Showing metabocard for PC(18:0/18:1(9Z)) (BMDB0008038)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:49:30 UTC
Update Date2020-06-04 19:57:48 UTC
BMDB IDBMDB0008038
Secondary Accession Numbers
  • BMDB08038
Metabolite Identification
Common NamePC(18:0/18:1(9Z))
DescriptionPC(18:0/18:1(9Z)), also known as sopc or GPC(18:0/18:1), belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage. Thus, PC(18:0/18:1(9Z)) is considered to be a glycerophosphocholine lipid molecule. PC(18:0/18:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:0/18:1(9Z)) exists in all eukaryotes, ranging from yeast to humans. PC(18:0/18:1(9Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:0/18:1(9Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:0/18:1(9Z)); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. In addition, Cytidine monophosphate and PC(18:0/18:1(9Z)) can be biosynthesized from CDP-choline and DG(18:0/18:1(9Z)/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. In cattle, PC(18:0/18:1(9Z)) is involved in the metabolic pathway called phosphatidylcholine biosynthesis PC(18:0/18:1(9Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R)-3-(Octadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propyl 2-(trimethylammonio)ethyl phosphateChEBI
1-18:0-2-18:1-PhosphatidylcholineChEBI
1-Octadecanoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholineChEBI
1-Octadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholineChEBI
1-Stearoyl-2-oleoyl-GPCChEBI
1-Stearoyl-2-oleoyl-GPC (18:0/18:1)ChEBI
1-Steroyl-2-oleoylphosphatidylcholineChEBI
18:0-18:1-PCChEBI
GPC(18:0/18:1)ChEBI
GPCho 18:0/18:1(9Z)ChEBI
L-alpha-1-Stearoyl-2-oleoyl lecithinChEBI
PC 18:0/18:1(9Z)ChEBI
PC(18:0/18:1n9)ChEBI
PC(18:0/18:1omega9)ChEBI
PC(18:0/18:1W9)ChEBI
Phosphatidylcholine(18:0/18:1(9Z))ChEBI
Phosphatidylcholine(18:0/18:1)ChEBI
Phosphatidylcholine(18:0/18:1n9)ChEBI
Phosphatidylcholine(18:0/18:1omega9)ChEBI
Phosphatidylcholine(18:0/18:1W9)ChEBI
Phosphatidylcholine(36:1)ChEBI
SOPCChEBI
(2R)-3-(Octadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propyl 2-(trimethylammonio)ethyl phosphoric acidGenerator
L-a-1-Stearoyl-2-oleoyl lecithinGenerator
L-Α-1-stearoyl-2-oleoyl lecithinGenerator
GPCho(36:1)Lipid Annotator, HMDB
PC(36:1)Lipid Annotator, HMDB
1-stearoyl-2-oleoyl-sn-glycero-3-phosphocholineLipid Annotator, MeSH, HMDB
PC(18:0/18:1)Lipid Annotator, HMDB
LecithinLipid Annotator, HMDB
PC(18:0/18:1(9Z))Lipid Annotator
GPCho(18:0/18:1)Lipid Annotator, HMDB
1-Stearoyl-2-oleoyl-sn-glycero-3-phosphocholine, (e)-isomerMeSH, HMDB
1-Stearoyl-2-oleoyl-sn-glycero-3-phosphocholine, (S-(Z))-isomerMeSH, HMDB
1-Stearoyl-2-oleoyl lecithinMeSH, HMDB
1-Stearoyl-2-oleoyl-sn-glycero-3-phosphocholine, (R-(Z))-isomerMeSH, HMDB
1-SOPCMeSH, HMDB
1-Stearoyl-2-oleoyl-sn-3-glycerophosphocholineMeSH, HMDB
1-Stearoyl-2-oleoyl glycerylphosphorylcholineHMDB
1-Stearoyl-2-oleoyl-sn-glycero-phosphatidylcholineHMDB
1-Stearoyl-2-oleoyllecithinHMDB
1-Stearoyl-2-oleoylphosphatidylcholineHMDB
1-Stearyl-2-oleoyl-3-sn-glycerophosphatidylcholineHMDB
GPC(18:0/18:1(9Z))HMDB
GPC(18:0/18:1n9)HMDB
GPC(18:0/18:1w9)HMDB
GPC(36:1)HMDB
GPCho(18:0/18:1(9Z))HMDB
GPCho(18:0/18:1n9)HMDB
GPCho(18:0/18:1w9)HMDB
L-alpha-1-Stearoyl-2-oleoylphosphatidylcholineHMDB
L-α-1-Stearoyl-2-oleoylphosphatidylcholineHMDB
Chemical FormulaC44H86NO8P
Average Molecular Weight788.1293
Monoisotopic Molecular Weight787.609105245
IUPAC Nametrimethyl(2-{[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(octadecanoyloxy)propyl phosphono]oxy}ethyl)azanium
Traditional Nametrimethyl(2-{[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(octadecanoyloxy)propyl phosphono]oxy}ethyl)azanium
CAS Registry Number6753-56-6
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C44H86NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h21,23,42H,6-20,22,24-41H2,1-5H3/b23-21-/t42-/m1/s1
InChI KeyATHVAWFAEPLPPQ-VRDBWYNSSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentPhosphatidylcholines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic salt
  • 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
logP5.89ALOGPS
logP9.53ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area111.19 ŲChemAxon
Rotatable Bond Count43ChemAxon
Refractivity235.39 m³·mol⁻¹ChemAxon
Polarizability97.79 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000900-b859f2c3b3c1a8178429View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-0600000900-740e271e86363b8b605aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900041300-22e6346bd3881ccf6ad0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-5649a580e0942e999145View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000000190-fad619901ff8ea0e25d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-0900369110-8d8283d716b8945882e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000090-c7d2a706ee4c08cac004View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0030000090-9becebc4c350016d45deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0089-0090000040-58b0dfd010ce87ff0a8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000900-11c57723ac725e930e50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0019-0071010900-5a423108e9ed5868292aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2092200000-f53135f214f9fe93df45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000900-575f764ae3b8a734c007View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-0600000900-1e34e2e526af2e3adedaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0089-1900041300-20b479e3bfdf095f4186View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000900-973b6e2c5af7633f95b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000000900-7a868a8ad9eb6f9e7bbdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0200498400-d8a93635e28c18a04dd4View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Milk
  • Placenta
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified5.46 +/- 0.02 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified6.5 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified8.6 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified5.23 +/- 0.03 uMNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Ruminal FluidDetected and Quantified0.157 +/- 0.135 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008038
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24766704
KEGG Compound IDNot Available
BioCyc IDCPD-8278
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24778825
PDB IDNot Available
ChEBI ID75034
References
Synthesis ReferenceNot Available
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.

Enzymes

Enzyme Details
1. Phosphatidylserine synthase 1
General function:
Not Available
Specific function:
Catalyzes a base-exchange reaction in which the polar head group of phosphatidylethanolamine (PE) or phosphatidylcholine (PC) is replaced by L-serine. In membranes, PTDSS1 catalyzes mainly the conversion of phosphatidylcholine. Also converts, in vitro and to a lesser extent, phosphatidylethanolamine (By similarity).
Gene Name:
PTDSS1
Uniprot ID:
Q2KHY9
Molecular weight:
55416.0
Reactions
PC(18:0/18:1(9Z)) + L-Serine → Choline + PS(18:0/18:1(9Z))details