoyl-3-glycerophosphorylcholineHMDB
1-Palmitoyl-3-glycerylphosphorylcholineHMDB
1-PalmitoyllysolecithinHMDB
PalmitoyllysolecithinHMDB
Palmitoyllysophosphatidyl cholineHMDB
LysoPC(16:0/0:0)Lipid Annotator, ChEBI
Chemical FormulaC24H50NO7P
Average Molecular Weight495.6301
Monoisotopic Molecular Weight495.332489471
IUPAC Name(2-{[(2R)-3-(hexadecanoyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-(hexadecanoyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number17364-16-8
SMILES
CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C24H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h23,26H,5-22H2,1-4H3/t23-/m1/s1
InChI KeyASWBNKHCZGQVJV-HSZRJFAPSA-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

Adverse health effect

Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available233.3http://allccs.zhulab.cn/database/detail?ID=AllCCS00001990
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00037 g/LALOGPS
logP1.83ALOGPS
logP1.19ChemAxon
logS-6.2ALOGPS
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
Refractivity142.27 m³·mol⁻¹ChemAxon
Polarizability58.03 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+233.60230932474
DeepCCS[M-H]-231.24430932474
DeepCCS[M-2H]-264.47830932474
DeepCCS[M+Na]+240.98630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LysoPC(16:0/0:0)CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C3466.4Standard polar33892256
LysoPC(16:0/0:0)CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C3037.6Standard non polar33892256
LysoPC(16:0/0:0)CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C3330.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
LysoPC(16:0/0:0),1TMS,isomer #1CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C3308.9Semi standard non polar33892256
LysoPC(16:0/0:0),1TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C3538.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - LysoPC(16:0/0:0) GC-MS (1 TMS) - 70eV, Positivesplash10-01y9-9311000000-9632c8a0304eb91f37512017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - LysoPC(16:0/0:0) GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - LysoPC(16:0/0:0) GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) n/a 1V, negative-QTOFsplash10-001i-0010960000-db67de4509c75d7797d52020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) QTOF 10V, positive-QTOFsplash10-014i-0100190000-466a257c45e674564cc22020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) QTOF 15V, positive-QTOFsplash10-014i-0300490000-fd86cfc8580fd230b8a82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) QTOF 20V, positive-QTOFsplash10-1000-1900860000-1a2c5a54bd973898558d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) QTOF 30V, positive-QTOFsplash10-0zfr-2901600000-7c35aada431d2e8676522020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) QTOF 40V, positive-QTOFsplash10-0udi-5901100000-be073d1065c18511ab412020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) n/a 1V, positive-QTOFsplash10-0002-0300900000-849ef7d9847d865ee5422020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) QTOF 3V, positive-QTOFsplash10-0002-0000900000-bd89b3b43b9782d3e5d02020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) QTOF 4V, positive-QTOFsplash10-0002-0000900000-7c8338b951da28a32df82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) QTOF 5V, positive-QTOFsplash10-0002-0000900000-aa4c98d730731747150c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) QTOF 7V, positive-QTOFsplash10-0002-0000900000-2d0497b2b78955e2f3732020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) QTOF 10V, positive-QTOFsplash10-0002-0100900000-864a738c4e243f3650a82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) QTOF 15V, positive-QTOFsplash10-0002-0400900000-ce5450f53d5acc84a31e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) QTOF 17V, positive-QTOFsplash10-000t-0700900000-4ea431cd2258d012bb042020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) QTOF 20V, positive-QTOFsplash10-0f8a-0900400000-584dbb5e4958e61bcab82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) QTOF 23V, positive-QTOFsplash10-0f89-0900200000-2b522394881a967d30af2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) QTOF 25V, positive-QTOFsplash10-0f89-0900100000-64234f354a55048175bc2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) QTOF 27V, positive-QTOFsplash10-0f89-0900000000-5f827a15f6679c8604602020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) QTOF 30V, positive-QTOFsplash10-0f89-1900000000-f09c6fb5cf772c6435042020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) QTOF 33V, positive-QTOFsplash10-0f89-1900000000-d5bef12c7df660f031a92020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) QTOF 35V, positive-QTOFsplash10-0f89-1900000000-f069c0af6b2eb74b93362020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) QTOF 40V, positive-QTOFsplash10-0f89-3900000000-d43ab983a88913d219912020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) QTOF 45V, positive-QTOFsplash10-0f8i-5900000000-2b2fa2819f5e2fce5fe42020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) Orbitrap 13V, positive-QTOFsplash10-0002-0000900000-0b99348189a68c7f55922020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - LysoPC(16:0/0:0) Orbitrap 18V, positive-QTOFsplash10-0002-0300900000-4249906ba39f9c0a48ea2020-07-22HMDB team, MONAView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • All Tissues
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified141 +/- 50 uMAdult (>18 years old)Both
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified106.6 +/- 16.73 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified41.00-150.0 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified106.598 +/- 16.732 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified63.4 (53.2-76.6) uMNewborn (0-30 days old)Not Available
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified83.48(14.67) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified73.4 +/- 12.9 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified73.9 (58.5-96.1) uMInfant (0-1 year old)Not Available
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected and Quantified12.42 +/- 10.49 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified8.81 +/- 6.35 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.014 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0152 +/- 0.0103 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected and Quantified0.01-0.17 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified0.03(0.01-0.18) umol/mmol creatinineNewborn (0-30 days old)FemaleNormal details
UrineDetected and Quantified0.04(0.01-0.13) 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 Quantified12.7(1-30) uMAdult (>18 years old)BothSepsis details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Schizophrenia
details
BloodDetected and Quantified73.15(13.93) uMAdult (>18 years old)BothHeart failure with preserved ejection fraction details
BloodDetected and Quantified72.189 (66.133) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified142.065 (39.638) uMAdult (>18 years old)FemalePregnancy details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedLiver cirrhosis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specifiedhepatocellular carcinoma details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Bothliver cirrhosis details
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Not Specified
Premature neonates
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified0.0089 +/- 0.0053 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified0.0097 +/- 0.0084 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 ]
  2. Oresic M, Seppanen-Laakso T, Sun D, Tang J, Therman S, Viehman R, Mustonen U, van Erp TG, Hyotylainen T, Thompson P, Toga AW, Huttunen MO, Suvisaari J, Kaprio J, Lonnqvist J, Cannon TD: Phospholipids and insulin resistance in psychosis: a lipidomics study of twin pairs discordant for schizophrenia. Genome Med. 2012 Jan 18;4(1):1. doi: 10.1186/gm300. [PubMed:22257447 ]
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 ]
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. Cao H, Huang H, Xu W, Chen D, Yu J, Li J, Li L: Fecal metabolome profiling of liver cirrhosis and hepatocellular carcinoma patients by ultra performance liquid chromatography-mass spectrometry. Anal Chim Acta. 2011 Apr 8;691(1-2):68-75. doi: 10.1016/j.aca.2011.02.038. Epub 2011 Feb 23. [PubMed:21458633 ]
  2. 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 ]
Hepatocellular carcinoma
  1. Cao H, Huang H, Xu W, Chen D, Yu J, Li J, Li L: Fecal metabolome profiling of liver cirrhosis and hepatocellular carcinoma patients by ultra performance liquid chromatography-mass spectrometry. Anal Chim Acta. 2011 Apr 8;691(1-2):68-75. doi: 10.1016/j.aca.2011.02.038. Epub 2011 Feb 23. [PubMed:21458633 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
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 IDFDB027533
KNApSAcK IDNot Available
Chemspider ID405287
KEGG Compound IDC04230
BioCyc IDCPD-8343
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound460602
PDB IDNot Available
ChEBI ID72998
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000790
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 ]
  6. 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 ]
  7. Wernly B, Lichtenauer M, Hoppe UC, Jung C: Hyperglycemia in septic patients: an essential stress survival response in all, a robust marker for risk stratification in some, to be messed with in none. J Thorac Dis. 2016 Jul;8(7):E621-4. doi: 10.21037/jtd.2016.05.24. [PubMed:27501420 ]
  8. Knuplez E, Marsche G: An Updated Review of Pro- and Anti-Inflammatory Properties of Plasma Lysophosphatidylcholines in the Vascular System. Int J Mol Sci. 2020 Jun 24;21(12). pii: ijms21124501. doi: 10.3390/ijms21124501. [PubMed:32599910 ]
  9. Sun JK, Sun F, Wang X, Yuan ST, Zheng SY, Mu XW: Risk factors and prognosis of hypoalbuminemia in surgical septic patients. PeerJ. 2015 Oct 1;3:e1267. doi: 10.7717/peerj.1267. eCollection 2015. [PubMed:26557421 ]
  10. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  11. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

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.