Showing metabocard for LysoPC(18:1(9Z)/0:0) (BMDB0002815)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:01:40 UTC
Update Date2020-06-04 20:06:10 UTC
BMDB IDBMDB0002815
Secondary Accession Numbers
  • BMDB0062748
  • BMDB02815
  • BMDB62748
Metabolite Identification
Common NameLysoPC(18:1(9Z)/0:0)
DescriptionPC(18:1(9Z)/0:0), also known as lysopc 18:1(9Z)/0:0 or LPC(18:1W9/0:0), 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(18:1(9Z)/0:0) is considered to be a glycerophosphocholine lipid molecule. PC(18:1(9Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:1(9Z)/0:0) exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(9Z-Octadecenoyl)-sn-glycero-3-phosphocholineChEBI
1-Oleoyl-2-hydroxy-sn-glycero-3-phosphocholineChEBI
1-Oleoyl-sn-glycero-3-phosphorylcholineChEBI
1-OleoylglycerophosphocholineChEBI
3-Oleoyl-rac-glycerol-1-phosphorylcholineChEBI
a 1-(9Z-Octadecenoyl)-sn-glycero-3-phosphocholineChEBI
LPC 18:1ChEBI
LPC 18:1(9Z)/0:0ChEBI
LPC(18:1(9Z)/0:0)ChEBI
LysoPC 18:1(9Z)/0:0ChEBI
Lysophosphatidylcholine 18:1ChEBI
Lysophosphatidylcholine(18:1(9Z)/0:0)ChEBI
PC 18:1(9Z)/0:0ChEBI
PC(18:1(9Z)/0:0)ChEBI
1-Oleoyl-glycero-3-phosphocholineHMDB
LysoPC(18:1/0:0)HMDB
LysoPC(18:1(9Z))HMDB
Lysophosphatidylcholine(18:1)HMDB
LysoPC(18:1)HMDB
LyPC(18:1/0:0)HMDB
LyPC(18:1)HMDB
LPC(18:1/0:0)HMDB
LPC(18:1)HMDB
1-(9Z-Octadecenoyl)-glycero-3-phosphocholineHMDB
Lysophosphatidylcholine(18:1/0:0)HMDB
1-(9Z)-Octadecenoyl-sn-glycero-3-phosphocholineHMDB
1-Oleoyl-sn-glycero-3-phosphocholineHMDB
Choline phosphate (ester) 3-ester with 1-monooleinHMDB
Choline phosphate 3-ester with 1-monooleinHMDB
Gpcho(18:1(9Z)/0:0)[rac]HMDB
LPC(18:1n9/0:0)HMDB
LPC(18:1W9/0:0)HMDB
LyPC(18:1W9/0:0)HMDB
LysoPC a C18:1HMDB
LysoPC(18:1n9/0:0)HMDB
LysoPC(18:1W9/0:0)HMDB
Lysophosphatidylcholine(18:1n9/0:0)HMDB
Lysophosphatidylcholine(18:1W9/0:0)HMDB
LysoPIC(18:1/0:0)HMDB
Olein-1-mono-3-phosphate ester with cholineHMDB
Oleoyl lysolecithinHMDB
Oleoyl lysophosphatidylcholineHMDB
1-(cis-9-Octadecenoyl)-sn-glycero-3-phosphocholineHMDB
1-OGPCHMDB
1-Oleoyl lysophosphatidylcholineHMDB
1-Oleoyl-lysopcHMDB
1-O-Oleoyl-sn-glycero-3-phosphocholineHMDB
1-Oleoyl-2-hydroxy-sn-glycerol-3-phosphocholineHMDB
1-Oleoyl-GPCHMDB
1-Oleoyl-lysophosphatidylcholineHMDB
1-Oleoyl-sn-glycerol-3-phosphatidylcholineHMDB
1-Oleoyl-sn-glycerol-3-phosphorylcholineHMDB
GPC(18:1(9Z))HMDB
GPC(18:1(9Z)/0:0)HMDB
GPC(18:1)HMDB
GPC(18:1n9)HMDB
GPC(18:1n9/0:0)HMDB
GPC(18:1W9)HMDB
GPC(18:1W9/0:0)HMDB
LPC(18:1(9Z))HMDB
LPC(18:1n9)HMDB
LPC(18:1W9)HMDB
LysoPC(18:1n9)HMDB
LysoPC(18:1W9)HMDB
Lysophosphatidylcholine C18:1HMDB
Lysophosphatidylcholine(18:1(9Z))HMDB
Lysophosphatidylcholine(18:1n9)HMDB
Lysophosphatidylcholine(18:1W9)HMDB
LysoPC(18:1(9Z)/0:0)ChEBI
Chemical FormulaC26H52NO7P
Average Molecular Weight521.6673
Monoisotopic Molecular Weight521.348139535
IUPAC Name(2-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number3542-29-8
SMILES
[H][C@@](O)(COC(=O)CCCCCCC\C=C/CCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C26H52NO7P/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/h12-13,25,28H,5-11,14-24H2,1-4H3/b13-12-/t25-/m1/s1
InChI KeyYAMUFBLWGFFICM-PTGWMXDISA-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
logP2.38ALOGPS
logP1.72ChemAxon
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 Count25ChemAxon
Refractivity152.59 m³·mol⁻¹ChemAxon
Polarizability60.02 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, Positivesplash10-024u-9431010000-8c34065bb1a9ce8460a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0030090000-c08a294df5c170ac8b76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1090010000-3f3fbc869926a73a5b72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0090000000-1894b105723e28dacec8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0000090000-382efaabb1329b98f1aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0089-0900060000-7d4d5ee776e7a08537aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-0910040000-b15364334c9b09b73db5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000190000-ed1ce66db5beed8bfab7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-0001960000-b2d5105862a37356da93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gw0-1609710000-4adbedbb1f89568d7285View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000090000-f6a072a97b578a3bd0b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-0090070000-f56fc89aebf13639f1aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0090020000-be75beb7bf742731dc1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000190000-37dcc74901c1425d0392View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0190-0002990000-c8110d0a5e4476020596View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0frj-0309400000-cd464845573077fb0e9fView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • Blood
  • Liver
  • Longissimus Thoracis Muscle
  • Milk
  • Placenta
  • Ruminal Fluid
  • Semimembranosus Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified6 +/- 1 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
BloodDetected and Quantified18-69 uMNot SpecifiedNot Specified
Normal		 details
LiverDetected and Quantified0.87 +/- 0.23 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Longissimus Thoracis MuscleDetected and Quantified0.3 +/- 0.1 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
MilkDetected and Quantified0.366 +/- 0.002 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.366 +/- 0.004 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.47 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.481 +/- 0.004 uMNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Ruminal FluidDetected and Quantified0.074 +/- 0.051 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Ruminal FluidDetected and Quantified0.14 +/- 0.04 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Semimembranosus MuscleDetected and Quantified0.4 +/- 0.1 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
TestisDetected and Quantified0.4 +/- 0.1 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0002815
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB005287
KNApSAcK IDNot Available
Chemspider ID17240641
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16081932
PDB IDNot Available
ChEBI ID28610
References
Synthesis ReferenceChung, Guk Hoon; Kim, Sun Ki; Rhee, Joon Shick; Han, Jeong Joon. Process for preparing lysophospholipids using enzymes. U.S. (2001), 8 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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.