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Bovine Rumen Metabolome Database



Showing metabocard for Linoleyl carnitine (RMDB06469)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2007-05-23 11:45:07
Update Date 2011-06-03 10:40:57
Accession Number RMDB06469
Common Name Linoleyl carnitine
Description Linoleyl carnitine is a long-chain acyl fatty acid derivative ester of carnitine. Long-chain acyl fatty acid derivatives accumulate in the cytosol and serum of patients suffering of mitochondrial carnitine palmitoyltransferase II (CPT II, EC 2.3.1.12) deficiency, the most common inherited disorder of lipid metabolism in adults. carnitine palmitoyltransferase II deficiency is an autosomal recessive disorder of fatty acid metabolism presenting as two clinical phenotypes: (i) a severe infantile hepatocardiomuscular form and (ii) a milder adult muscular form. Energy production from long-chain fatty acids (LCFAs) requires the transport of LCFAs into the mitochondrial matrix. This transport is carnitine-dependent and involves translocation machinery. mitochondrial fatty acid oxidation disorders cause hypoglycaemia, hepatic dysfunction, myopathy, cardiomyopathy and encephalopathy. Patients with end-stage renal disease (ESRD) undergoing long-term haemodialysis exhibit elevated acylcarnitine concentrations. (PMID: 11999976, 10682306, 15025677, 16168195)
Synonyms
  1. Linoleic acid carnitine
  2. Linoleoyl carnitine
  3. 3-carboxy-N,N,N-trimethyl-2-[[(9Z,12Z)-1-oxo-9,12-octadecadienyl]oxy]-1-Propanaminium
  4. 3-carboxy-N,N,N-trimethyl-2-[(1-oxo-9,12-octadecadienyl)oxy]-1-Propanaminium
  5. alpha-Linoleoylcarnitine
  6. Decadienylcarnitine
  7. 9,12-octadecadienylcarnitine
  8. 9,12-octadecadienoylcarnitine
Chemical IUPAC Name Not Available
Chemical Formula C25H45NO4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Quaternary Amines
Sub Class
  • Long chain acyl carnitines
Family
  • Mammalian_Metabolite
Species
  • cation; anion; quaternary ammonium salt; carboxylic acid salt; carboxylic acid ester; alkene
Biofunction
  • Lipid catabolism, Fatty acid transport, Energy production
Application
Source
  • Endogenous
Average Molecular Weight 423.629
Monoisotopic Molecular Weight 423.334869
Isomeric SMILES CCCCCC=C/CC=C/CCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C
Canonical SMILES CCCCCC=CCC=CCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID 2614398 Link Image
Wikipedia Link Not Available
METLIN ID Not Available
PubChem Compound Not Available
PubChem Substance Not Available
ChEBI ID Not Available
CAS Registry Number 36816-10-1
InChI Identifier InChI=1/C25H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(21-24(27)28)22-26(2,3)4/h9-10,12-13,23H,5-8,11,14-22H2,1-4H3/b10-9-,13-12-/t23-/m1/s1
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 8.62e-06 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 1.46 [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 Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
  • mitochondria
Biofluid Location
  • Rumen
Tissue Location Not Available
Concentrations (Normal)
Biofluid Rumen
Value 0.007 +/- 0.001 uM
Age N/A
Sex N/A
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 Not Available