Record Information
Version3.6
Creation Date2008-09-12 01:27:27 UTC
Update Date2013-02-09 00:17:55 UTC
HMDB IDHMDB07868
Secondary Accession NumbersNone
Metabolite Identification
Common NamePC(14:0/15:0)
DescriptionPC(14:0/15:0) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(14:0/15:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of pentadecanoic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the pentadecanoic acid moiety is derived from dairy products and milk fat. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.
Structure
Thumb
Synonyms
  1. 1-Myristoyl-2-pentadecanoyl-sn-glycero-3-phosphocholine
  2. GPCho(14:0/15:0)
  3. GPCho(29:0)
  4. Lecithin
  5. PC(14:0/15:0)
  6. PC(29:0)
  7. Phosphatidylcholine(14:0/15:0)
  8. Phosphatidylcholine(29:0)
Chemical FormulaC37H74NO8P
Average Molecular Weight691.9591
Monoisotopic Molecular Weight691.515204861
IUPAC Nametrimethyl(2-{[(2R)-2-(pentadecanoyloxy)-3-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)azanium
Traditional IUPAC Nametrimethyl(2-{[(2R)-2-(pentadecanoyloxy)-3-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)azanium
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C37H74NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-37(40)46-35(34-45-47(41,42)44-32-31-38(3,4)5)33-43-36(39)29-27-25-23-21-19-17-15-13-11-9-7-2/h35H,6-34H2,1-5H3/t35-/m1/s1
InChI KeyJERIBPHBOOFETI-PGUFJCEWSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Diacylglycerophosphocholines(Lipidmaps)
Substituents
  • Carboxylic Acid Ester
  • Choline
  • Dicarboxylic Acid Derivative
  • Fatty Acid Ester
  • Glycero 3 Phosphocholine
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphocholine
  • Phosphoethanolamine
  • Phosphoric Acid Ester
  • Quaternary Ammonium Salt
Direct ParentPhosphatidylcholines
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Energy source
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • 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
water solubility3.370E-05 g/LALOGPS
logP4.76ALOGPS
logP6.78ChemAxon
logS-7.3ALOGPS
pKa (strongest acidic)1.86ChemAxon
pKa (strongest basic)-6.7ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count0ChemAxon
polar surface area111.19ChemAxon
rotatable bond count37ChemAxon
refractivity202.06ChemAxon
polarizability84.86ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Location
  • All Tissues
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations Help
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0.027939066 +/- 0.002849979 uMAdult (>18 years old)BothNormal (Most Probable)Calculated using MetaboAnalyst
Blood10.56666667 +/- 0.642910051 uMAdult (>18 years old)BothNormal (Upper Limit)Calculated using MetaboAnalyst
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB025060
KNApSAcK IDNot Available
Chemspider ID24766546
KEGG Compound IDC00157
BioCyc ID PHOSPHATIDYLCHOLINE
BiGG IDNot Available
Wikipedia LinkLecithin
NuGOwiki LinkHMDB07868
Metagene LinkHMDB07868
METLIN IDNot Available
PubChem Compound24778611
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 50 proteins. There are 78 proteins in total.

Enzymes

Gene Name:
LYPLA1
Uniprot ID:
O75608
Gene Name:
PLA2G15
Uniprot ID:
Q8NCC3
Gene Name:
PLA2G5
Uniprot ID:
P39877
Gene Name:
PLA2G2F
Uniprot ID:
Q9BZM2
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Gene Name:
PLA2G10
Uniprot ID:
O15496
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Gene Name:
LYPLA2
Uniprot ID:
O95372
Gene Name:
PLA2G12A
Uniprot ID:
Q9BZM1
Gene Name:
CLC
Uniprot ID:
Q05315
Gene Name:
PLA2G2A
Uniprot ID:
P14555
Gene Name:
PLA2G2D
Uniprot ID:
Q9UNK4
Gene Name:
PLD2
Uniprot ID:
O14939
Gene Name:
PLD1
Uniprot ID:
Q13393
Gene Name:
PLA2G4C
Uniprot ID:
Q9UP65
Gene Name:
PLA2G3
Uniprot ID:
Q9NZ20
Gene Name:
CHKA
Uniprot ID:
P35790
Gene Name:
LRAT
Uniprot ID:
O95237
Gene Name:
PLSCR1
Uniprot ID:
O15162
Gene Name:
PTDSS1
Uniprot ID:
P48651
Gene Name:
PLTP
Uniprot ID:
P55058
Gene Name:
CHPT1
Uniprot ID:
Q8WUD6
Gene Name:
MOGAT2
Uniprot ID:
Q3SYC2
Gene Name:
LPCAT3
Uniprot ID:
Q6P1A2

Transporters

Gene Name:
ABCB4
Uniprot ID:
P21439

Only showing the first 50 proteins. There are 78 proteins in total.