Showing metabocard for LysoPC(P-16:0) (BMDB0010407)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:06:00 UTC
Update Date2020-05-11 19:11:27 UTC
BMDB IDBMDB0010407
Secondary Accession Numbers
  • BMDB10407
Metabolite Identification
Common NameLysoPC(P-16:0)
DescriptionLysoPC(P-16:0/0:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. LysoPC(P-16:0/0:0), in particular, consists of one 1Z-hexadecenyl chain. 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(20:3(5Z,8Z,11Z)), in particular, consists of one chain of mead acid at the C-1 position. The mead acid moiety is derived from fish oils, liver and kidney. 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(1-Enyl-palmitoyl)-glycero-3-phosphocholineChEBI
1-(1-Enyl-palmitoyl)-GPCChEBI
GPC(p-16:0)ChEBI
LPC p-16:0/0:0ChEBI
LPC(p-16:0/0:0)ChEBI
LysoPC p-16:0/0:0ChEBI
Lysophosphatidylcholine(p-16:0/0:0)ChEBI
PC p-16:0/0:0ChEBI
PC(p-16:0/0:0)ChEBI
LysoplasmalogensMeSH
LysoplasmenylcholineMeSH
LysoplasmenylethanolamineMeSH
LysoPC(P-16:0/0:0)ChEBI
Chemical FormulaC24H50NO6P
Average Molecular Weight479.6307
Monoisotopic Molecular Weight479.337574849
IUPAC Name(2-{[(2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-[(1Z)-hexadec-1-en-1-yloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCC\C=C/OC[C@](O)([H])COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C24H50NO6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-20-29-22-24(26)23-31-32(27,28)30-21-19-25(2,3)4/h18,20,24,26H,5-17,19,21-23H2,1-4H3/b20-18-/t24-/m1/s1
InChI KeyHTZINLFNXLXRBC-CQLBIITFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-(1z-alkenyl)-glycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one 1Z-alkenyl chain attached at the O1 position of a glycerol moiety through an ether linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-(1Z-alkenyl)-glycero-3-phosphocholines
Alternative Parents
Substituents
  • 1-(1z-alkenyl)-glycero-3-phosphocholine
  • Phosphocholine
  • Glycerol vinyl ether
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Secondary alcohol
  • Alcohol
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not 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
logP2.36ALOGPS
logP1.59ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area88.05 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity142.61 m³·mol⁻¹ChemAxon
Polarizability56.25 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 (Non-derivatized) - 70eV, Positivesplash10-008a-6930000000-2cd4d158d1da9483a0b8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0239-9310010000-7cb9ed0c647800289995View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-9161400000-acd172473da4e286d4f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ej-7490100000-79e2674f3d3635e27153View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0080-9240000000-5ec93db1ab0e3cff3be5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0062900000-d592b49af8e0a751ac82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-1194200000-1d423bdd4b255c190d9eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004r-7290000000-1ef3a8baf3e682029c1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0930500000-61a4014f908cb94de0cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-1320900000-88e62232177515252a1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01qc-1760900000-f92db205bdaf67b706b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-7040b29aa45cc5808d3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0020900000-583ecaabeb53f6779a7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9230000000-3b631f6658b951bdbde0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000090000-1d51aa2c190668184be4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0111910000-ff7b542a9c7e2f45b11aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03mi-0299920000-196c0c2456e22a4da048View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0010407
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112262
KNApSAcK IDNot Available
Chemspider ID9093054
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10917802
PDB IDNot Available
ChEBI ID73850
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available