Showing metabocard for LysoPC(16:0/0:0) (BMDB0010382)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:05:30 UTC
Update Date2020-06-04 20:05:04 UTC
BMDB IDBMDB0010382
Secondary Accession Numbers
  • BMDB0062711
  • BMDB10382
  • BMDB62711
Metabolite Identification
Common NameLysoPC(16:0/0:0)
DescriptionPC(16:0/0:0), also known as 16:0 lyso-PC or 1-palmitoyl-GPC, 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. Thus, PC(16:0/0:0) is considered to be a glycerophosphocholine lipid molecule. PC(16:0/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:0/0:0) exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Number14863-27-5
SMILES
[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCC)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
StatusDetected and 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
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01y9-9311000000-9632c8a0304eb91f3751View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - n/a 1V, negativesplash10-001i-0010960000-db67de4509c75d7797d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-014i-0100190000-466a257c45e674564cc2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-014i-0300490000-fd86cfc8580fd230b8a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-1000-1900860000-1a2c5a54bd973898558dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-0zfr-2901600000-7c35aada431d2e867652View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-0udi-5901100000-be073d1065c18511ab41View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 1V, positivesplash10-0002-0300900000-849ef7d9847d865ee542View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 3V, positivesplash10-0002-0000900000-bd89b3b43b9782d3e5d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-0002-0000900000-7c8338b951da28a32df8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-0002-0000900000-aa4c98d730731747150cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-0002-0000900000-2d0497b2b78955e2f373View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-0002-0100900000-864a738c4e243f3650a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-0002-0400900000-ce5450f53d5acc84a31eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-000t-0700900000-4ea431cd2258d012bb04View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-0f8a-0900400000-584dbb5e4958e61bcab8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-0f89-0900200000-2b522394881a967d30afView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-0f89-0900100000-64234f354a55048175bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-0f89-0900000000-5f827a15f6679c860460View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-0f89-1900000000-f09c6fb5cf772c643504View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-0f89-1900000000-d5bef12c7df660f031a9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-0f89-1900000000-f069c0af6b2eb74b9336View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-0f89-3900000000-d43ab983a88913d21991View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 45V, positivesplash10-0f8i-5900000000-2b2fa2819f5e2fce5fe4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-0002-0000900000-0b99348189a68c7f5592View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 18V, positivesplash10-0002-0300900000-4249906ba39f9c0a48eaView in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Blood
  • Liver
  • Longissimus Thoracis Muscle
  • Milk
  • Placenta
  • Ruminal Fluid
  • Semimembranosus Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
BloodDetected and Quantified15-58 uMNot SpecifiedNot Specified
Normal		 details
BloodDetected and Quantified20 +/- 4 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
LiverDetected and Quantified0.7 +/- 0.2 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Longissimus Thoracis MuscleDetected and Quantified0.1 +/- 0.02 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
MilkDetected and Quantified1.00 +/- 0.04 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.97 +/- 0.03 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.20 +/- 0.03 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified1.25 +/- 0.02 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Ruminal FluidDetected and Quantified0.03 +/- 0.018 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.02 +/- 0.019 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.03 +/- 0.02 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.14 +/- 0.02 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.14 +/- 0.02 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Ruminal FluidDetected and Quantified0.3 +/- 0.2 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Semimembranosus MuscleDetected and Quantified0.11 +/- 0.03 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
TestisDetected and Quantified0.7 +/- 0.1 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0010382
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]
  2. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

Enzyme Details
1. Acyl-protein thioesterase 1
General function:
Involved in hydrolase activity
Specific function:
Acts as a acyl-protein thioesterase hydrolyzing fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS (By similarity). Has depalmitoylating activity toward KCNMA1 (By similarity). Acts as a lysophospholipase hydrolyzing various lysophospholipids including lysophosphatidylcholine (lyso-PC), lysophosphatidylethanolamine (lyso-PE), lysophosphatidylinositol (lyso-PI) and lysophosphatidylserine (lyso-PS) (By similarity). Has much higher thioesterase activity than lysophospholipase activity (By similarity). Contributes to the production of lysophosphatidic acid (LPA) during blood coagulation by recognizing and cleaving plasma phospholipids to generate lysophospholipids which in turn act as substrates for ENPP2 to produce LPA (By similarity).
Gene Name:
LYPLA1
Uniprot ID:
Q3MHR0
Molecular weight:
24596.0
Reactions
LysoPC(16:0/0:0) → Citicolinedetails
Enzyme Details
2. Phospholipase A2, membrane associated
General function:
Not Available
Specific function:
Catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Thought to participate in the regulation of phospholipid metabolism in biomembranes including eicosanoid biosynthesis. Independent of its catalytic activity, acts as a ligand for integrins. Binds to and activates integrins ITGAV:ITGB3, ITGA4:ITGB1 and ITGA5:ITGB1. Binds to a site (site 2) which is distinct from the classical ligand-binding site (site 1) and induces integrin conformational changes and enhanced ligand binding to site 1. Induces cell proliferation in an integrin-dependent manner.
Gene Name:
PLA2G2A
Uniprot ID:
Q56JZ2
Molecular weight:
16347.0
Reactions
PC(16:0/16:0) → LysoPC(16:0/0:0)details