Showing metabocard for PC(18:0/18:0) (BMDB0008036)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:49:28 UTC
Update Date2020-06-04 20:02:11 UTC
BMDB IDBMDB0008036
Secondary Accession Numbers
  • BMDB08036
Metabolite Identification
Common NamePC(18:0/18:0)
DescriptionPC(18:0/18:0), also known as gpcho(36:0) or PC (18:0)2, 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(18:0/18:0) is considered to be a glycerophosphocholine lipid molecule. PC(18:0/18:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:0/18:0) exists in all eukaryotes, ranging from yeast to humans. PC(18:0/18:0) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(18:0/18:0) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:0/18:0); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(18:0/18:0) can be biosynthesized from CDP-choline and DG(18:0/18:0/0:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. Finally, PC(18:0/18:0) and L-serine can be converted into choline and PS(18:0/18:0); which is catalyzed by the enzyme phosphatidylserine synthase. In cattle, PC(18:0/18:0) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(18:0/18:0) pathway and phosphatidylethanolamine biosynthesis pe(18:0/18:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-Dioctadecanoyl-sn-glycero-3-phosphocholineChEBI
1,2-Distearoyl-sn-3-phosphacholineChEBI
Distearoyl phosphatidylcholineChEBI
GPC(18:0/18:0)ChEBI
GPCho(18:0/18:0)ChEBI
GPCho(36:0)ChEBI
PC (18:0)2ChEBI
PC 18:0/18:0ChEBI
PC(36:0)ChEBI
Phosphatidylcholine(18:0/18:0)ChEBI
Phosphatidylcholine(36:0)ChEBI
1,2-Distearoyl-sn-glycero-3-phosphocholineHMDB
1,2-Distearoyllecithin, (S)-isomerHMDB
1,2-Distearoyllecithin, (+-)-isomerHMDB
DistearoylglycerophosphocholineHMDB
1,2-DistearoyllecithinHMDB
DistearoylphosphatidylcholineHMDB
1,2-Distearoyllecithin, (R)-isomerHMDB
1,2-DistearoylphosphatidylcholineHMDB
1,2-Distearoyl-rac-glycero-3-phosphocholineHMDB
LecithinHMDB
1,2-Dioctadecanoyl-rac-glycero-3-phosphocholineHMDB
PC(18:0/18:0)Lipid Annotator
4-Hydroxy-N,N,N-trimethyl-10-oxo-7-((1-oxooctadecyl)oxy)-3,5,9-trioxa-4-phosphahepta cosan-1-aminium hydroxide, inner salt, 4-oxideMeSH
Chemical FormulaC44H88NO8P
Average Molecular Weight790.1452
Monoisotopic Molecular Weight789.624755309
IUPAC Name(2-{[(2R)-2,3-bis(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2,3-bis(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number816-94-4
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C44H88NO8P/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/h42H,6-41H2,1-5H3/t42-/m1/s1
InChI KeyNRJAVPSFFCBXDT-HUESYALOSA-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
logP5.92ALOGPS
logP9.89ChemAxon
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 Count44ChemAxon
Refractivity234.27 m³·mol⁻¹ChemAxon
Polarizability99.02 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 31V, negativesplash10-0089-0000000590-0aad18afe34a7c3e4d4cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 39V, negativesplash10-00e9-0000000950-0e01653ba450f4cf2474View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 45V, negativesplash10-00e9-0030000910-5f5f6ea7c69c11446a37View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 52V, negativesplash10-0089-0090000600-450dc346ec045426f41aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 58V, negativesplash10-001i-0090000200-ac0ebb03ecad4a755352View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 64V, negativesplash10-001i-0090000000-0cda3c7a3fd1efdab660View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 78V, negativesplash10-001i-0090000000-8039839adbbb06bce8ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 97V, negativesplash10-001i-0090000000-32180842465e1f0ca062View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 118V, negativesplash10-001i-0090000000-add4cfd543c3c7500150View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 143V, negativesplash10-001i-1090000000-731977fa0efe340b2c9bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 170V, negativesplash10-003r-6090000000-10e012ff7fe106b8a5f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 210V, negativesplash10-004i-9000000000-003f91760dbf6d21ebe7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 55V, negativesplash10-00di-0000000900-ed2638f28be0dc446783View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 22V, positivesplash10-0006-0000000900-08c46febfbe4ee762593View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 34V, positivesplash10-000x-0600000900-f13e1162895079b39581View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 48V, positivesplash10-001i-0900000000-095cbcd6f3947470459dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 74V, positivesplash10-001i-0900000000-b0b68022ed94da51246cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 99V, positivesplash10-001i-2900000000-552209425d26c02a0476View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 124V, positivesplash10-008i-6900000000-b39bf3dd8da792e30123View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 161V, positivesplash10-0079-9600000000-6622c8393c18efd1dd28View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 198V, positivesplash10-007a-9400000000-a1be01e41d76c34ddef8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 236V, positivesplash10-0072-9200000000-df8e8bf2dc44c5e36e28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000000900-ddeff1f077816b130f0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-0600000900-cbf5b5700da15bd27fafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900021300-9f90c5ee485e939b0d38View 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
  • Blood
  • Liver
  • Longissimus Thoracis Muscle
  • Milk
  • Ruminal Fluid
  • Semimembranosus Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
BloodDetected and Quantified6 +/- 2 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
LiverDetected and Quantified17 +/- 5 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Longissimus Thoracis MuscleDetected and Quantified0.85 +/- 0.14 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
MilkDetected and Quantified0.66 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.74 +/- 0.01 uMNot SpecifiedNot Specified
Normal		 details
Ruminal FluidDetected and Quantified0.07 +/- 0.04 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Semimembranosus MuscleDetected and Quantified1 +/- 0.2 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
TestisDetected and Quantified15 +/- 3 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0008036
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025227
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound94190
PDB IDNot Available
ChEBI ID83718
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(18:0/18:0) + L-Serine → Choline + PS(18:0/18:0)details