Showing Compound Card for LysoPC(18:2(9Z,12Z)/0:0) (CDB006341)

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Record Information
Version1.0
Created at2020-09-11 15:49:42 UTC
Updated at2022-12-13 23:36:29 UTC
CannabisDB IDCDB006341
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameLysoPC(18:2(9Z,12Z)/0:0)
DescriptionLysoPC(18:2(9Z,12Z)/0:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. LysoPC(18:2(9Z,12Z)/0:0), in particular, consists of one 9Z,12Z-octadecadienoyl 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-(9Z,12Z)-Octadecadienoyl-sn-glycero-3-phosphocholineChEBI
1-(9Z,12Z-Octadecadienoyl)-glycero-3-phosphocholineChEBI
1-(9Z,12Z-Octadecadienoyl)-sn-glycero-3-phosphocholineChEBI
1-18:2-LysoPCChEBI
1-Linoleoyl-glycero-3-phosphocholineChEBI
1-Linoleoyl-GPCChEBI
1-Linoleoyl-GPC (18:2)ChEBI
1-LinoleoylglycerophosphocholineChEBI
GPC(18:2)ChEBI
GPC(18:2/0:0)ChEBI
LPC 18:2(9Z,12Z)/0:0ChEBI
LPC(18:2)ChEBI
LPC(18:2/0:0)ChEBI
LPC(18:2n6/0:0)ChEBI
LPC(18:2Omega6/0:0)ChEBI
LyPC(18:2)ChEBI
LyPC(18:2n6/0:0)ChEBI
LyPC(18:2omega6/0:0)ChEBI
LysoPC 18:2(9Z,12Z)/0:0ChEBI
LysoPC(18:2)ChEBI
LysoPC(18:2/0:0)ChEBI
LysoPC(18:2n6/0:0)ChEBI
LysoPC(18:2omega6/0:0)ChEBI
Lysophosphatidylcholine(18:2(9Z,12Z)/0:0)ChEBI
Lysophosphatidylcholine(18:2)ChEBI
Lysophosphatidylcholine(18:2/0:0)ChEBI
Lysophosphatidylcholine(18:2n6/0:0)ChEBI
Lysophosphatidylcholine(18:2omega6/0:0)ChEBI
PC 18:2(9Z,12Z)/0:0ChEBI
PC(18:2(9Z,12Z)/0:0)ChEBI
LyPC(18:2/0:0)HMDB
LysoPC(18:2(9Z,12Z))HMDB
1-Linoleoyl lysolecithinHMDB
1-Linoleoyl-sn-glycero-3-phosphorylcholineHMDB
1-Linoleoylglycerol-3-phosphorylcholineHMDB
1-LinoleoylphosphatidylcholineHMDB
LinoleoyllysolecithinHMDB
Linoleyl lysophosphatidylcholineHMDB
Lysophosphatidylcholine 18:2HMDB
1-Linoleoyl-lysophosphatidylcholineHMDB
1-Linoleoyl-sn-glycero-3-phosphocholineHMDB
GPC(18:2(9Z,12Z))HMDB
GPC(18:2(9Z,12Z)/0:0)HMDB
GPC(18:2n6)HMDB
GPC(18:2n6/0:0)HMDB
GPC(18:2W6)HMDB
GPC(18:2W6/0:0)HMDB
LPC(18:2(9Z,12Z))HMDB
LPC(18:2(9Z,12Z)/0:0)HMDB
LPC(18:2n6)HMDB
LPC(18:2W6)HMDB
LPC(18:2W6/0:0)HMDB
LysoPC(18:2n6)HMDB
LysoPC(18:2W6)HMDB
LysoPC(18:2W6/0:0)HMDB
Lysophosphatidylcholine(18:2(9Z,12Z))HMDB
Lysophosphatidylcholine(18:2n6)HMDB
Lysophosphatidylcholine(18:2W6)HMDB
Lysophosphatidylcholine(18:2W6/0:0)HMDB
LysoPC(18:2(9Z,12Z)/0:0)ChEBI
Chemical FormulaC26H50NO7P
Average Molecular Weight519.6515
Monoisotopic Molecular Weight519.332489471
IUPAC Name(2-{[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C26H50NO7P/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/h9-10,12-13,25,28H,5-8,11,14-24H2,1-4H3/b10-9-,13-12-/t25-/m1/s1
InChI KeySPJFYYJXNPEZDW-FTJOPAKQSA-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
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.22ALOGPS
logP1.36ChemAxon
logS-6.3ALOGPS
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
Refractivity153.71 m³·mol⁻¹ChemAxon
Polarizability58.75 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLysoPC(18:2(9Z,12Z)/0:0), 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03kl-9431010000-c20360afbdedc9d9232fSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000190000-3c86eb832bb0e5b457ff2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0190-0002990000-61bb2de3bf360b7c57842021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0frl-0309400000-703f583c1dec34d853632021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0000090000-971f1431e3c2228b9f5d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-0900060000-dd4dca9634d21e863fe42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-0910040000-75b3d9cd99357a6300432021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0030090000-9b4f9f161f1e634d70b62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1090010000-2378656ce1b1501e42df2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1090000000-ed0e0c463537d6bd8f932021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000190000-85bff21ad2f9c91a74472021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001l-0001960000-38c8f8d665d29a3102862021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pcr-1609710000-e08a75389116b197e7742021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000090000-7d81a037787f63d958552021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-0090070000-6e0343e152dc3c713a982021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0090020000-20568d21d5462d55a6c02021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.00466 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.0112 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.00549 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.00465 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.0136 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.00599 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0010386
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030316
KNApSAcK IDNot Available
Chemspider ID9181014
KEGG Compound IDNot Available
BioCyc IDCPD-8347
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11005824
PDB IDNot Available
ChEBI ID28733
References
General ReferencesNot Available