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Bovine Rumen Metabolome Database



Showing metabocard for PC(18:2(9Z,12Z)/18:0) (RMDB08135)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2008-09-12 02:31:56
Update Date 2009-05-05 21:03:07
Accession Number RMDB08135
Common Name PC(18:2(9Z,12Z)/18:0)
Description PC(18:2(9Z,12Z)/18:0) 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(18:2(9Z,12Z)/18:0), in particular, consists of one chain of linoleic acid at the C-1 position and one chain of stearic acid at the C-2 position. The linoleic acid moiety is derived from seed oils, while the stearic acid moiety is derived from animal fats, coco butter and sesame 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. GPCho(18:2w6/18:0)
  2. GPCho(36:2)
  3. 1-linoleoyl-2-stearoyl-sn-glycero-3-phosphocholine
  4. Phosphatidylcholine(18:2n6/18:0)
  5. GPCho(18:2/18:0)
  6. PC(18:2/18:0)
  7. PC(36:2)
  8. Lecithin
  9. Phosphatidylcholine(36:2)
  10. PC(18:2w6/18:0)
  11. Phosphatidylcholine(18:2w6/18:0)
  12. PC(18:2n6/18:0)
  13. GPCho(18:2n6/18:0)
  14. Phosphatidylcholine(18:2/18:0)
Chemical IUPAC Name 1-(9Z,12Z-octadecadienoyl)-2-octadecanoyl-sn-glycero-3-phosphocholine
Chemical Formula C44H84NO8P
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 786.113
Monoisotopic Molecular Weight 785.593445
Isomeric SMILES CCCCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCC=C/CC=C/CCCCC)COP([O-])(=O)OCC[N+](C)(C)C
Canonical SMILES CCCCCCCCCCCCCCCCCC(=O)OC(COC(=O)CCCCCCCC=CCC=CCCCCC)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/C44H84NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h14,16,20,22,42H,6-13,15,17-19,21,23-41H2,1-5H3/b16-14-,22-20-/t42-/m1/s1
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 2.22e-05 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 5.80 [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 0.601 +/- 0.735 uM
Age 4-5 years old
Sex Female (lactating)
Condition Normal (0% barley grain in dry matter (DM) basis)
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Concentrations (Abnormal)
Biofluid Rumen
Value 0.02 +/- 0.01 uM
Age 4-5 years old
Sex Female (lactating)
Condition 15% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 0.02 +/- 0.01 uM
Age 4-5 years old
Sex Female (lactating)
Condition 30% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 0.02 +/- 0.006 uM
Age 4-5 years old
Sex Female (lactating)
Condition 45% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References
  1. Wikipedia Link Image