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Bovine Metabolome Database



Showing metabocard for L-Hexanoylcarnitine (BMDB00756)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:58:15
Accession Number BMDB00756
Common Name L-Hexanoylcarnitine
Description L-Hexanoylcarnitine is an acylcarnitine. Numerous disorders have been described that lead to disturbances in energy production and in intermediary metabolism in the organism which are characterized by the production and excretion of unusual acylcarnitines. A mutation in the gene coding for carnitine-acylcarnitine translocase or the OCTN2 transporter aetiologically causes a carnitine deficiency that results in poor intestinal absorption of dietary L-carnitine, its impaired reabsorption by the kidney and, consequently, in increased urinary loss of L-carnitine. Determination of the qualitative pattern of acylcarnitines can be of diagnostic and therapeutic importance. The betaine structure of carnitine requires special analytical procedures for recording. The ionic nature of L-carnitine causes a high water solubility which decreases with increasing chain length of the ester group in the acylcarnitines. Therefore, the distribution of L-carnitine and acylcarnitines in various organs is defined by their function and their physico-chemical properties as well. High performance liquid chromatography (HPLC) permits screening for free and total carnitine, as well as complete quantitative acylcarnitine determination, including the long-chain acylcarnitine profile. (PMID: 17508264, Monatshefte fuer Chemie (2005), 136(8), 1279-1291., Int J Mass Spectrom. 1999;188:39-52.) Hexanoylcarnitine is a medium-chain acylcarnitine present in the urine of patients with medium-chain acyl-CoA dehydrogenase deficiency (PubMed ID 1635814 )
Synonyms
  1. (R)-3-carboxy-N,N,N-trimethyl-2-[(1-oxohexyl)oxy]-1-Propanaminium inner salt
  2. (R)-Caproylcarnitine
  3. Hexanoic acid ester with L-(3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner salt
  4. Hexanoyl-L-carnitine
  5. L-Carnitine hexanoyl ester
  6. L-Hexanoic acid ester with (3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner salt
  7. L-Hexanoylcarnitine
  8. Hexanoate
  9. L-Hexanoate
  10. Hexanoic acid
  11. L-Hexanoic acid
Chemical IUPAC Name Not Available
Chemical Formula C13H25NO4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Quaternary Amines
Sub Class
  • Short chain acyl carnitines
Family
  • Mammalian_Metabolite
Species
  • cation; anion; quaternary ammonium salt; carboxylic acid salt; carboxylic acid ester
Biofunction
  • Lipid catabolism, Fatty acid transport, Energy production
Application
Source
  • Endogenous
Average Molecular Weight 259.342
Monoisotopic Molecular Weight 259.178345
Isomeric SMILES CCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C
Canonical SMILES CCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
METLIN ID 3548 Link Image
PubChem Compound Not Available
PubChem Substance Not Available
ChEBI ID Not Available
CAS Registry Number 22671-29-0
InChI Identifier InChI=1/C13H25NO4/c1-5-6-7-8-13(17)18-11(9-12(15)16)10-14(2,3)4/h11H,5-10H2,1-4H3/t11-/m1/s1
Synthesis Reference Nakanishi, Toyofumi; Shimizu, Akira; Arimoto, Masao; Kanai, Michiko. Synthesis of acylcarnitines for differential diagnosis of metabolic disorders. Nippon Iyo Masu Supekutoru Gakkai Koenshu (1993), 18 129-32.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 4.30e-03 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -1.68 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
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2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
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Predicted 1H NMR Spectrum Show Image
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Mass Spectrum
Low Energy
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References Not Available