Showing metabocard for PC(14:0/16:0) (BMDB0007869)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:46:04 UTC
Update Date2020-06-04 19:55:25 UTC
BMDB IDBMDB0007869
Secondary Accession Numbers
  • BMDB07869
Metabolite Identification
Common NamePC(14:0/16:0)
DescriptionPC(14:0/16:0), also known as MPPC or PC(30:0), 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(14:0/16:0) is considered to be a glycerophosphocholine lipid molecule. PC(14:0/16:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(14:0/16:0) exists in all eukaryotes, ranging from yeast to humans. PC(14:0/16:0) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(14:0/16:0) can be biosynthesized from S-adenosylmethionine and pe-nme2(14:0/16:0); which is mediated by the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(14:0/16:0) can be biosynthesized from CDP-choline and DG(14:0/16:0/0:0) through the action of the enzyme choline/ethanolaminephosphotransferase. Finally, PC(14:0/16:0) and L-serine can be converted into choline and PS(14:0/16:0); which is mediated by the enzyme phosphatidylserine synthase. In cattle, PC(14:0/16:0) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(14:0/16:0) pathway and phosphatidylethanolamine biosynthesis pe(14:0/16:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Myristoyl-2-palmitoyl-GPCChEBI
1-Myristoyl-2-palmitoyl-GPC (14:0/16:0)ChEBI
1-Myristoyl-2-palmitoylphosphatidylcholineChEBI
1-Tetradecanoyl-2-hexadecanoyl-sn-glycero-3-phosphocholineChEBI
1-Tetradecanoyl-2-hexadecanoylphosphatidylcholineChEBI
GPC(14:0/16:0)ChEBI
MPPCChEBI
PC(30:0)ChEBI
Phosphatidylcholine(14:0/16:0)ChEBI
Phosphatidylcholine(30:0)ChEBI
1-Myristoyl-2-palmitoyl-sn-glycero-3-phosphocholineHMDB
GPCho(14:0/16:0)HMDB
LecithinHMDB
GPCho(30:0)HMDB
PC(14:0/16:0)Lipid Annotator
Chemical FormulaC38H76NO8P
Average Molecular Weight705.9857
Monoisotopic Molecular Weight705.530854925
IUPAC Name(2-{[(2R)-2-(hexadecanoyloxy)-3-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)trimethylazanium
Traditional Namelecithin
CAS Registry Number69525-80-0
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C38H76NO8P/c1-6-8-10-12-14-16-18-19-21-23-25-27-29-31-38(41)47-36(35-46-48(42,43)45-33-32-39(3,4)5)34-44-37(40)30-28-26-24-22-20-17-15-13-11-9-7-2/h36H,6-35H2,1-5H3/t36-/m1/s1
InChI KeyRFVFQQWKPSOBED-PSXMRANNSA-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
logP4.95ALOGPS
logP7.22ChemAxon
logS-7.4ALOGPS
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 Count38ChemAxon
Refractivity206.66 m³·mol⁻¹ChemAxon
Polarizability87.04 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, Positivesplash10-0002-0000915000-bc584558990797312c6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pdi-0090000200-2c15a5a90b5c77a43bb0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0190001000-380e9a694bb22e2c54a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-4190000000-e4fece5b9cba2951ca1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000900-7615039fbfae408d95f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000001900-984ab4028567ba2b66bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0101791100-97808bd3a382a5e63f97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000900-c6fb3bc05eaaa84c86e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zi0-0090012500-75c25faf094705411d6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-2191000000-fe6c58e1684ed4b19b23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000900-b00a0ca4532ff9182094View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000001900-4bbfc80efe35c8e1c7e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0600491100-d3be2cced1b82ac1c455View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000900-ce96887ed69b9e85f7a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-0600000900-fe4e7280392995d009f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-1900412100-713da14b61754e31d304View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000900-4857d5d4f8976860ccc2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0030000900-80adb7a66fc0aee6315eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a96-0090000400-5f272dc8d69ac17f55ecView in MoNA
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 Quantified5.4 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified6.7 +/- 0.7 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified7.1 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified5.68 +/- 0.04 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0007869
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025061
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound129657
PDB IDNot Available
ChEBI ID75062
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(14:0/16:0) + L-Serine → Choline + PS(14:0/16:0)details