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Bovine Rumen Metabolome Database



Showing metabocard for PC(18:1(9Z)/20:0) (RMDB08109)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2008-09-12 02:31:30
Update Date 2009-05-05 21:03:03
Accession Number RMDB08109
Common Name PC(18:1(9Z)/20:0)
Description PC(18:1(9Z)/20:0) 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(18:1(9Z)/20:0), in particular, consists of one chain of oleic acid at the C-1 position and one chain of arachidic acid at the C-2 position. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the arachidic acid moiety is derived from peanut oil. 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.
Synonyms
  1. Phosphatidylcholine(18:1/20:0)
  2. Phosphatidylcholine(38:1)
  3. Phosphatidylcholine(18:1w9/20:0)
  4. PC(18:1/20:0)
  5. GPCho(18:1w9/20:0)
  6. PC(18:1w9/20:0)
  7. Lecithin
  8. PC(18:1n9/20:0)
  9. PC(38:1)
  10. Phosphatidylcholine(18:1n9/20:0)
  11. GPCho(18:1n9/20:0)
  12. GPCho(18:1/20:0)
  13. 1-oleoyl-2-arachidonyl-sn-glycero-3-phosphocholine
  14. GPCho(38:1)
Chemical IUPAC Name 1-(9Z-octadecenoyl)-2-eicosanoyl-sn-glycero-3-phosphocholine
Chemical Formula C46H90NO8P
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; alkene
Biofunction
  • Membrane component; Energy source; Cell signaling
Application
Source
  • Endogenous
Average Molecular Weight 816.182
Monoisotopic Molecular Weight 815.640381
Isomeric SMILES CCCCCCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCC=C/CCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
Canonical SMILES CCCCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)CCCCCCCC=CCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C
KEGG Compound ID C00157 Link Image
BioCyc ID PHOSPHATIDYLCHOLINE Link Image
BiGG ID Not Available
Wikipedia Link Lecithin Link Image
METLIN ID Not Available
PubChem Compound Not Available
PubChem Substance Not Available
ChEBI ID Not Available
CAS Registry Number Not Available
InChI Identifier InChI=1/C46H90NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h21,24,44H,6-20,22-23,25-43H2,1-5H3/b24-21-/t44-/m1/s1
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 1.89e-05 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 6.20 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
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 Not Available
Not Available
Predicted 13C NMR Spectrum Not Available
Not Available
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane
Biofluid Location
  • Rumen
Tissue Location
Concentrations (Normal)
Biofluid Rumen
Value 0.031 +/- 0.003 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