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Human Metabolome Database Version 3.5

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Showing metabocard for Heptadecanoyl carnitine (HMDB06210)

Record Information
Version 3.5
Creation Date 2007-05-22 11:34:16 -0600
Update Date 2013-05-29 13:42:59 -0600
HMDB ID HMDB06210
Secondary Accession Numbers None
Metabolite Identification
Common Name Heptadecanoyl carnitine
Description Heptadecanoyl carnitine 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 Link_out, Monatshefte fuer Chemie (2005), 136(8), 1279-1291., Int J Mass Spectrom. 1999;188:39-52.).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3-Carboxy-N,N,N-trimethyl-2-[(1-oxoheptadecyl)oxy]-1-Propanaminium inner salt
  2. Carnitine heptadecanoate
  3. Carnitine heptadecanoic acid
  4. Heptadecanoate
  5. Heptadecanoate carnitine
  6. Heptadecanoic acid
  7. Heptadecanoyl acid carnitine
  8. Heptadecanoyl carnitine
  9. Heptadecanoylcarnitine
Chemical Formula C24H47NO4
Average Molecular Weight 413.6343
Monoisotopic Molecular Weight 413.350508997
IUPAC Name 3-(heptadecanoyloxy)-4-(trimethylazaniumyl)butanoate
Traditional IUPAC Name 3-(heptadecanoyloxy)-4-(trimethylaminio)butanoate
CAS Registry Number 106182-29-0
SMILES CCCCCCCCCCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C
InChI Identifier InChI=1S/C24H47NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-24(28)29-22(20-23(26)27)21-25(2,3)4/h22H,5-21H2,1-4H3
InChI Key DWSFAVOTORHAAL-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class Acyl Carnitines
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
Substituents
  • Carboxylic Acid Ester
  • Carboxylic Acid Salt
  • Carnitine
  • Choline
  • Dicarboxylic Acid Derivative
  • Quaternary Ammonium Salt
Direct Parent Acyl Carnitines
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Lipid catabolism, Fatty acid transport, Energy production
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1.050E-05 g/L ALOGPS
LogP 2.17 ALOGPS
LogP 2.48 ChemAxon
LogS -7.65 ALOGPS
pKa (strongest acidic) 4.22 ChemAxon
pKa (strongest basic) -7.1 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 66.43 A2 ChemAxon
Rotatable Bond Count 21 ChemAxon
Refractivity 141.68 ChemAxon
Polarizability 52.16 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023836
KNApSAcK ID Not Available
Chemspider ID 21233951 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID 2422209 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB06210 Link_out
Metagene Link HMDB06210 Link_out
METLIN ID Not Available
PubChem Compound 53477803 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Huysmans, L.; Nizigiyimana, L.; Van den Heuvel, H.; Claeys, M. Charge-remote molecular hydrogen removal in protonated and alkali-cationized long-chain fatty acid esters upon cesium ion bombardment. International Journal of Mass Spectrometry (1999), 188(1/2), 39-52.
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Pierre G, Macdonald A, Gray G, Hendriksz C, Preece MA, Chakrapani A: Prospective treatment in carnitine-acylcarnitine translocase deficiency. J Inherit Metab Dis. 2007 Oct;30(5):815. Epub 2007 May 12. Pubmed: 17508264 Link_out