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Showing metabocard for Hexadecanedioic acid mono-L-carnitine ester (HMDB00712)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:09 -0700
HMDB ID HMDB00712
Secondary Accession Numbers None
Metabolite Identification
Common Name Hexadecanedioic acid mono-L-carnitine ester
Description Hexadecanedioic acid mono-L-carnitine ester is an intermediate in the formation of hexadecanedioylcarnitine. Hexadecanedioic acid has been shown to be activated by ATP-Mg2+ and CoA and transported into the inner mitochondrial compartment as the mono-L-carnitine ester. (PMID: 4703570 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (R)-3-carboxy-2-[(15-carboxy-1-oxopentadecyl)oxy]-N,N,N-trimethyl-1-Propanaminium inner salt
  2. Hexadecanedioate
  3. Hexadecanedioic acid
  4. Hexadecanedioic acid mono-L-carnitine ester
Chemical Formula C23H43NO6
Average Molecular Weight 429.5906
Monoisotopic Molecular Weight 429.309038113
IUPAC Name 3-[(15-carboxypentadecanoyl)oxy]-4-(trimethylazaniumyl)butanoate
Traditional IUPAC Name 3-[(15-carboxypentadecanoyl)oxy]-4-(trimethylaminio)butanoate
CAS Registry Number 42150-38-9
SMILES C[N+](C)(C)CC(CC([O-])=O)OC(=O)CCCCCCCCCCCCCCC(O)=O
InChI Identifier InChI=1S/C23H43NO6/c1-24(2,3)19-20(18-22(27)28)30-23(29)17-15-13-11-9-7-5-4-6-8-10-12-14-16-21(25)26/h20H,4-19H2,1-3H3,(H-,25,26,27,28)
InChI Key UNHCPLSWMNPZTD-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class Acyl Carnitines
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Amino Fatty Acids
  • Organic Compounds
Substituents
  • Carboxylic Acid
  • Carboxylic Acid Ester
  • Carboxylic Acid Salt
  • Carnitine
  • Choline
  • Quaternary Ammonium Salt
  • Tricarboxylic Acid Derivative
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
  • 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 1.100E-04 g/L ALOGPS
LogP 1.00 ALOGPS
LogP 0.71 ChemAxon
LogS -6.64 ALOGPS
pKa (strongest acidic) 4.14 ChemAxon
pKa (strongest basic) -7.1 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 103.73 A2 ChemAxon
Rotatable Bond Count 21 ChemAxon
Refractivity 138.74 ChemAxon
Polarizability 51.48 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid Locations Not Available
Tissue Location
  • Liver
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
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022198
KNApSAcK ID Not Available
Chemspider ID 17215993 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00712 Link_out
Metagene Link HMDB00712 Link_out
METLIN ID 5680 Link_out
PubChem Compound 566787 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Pettersen JE: In vitro studies on the metabolism of hexadecanedioic acid and its mono-L-carnitine ester. Biochim Biophys Acta. 1973 Apr 13;306(1):1-14. Pubmed: 4703570 Link_out
  2. Pettersen JE, Aas M. Subcellular localization of hexadecanedioic acid activation in human liver. J Lipid Res. 1974 Nov;15(6):551-6.