Showing metabocard for LysoPC(22:1(13Z)) (BMDB0010399)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:05:51 UTC
Update Date2020-05-11 19:11:20 UTC
BMDB IDBMDB0010399
Secondary Accession Numbers
  • BMDB10399
Metabolite Identification
Common NameLysoPC(22:1(13Z))
DescriptionLysoPC(22:1(13Z)/0:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. LysoPC(22:1(13Z)/0:0), in particular, consists of one 13Z-docosenoyl 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-Erucoyl-glycero-3-phosphocholineHMDB
LPC(22:1)HMDB
LPC(22:1/0:0)HMDB
LPC(22:1n9/0:0)HMDB
LPC(22:1W9/0:0)HMDB
LyPC(22:1)HMDB
LyPC(22:1/0:0)HMDB
LyPC(22:1n9/0:0)HMDB
LyPC(22:1W9/0:0)HMDB
LysoPC(22:1)HMDB
LysoPC(22:1/0:0)HMDB
LysoPC(22:1n9/0:0)HMDB
LysoPC(22:1W9/0:0)HMDB
Lysophosphatidylcholine(22:1)HMDB
Lysophosphatidylcholine(22:1/0:0)HMDB
Lysophosphatidylcholine(22:1n9/0:0)HMDB
Lysophosphatidylcholine(22:1W9/0:0)HMDB
LysoPC(22:1(13Z))HMDB
1-(13Z-Docosenoyl)-glycero-3-phosphocholineHMDB
1-ErucoylglycerophosphocholineHMDB
Chemical FormulaC30H60NO7P
Average Molecular Weight577.7737
Monoisotopic Molecular Weight577.410739791
IUPAC Name(2-{[(2R)-3-[(13Z)-docos-13-enoyloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-[(13Z)-docos-13-enoyloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/CCCCCCCCCCCC(=O)OC[C@@]([H])(O)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C30H60NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-30(33)36-27-29(32)28-38-39(34,35)37-26-25-31(2,3)4/h12-13,29,32H,5-11,14-28H2,1-4H3/b13-12-/t29-/m1/s1
InChI KeyPAFOXYLFALKPOE-BKAVPCLVSA-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 DescriptorsNot Available
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
logP3.56ALOGPS
logP3.5ChemAxon
logS-6.9ALOGPS
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 Count29ChemAxon
Refractivity171 m³·mol⁻¹ChemAxon
Polarizability69.2 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, Positivesplash10-00ed-5941200000-ea619fcb42166e0fa399View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0233-9412001000-2227b2f287aa1e70b51cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("LysoPC(22:1(13Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9126030000-41dc72c796ec37851780View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00du-9348010000-cf9a7745c2ae81ec6d9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05a9-9023000000-f6fcc434144367501ea6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00n0-0009140000-c9000b41fb63caba7c01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0009100000-60ea12545ec113640b78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00n0-5119000000-2bbce4ac121a8cefb18aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000090000-39eedd6e51bddec63dfaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0060-0001090000-0f06ab57848f4e9e59a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufs-1609770000-19f90f55cfc358341f17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000039000-285f86ddfb76289458e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01p9-0009016000-0bba2b894f93dc35cf89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0039011000-31c0eee870a88e98003cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0003090000-c7d44a75da892d1b4fa1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1009010000-7e385a98f41f434c2c89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0009000000-36b8b1e7caa291bed45aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000019000-cfa91d32327681c1b9bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6x-0001096000-365b66832ac4c117c1ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbf-1701981000-f9bdd10f4c97717d33d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0000090000-a29d6a14d513c0d92105View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003r-0900060000-48abe3418040067dbcc1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gx0-0910040000-18a0e9683d2b54e2ca58View 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 IDHMDB0010399
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027550
KNApSAcK IDNot Available
Chemspider ID24766534
KEGG Compound IDC04230
BioCyc ID PHOSPHATIDYLCHOLINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480471
PDB IDNot Available
ChEBI ID88684
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available