Showing metabocard for PC(14:0/14:0) (BMDB0007866)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:46:00 UTC
Update Date2020-05-21 16:28:16 UTC
BMDB IDBMDB0007866
Secondary Accession Numbers
  • BMDB07866
Metabolite Identification
Common NamePC(14:0/14:0)
DescriptionPC(16:1(9Z)/20:0), also known as dimyristoyl lecithin or GPC(28:0), 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(16:1(9Z)/20:0) is considered to be a glycerophosphocholine lipid molecule. PC(16:1(9Z)/20:0) is a drug. PC(16:1(9Z)/20:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(16:1(9Z)/20:0) exists in all eukaryotes, ranging from yeast to humans. PC(16:1(9Z)/20:0) participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and PC(16:1(9Z)/20:0) can be biosynthesized from S-adenosylmethionine and pe-nme2(16:1(9Z)/20:0) through its interaction with the enzyme phosphatidylethanolamine N-methyltransferase. Furthermore, Cytidine monophosphate and PC(16:1(9Z)/20:0) can be biosynthesized from CDP-choline and DG(16:1(9Z)/20:0/0:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. Finally, PC(16:1(9Z)/20:0) and L-serine can be converted into choline and PS(16:1(9Z)/20:0) through the action of the enzyme phosphatidylserine synthase. In cattle, PC(16:1(9Z)/20:0) is involved in a couple of metabolic pathways, which include phosphatidylcholine biosynthesis PC(16:1(9Z)/20:0) pathway and phosphatidylethanolamine biosynthesis pe(16:1(9Z)/20:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-Di-O-tetradecanoyl-sn-glycero-3-phosphocholineChEBI
1,2-Dimyristoyl-GPCChEBI
1,2-Dimyristoyl-L-3-phosphatidylcholineChEBI
1,2-Dimyristoyl-sn-glycero-3-phosphocholineChEBI
1,2-DimyristoylphosphatidylcholineChEBI
1,2-Ditetradecanoyl-sn-glycero-3-phosphocholineChEBI
Dimyristoyl lecithinChEBI
Dimyristoyl phosphatidylcholineChEBI
DimyristoylphosphatidylcholineChEBI
DMPCChEBI
GPC(14:0/14:0)ChEBI
GPC(28:0)ChEBI
PC(28:0)ChEBI
Phosphatidylcholine(14:0/14:0)ChEBI
Phosphatidylcholine(28:0)ChEBI
1,2 Ditetradecanoyl glycero 3 phosphocholineHMDB
1,2-Ditetradecanoyl-glycero-3-phosphocholineHMDB
1,2-Ditetradecyl-glycero-3-phosphocholineHMDB
DMCPHMDB
DimyristoyllecithinHMDB
1,2 Dimyristoyl glycero 3 phosphorylcholineHMDB
1,2 Ditetradecyl glycero 3 phosphocholineHMDB
1,2-Dimyristoyl-glycero-3-phosphorylcholineHMDB
LecithinHMDB
1,2-Dimyristoyl-rac-glycero-3-phosphocholineHMDB
GPCho(28:0)HMDB
GPCho(14:0/14:0)HMDB
1,2-Ditetradecanoyl-rac-glycero-3-phosphocholineHMDB
PC(14:0/14:0)Lipid Annotator, ChEBI
Chemical FormulaC36H72NO8P
Average Molecular Weight677.9325
Monoisotopic Molecular Weight677.499554797
IUPAC Name(2-{[(2R)-2,3-bis(tetradecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-2,3-bis(tetradecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry Number18194-24-6
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC
InChI Identifier
InChI=1S/C36H72NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-35(38)42-32-34(33-44-46(40,41)43-31-30-37(3,4)5)45-36(39)29-27-25-23-21-19-17-15-13-11-9-7-2/h34H,6-33H2,1-5H3/t34-/m1/s1
InChI KeyCITHEXJVPOWHKC-UUWRZZSWSA-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
StatusExpected but not 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
logP4.57ALOGPS
logP6.34ChemAxon
logS-7.3ALOGPS
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 Count36ChemAxon
Refractivity197.46 m³·mol⁻¹ChemAxon
Polarizability82.6 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0007866
DrugBank IDDB09530
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5459377
PDB IDMC3
ChEBI ID45240
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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(14:0/14:0) + L-Serine → Choline + PS(14:0/14:0)details