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Bovine Rumen Metabolome Database



Showing metabocard for PC(16:0/16:0) (RMDB00564)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:58:04
Accession Number RMDB00564
Common Name PC(16:0/16:0)
Description PC(16:0/16:0) 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(16:0/16:0), in particular, consists of two chains of palmitic acid at the C-1 and C-2 positions. The palmitic acid moieties are derived from fish oils, milk fats, vegetable oils and animal fats. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Dipalmitoylphosphatidylcholine (DPPC) is the major constituent of pulmonary surfactant. It is also used for research purposes in studying liposomes, lipid bilayers, and model biological membranes. 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.
Synonyms
  1. GPCho(32:0)
  2. 1,2-dipalmitoyl-rac-glycero-3-phosphocholine
  3. Phosphatidylcholine(16:0/16:0)
  4. Lecithin
  5. Phosphatidylcholine(32:0)
  6. GPCho(16:0/16:0)
  7. DPPC
  8. PC(32:0)
  9. (R)-4-hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-Trioxa-4-phosphapentacosan-1-aminium 4-oxide hydroxide inner salt
  10. (R)-4-hydroxy-N,N,N-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-Trioxa-4-phosphapentacosan-1-aminium 4-oxide inner salt
  11. 1,2-Bis(hexadecanoyl)-sn-glycero-3-phosphocholine
  12. 1,2-Bis(palmitoyl)-sn-glycero-3-phosphocholine
  13. 1,2-Dihexadecanoyl-sn-glycerol-3-phosphorylcholine
  14. 1,2-Dipalmitoyl-3-sn-phosphatidylcholine
  15. 1,2-Dipalmitoyl-L-3-phosphatidylcholine
  16. 1,2-Dipalmitoyl-L-a-lecithin
  17. 1,2-Dipalmitoyl-L-a-phosphatidylcholine
  18. 1,2-Dipalmitoyl-L-lecithin
  19. 1,2-Dipalmitoyl-L-phosphatidylcholine
  20. 1,2-Dipalmitoyl-sn-3-glycerophosphocholine
  21. 1,2-Dipalmitoyl-sn-glycero-3-phosphatidylcholine
  22. 1,2-Dipalmitoyl-sn-glycero-3-phosphocholine
  23. 1,2-Dipalmitoyl-sn-glycero-3-phosphorylcholine
  24. 1,2-Dipalmitoyl-sn-glycerol-3-phosphocholine
  25. 1,2-Dipalmitoyl-sn-glycerophosphocholine
  26. 1,2-Dipalmitoyl-sn-glycerophosphorylcholine
  27. 1,2-Dipalmitoyl-sn-glyceryl-3-phosphocholine
  28. 1,2-Dipalmitoyl-sn-phosphatidylcholine
  29. 1,2-Dipalmitoylglycero-3-phosphocholine
  30. 1,2-L-a-Dipalmitoylphosphatidylcholine
  31. Colfosceril palmitate
  32. Dihexadecanoyl-sn-glycero-3-phosphocholine
  33. Dipalmitoyl L-a-phosphatidylcholine
  34. Dipalmitoyl-L-3-glycerylphosphorylcholine
  35. Dipalmitoyl-L-a-lecithin
  36. Dipalmitoyl-L-a-phosphatidylcholine
  37. Dipalmitoyl-sn-3-phosphatidylcholine
  38. L-1,2-Dipalmitoyl-a-lecithin
  39. L-1,2-Dipalmitoylphosphatidylcholine
  40. L-DPPC
  41. L-Dipalmitoyl lecithin
  42. L-a-1,2-Dipalmitoyl lecithin
  43. L-a-DPPC
  44. L-a-Dipalmitoylecithin
  45. L-a-Dipalmitoyllecithin
  46. L-a-Dipalmitoylphosphatidylcholine
  47. L-b,g-Dipalmitoyl-a-lecithin
  48. L-b,g-Dipalmitoyl-a-phosphatidylcholine
  49. L-b,g-Dipalmitoylphosphatidylcholine
  50. b,g-Dipalmitoyl L-a-phosphatidylcholine
  51. b,g-Dipalmitoyl-L-(a)-lecithin
  52. b,g-Dipalmitoyl-L-phosphatidylcholine
  53. sn-3-Dipalmitoyllecithin
  54. 1,2-Dipalmitoyl-L-alpha-lecithin
  55. 1,2-Dipalmitoyl-L-alpha-phosphatidylcholine
  56. 1,2-L-alpha-Dipalmitoylphosphatidylcholine
  57. Dipalmitoyl L-alpha-phosphatidylcholine
  58. Dipalmitoyl-L-alpha-lecithin
  59. Dipalmitoyl-L-alpha-phosphatidylcholine
  60. L-1,2-Dipalmitoyl-alpha-lecithin
  61. L-alpha-1,2-Dipalmitoyl lecithin
  62. L-alpha-DPPC
  63. L-alpha-Dipalmitoylecithin
  64. L-alpha-Dipalmitoyllecithin
  65. L-alpha-Dipalmitoylphosphatidylcholine
  66. L-b,g-Dipalmitoyl-alpha-lecithin
  67. L-b,g-Dipalmitoyl-alpha-phosphatidylcholine
  68. b,g-Dipalmitoyl L-alpha-phosphatidylcholine
  69. Dipalmitoylphosphatidylcholine
Chemical IUPAC Name 2-[[(2R)-2,3-dihexadecanoyloxypropoxy]-oxido-phosphoryl]oxyethyl-trimethyl-azanium
Chemical Formula C40H80NO8P
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Lipids
Class
  • Phospholipids
Sub Class
  • Phosphatidylcholines
Family
  • Mammalian_Metabolite
Species
  • cation; anion; quaternary ammonium salt; carboxylic acid ester; phosphoric acid ester
Biofunction
  • Membrane component
Application
Source
  • Endogenous
Average Molecular Weight 734.039
Monoisotopic Molecular Weight 733.562134
Isomeric SMILES CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC
Canonical SMILES CCCCCCCCCCCCCCCC(=O)OCC(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC
KEGG Compound ID C00157 Link Image
BioCyc ID PHOSPHATIDYLCHOLINE Link Image
BiGG ID Not Available
Wikipedia Link Dipalmitoylphosphatidylcholine Link Image
METLIN ID 5548 Link Image
PubChem Compound 452110 Link Image
PubChem Substance 10300838 Link Image
ChEBI ID Not Available
CAS Registry Number 63-89-8
InChI Identifier InChI=1/C40H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h38H,6-37H2,1-5H3/t38-/m1/s1
Synthesis Reference Bouirig, H.; Eloy, D.; Jardon, P. Formation and reactivity of the singlet oxygen photosensitized by hypericin in the liposomes of dipalmitoylphosphatidylcholine. Evidence of delayed oxidation. Journal de Chimie Physique et de Physico-Chimie Biologique (1992), 89(6), 1391-411.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 8.15e-11 mg/mL [MEYLAN,WM et al. (1996)]; 2.40e-05 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 5.29 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
Biofluid Location
  • Rumen
Tissue Location Not Available
Concentrations (Normal)
Biofluid Rumen
Value 0.040 +/- 0.03 uM
Age N/A
Sex Female
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
References
  • The rumen metabolome (in preparation)
Concentrations (Abnormal) Not Available
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References
  1. Wikipedia Link Image