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Record Information
Version3.6
Creation Date2010-02-22 11:49:49 UTC
Update Date2016-02-11 01:26:11 UTC
HMDB IDHMDB13334
Secondary Accession NumbersNone
Metabolite Identification
Common Name9,12-Hexadecadienoylcarnitine
Description9,12-Hexadecadienoylcarnitine is an acylcarnitine with C16:2 fatty acid moiety. Acylcarnitine useful in the diagnosis of fatty acid oxidation disorders and differentiation between biochemical phenotypes of medium-chain acyl-CoA dehydrogenase (MCAD) deficiency deficiencyoxidation disorders.(PMID: 12385891 ).
Structure
Thumb
Synonyms
ValueSource
(Z,Z)9,12-HexadecadienoylcarnitineHMDB
9(Z),12(Z)-HexadecadienoylcarnitineHMDB
9,12-HexadecadienylcarnitineHMDB
9Z,12Z-HexadecadienoylcarnitineHMDB
Acyl carnitine C16:2HMDB
Hexadecadienyl-L-carnitineHMDB
Chemical FormulaC23H41NO4
Average Molecular Weight395.5759
Monoisotopic Molecular Weight395.303558805
IUPAC Name(4S)-4-[(9Z,12Z)-hexadeca-9,12-dienoyloxy]-4-(trimethylazaniumyl)butanoate
Traditional Name(4S)-4-[(9Z,12Z)-hexadeca-9,12-dienoyloxy]-4-(trimethylammonio)butanoate
CAS Registry NumberNot Available
SMILES
CCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H]([N+](C)(C)C)CCC([O-])=O
InChI Identifier
InChI=1S/C23H41NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(24(2,3)4)19-20-22(25)26/h7-8,10-11,21H,5-6,9,12-20H2,1-4H3/b8-7-,11-10-/t21-/m0/s1
InChI KeyInChIKey=AHZCIODFJPNPKS-XBDLETADSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Quaternary ammonium salt
  • Carboxylic acid salt
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic zwitterion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.55e-05 mg/mLALOGPS
logP0.54ALOGPS
logP1.64ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)4.17ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 Å2ChemAxon
Rotatable Bond Count18ChemAxon
Refractivity139.24 m3·mol-1ChemAxon
Polarizability48.22 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.01 +/- 0 uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified0.011 +/- 0.002 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified0.0010 (0.0005-0.0040) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB029394
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB13334
Metagene LinkHMDB13334
METLIN IDNot Available
PubChem Compound53481687
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Okun JG, Kolker S, Schulze A, Kohlmuller D, Olgemoller K, Lindner M, Hoffmann GF, Wanders RJ, Mayatepek E: A method for quantitative acylcarnitine profiling in human skin fibroblasts using unlabelled palmitic acid: diagnosis of fatty acid oxidation disorders and differentiation between biochemical phenotypes of MCAD deficiency. Biochim Biophys Acta. 2002 Oct 10;1584(2-3):91-8. [12385891 ]