Showing metabocard for PC(15:0/18:1(9Z)) (BMDB0007939)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:47:31 UTC
Update Date2020-06-04 19:48:49 UTC
BMDB IDBMDB0007939
Secondary Accession Numbers
  • BMDB07939
Metabolite Identification
Common NamePC(15:0/18:1(9Z))
DescriptionPC(15:0/18:1(9Z)), also known as PC(15:0/18:1) or PC(33:1), 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(15:0/18:1(9Z)) is considered to be a glycerophosphocholine lipid molecule. PC(15:0/18:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(15:0/18:1(9Z)) exists in all eukaryotes, ranging from yeast to humans. PC(15:0/18:1(9Z)) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(15:0/18:1(9Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(15:0/18:1(9Z)) through the action of the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(15:0/18:1(9Z)) can be biosynthesized from CDP-choline and DG(15:0/18:1(9Z)/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PC(15:0/18:1(9Z)) and L-serine can be converted into choline and PS(15:0/18:1(9Z)); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(15:0/18:1(9Z)) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(15:0/18:1(9Z)) pathway and phosphatidylethanolamine biosynthesis pe(15:0/18:1(9Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Pentadecanoyl-2-(9Z-octadecenoyl)-glycero-3-phosphocholineHMDB
1-Pentadecanoyl-2-[(9Z)-octadecenoyl]-sn-glycero-3-phosphocholineHMDB
1-Pentadecanoyl-2-oleoyl-GPCHMDB
1-Pentadecanoyl-2-oleoyl-GPC (15:0/18:1)HMDB
GPC(15:0/18:1)HMDB
PC(15:0/18:1)HMDB
PC(15:0/18:1n9)HMDB
PC(15:0/18:1W9)HMDB
PC(33:1)HMDB
Phosphatidylcholine(15:0/18:1)HMDB
Phosphatidylcholine(15:0/18:1n9)HMDB
Phosphatidylcholine(15:0/18:1W9)HMDB
Phosphatidylcholine(33:1)HMDB
1-Pentadecanoyl-2-oleoyl-sn-glycero-3-phosphocholineHMDB
Gpcho(15:0/18:1)HMDB
Gpcho(15:0/18:1n9)HMDB
Gpcho(15:0/18:1W9)HMDB
Gpcho(33:1)HMDB
LecithinHMDB
1-Pentadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholineHMDB
PC(15:0/18:1(9Z))Lipid Annotator
Chemical FormulaC41H80NO8P
Average Molecular Weight746.0496
Monoisotopic Molecular Weight745.562155053
IUPAC Nametrimethyl(2-{[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(pentadecanoyloxy)propyl phosphonato]oxy}ethyl)azanium
Traditional Namelecithin
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C41H80NO8P/c1-6-8-10-12-14-16-18-20-21-22-24-26-28-30-32-34-41(44)50-39(38-49-51(45,46)48-36-35-42(3,4)5)37-47-40(43)33-31-29-27-25-23-19-17-15-13-11-9-7-2/h20-21,39H,6-19,22-38H2,1-5H3/b21-20-/t39-/m1/s1
InChI KeyZEWLMKXMNQOCOQ-KUNNKMQBSA-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
logP5.43ALOGPS
logP8.2ChemAxon
logS-7.5ALOGPS
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 Count40ChemAxon
Refractivity221.58 m³·mol⁻¹ChemAxon
Polarizability91.96 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, Positivesplash10-0isr-0000695200-5f1038942664ed664a4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000200-4a4aae1c56f0d82c90bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0190001000-c7f76117f70c236043edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0036-4190000000-121c7fcb82ea62260c47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000900-dea40d097d7939446bdbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000001900-e5028f86ed3b639928dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0i00-0100691100-51e54c79a2c72ac6d3c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000900-775208a25e34adb911eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0080042900-d5b94dd8133a2470de34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-1090100000-d15deeea9bbead7a02c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000000900-f838901a8cc5953bfd9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000000900-af19b0d392073b08857dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000j-0500390200-290208a30d762c099262View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000900-33c3132d5b9a740ac908View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-0600000900-348610127b1bcbb5a47dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900231200-e905fc1763966f86c3c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000000900-44b34785552db236c3b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0030000900-f336d6a4ef0e13237d72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-0090000400-b0a7cb6c0bb919583a5dView 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
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified1.45 +/- 0.04 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified2.2 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.1 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.92 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0007939
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025131
KNApSAcK IDNot Available
Chemspider ID24766614
KEGG Compound IDC00157
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52922312
PDB IDNot Available
ChEBI ID133623
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.