Showing metabocard for LysoPC(18:3(6Z,9Z,12Z)) (BMDB0010387)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:05:36 UTC
Update Date2020-05-11 19:11:10 UTC
BMDB IDBMDB0010387
Secondary Accession Numbers
  • BMDB10387
Metabolite Identification
Common NameLysoPC(18:3(6Z,9Z,12Z))
DescriptionLysoPC(18:3(6Z,9Z,12Z)/0:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. LysoPC(18:3(6Z,9Z,12Z)/0:0), in particular, consists of one 6Z,9Z,12Z-octadecatrienoyl 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-g-Linolenoyl-glycero-3-phosphocholineHMDB
1-gamma-Linolenoyl-glycero-3-phosphocholineHMDB
LPC(18:3)HMDB
LPC(18:3/0:0)HMDB
LPC(18:3n6/0:0)HMDB
LPC(18:3W6/0:0)HMDB
LyPC(18:3)HMDB
LyPC(18:3/0:0)HMDB
LyPC(18:3n6/0:0)HMDB
LyPC(18:3W6/0:0)HMDB
LysoPC(18:3)HMDB
LysoPC(18:3/0:0)HMDB
LysoPC(18:3n6/0:0)HMDB
LysoPC(18:3W6/0:0)HMDB
Lysophosphatidylcholine(18:3)HMDB
Lysophosphatidylcholine(18:3/0:0)HMDB
Lysophosphatidylcholine(18:3n6/0:0)HMDB
Lysophosphatidylcholine(18:3W6/0:0)HMDB
LysoPC(18:3(6Z,9Z,12Z))HMDB
1-(6Z,9Z,12Z-Octadecatrienoyl)-glycero-3-phosphocholineHMDB
Chemical FormulaC26H48NO7P
Average Molecular Weight517.6356
Monoisotopic Molecular Weight517.316839407
IUPAC Name(2-{[(2R)-2-hydroxy-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-hydroxy-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/C\C=C/CCCCC(=O)OC[C@](O)([H])COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C26H48NO7P/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/h9-10,12-13,15-16,25,28H,5-8,11,14,17-24H2,1-4H3/b10-9-,13-12-,16-15-/t25-/m1/s1
InChI KeyMRTUWVDDQVMUCR-ACHCNROVSA-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
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
logP2.04ALOGPS
logP1ChemAxon
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 Count23ChemAxon
Refractivity154.83 m³·mol⁻¹ChemAxon
Polarizability57.71 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, Positivesplash10-03l3-9431010000-dc2fae56bd04819d152aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000090000-20dffa0496fc3ba6aebbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-0090070000-d5ab6b7a62a0456606feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0090020000-12fef0987b97e5dcd83aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000190000-d5d74be8ea8d7b5f4a6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01i0-0002990000-b6a9823678c3d88b82f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0frl-0309400000-dc557eebfc013a515d0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0000090000-34e22b7ec2dfa608c7d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-0900060000-d7c62d86e19a399eef99View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-0910040000-9aef0b06a99ef7cf7bbcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0030090000-ff94157d96b509c0c17fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1090010000-9dbf78ea53a727ac092eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1090000000-bee0f32ea6ed172745a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000190000-2b52d2700b0bcd6d1a23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0001960000-84838ee5cd4ae482bf66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pcr-1609710000-e5141f846c5e4a5a7f00View 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 IDHMDB0010387
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027538
KNApSAcK IDNot Available
Chemspider ID24766527
KEGG Compound IDC04230
BioCyc ID PHOSPHATIDYLCHOLINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52924045
PDB IDNot Available
ChEBI ID88698
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available