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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2010-02-22 11:49:49 UTC
Update Date2020-09-17 06:33:50 UTC
HMDB IDHMDB0013334
Secondary Accession Numbers
  • HMDB13334
Metabolite Identification
Common Name9,12-Hexadecadienoylcarnitine
Description9,12-Hexadecadienoylcarnitine is an acylcarnitine with C16:2 fatty acid moiety. Acylcarnitine is useful in the diagnosis of fatty acid oxidation disorders and differentiation between biochemical phenotypes of medium-chain acyl-CoA dehydrogenase (MCAD) deficiency deficient oxidation disorders (PMID: 12385891 ).
Structure
Data?1600324430
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
(3R)-3-[(9Z,12Z)-Hexadeca-9,12-dienoyloxy]-4-(trimethylazaniumyl)butanoic acidGenerator
Acylcarnitine C16:2HMDB
Acylcarnitine C16:2(9Z,12Z)HMDB
C16:2 CarnitineHMDB
C16:2(9Z,12Z) CarnitineHMDB
Chemical FormulaC23H42NO4
Average Molecular Weight396.591
Monoisotopic Molecular Weight396.310835257
IUPAC Name[(2R)-3-carboxy-2-[(9Z,12Z)-hexadeca-9,12-dienoyloxy]propyl]trimethylazanium
Traditional Name[(2R)-3-carboxy-2-[(9Z,12Z)-hexadeca-9,12-dienoyloxy]propyl]trimethylazanium
CAS Registry Number1911579-97-9
SMILES
CCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C23H41NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4/h7-8,10-11,21H,5-6,9,12-20H2,1-4H3/p+1/b8-7-,11-10-/t21-/m1/s1
InChI KeyCMVGCHSJDXKPBB-ROVXQSMVSA-O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentAcyl carnitines
Alternative Parents
Substituents
  • Acyl-carnitine
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility1.6e-05 g/LALOGPS
logP1.58ALOGPS
logP1.31ChemAxon
logS-7ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity128.47 m³·mol⁻¹ChemAxon
Polarizability47.9 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.01 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0080-0.0250 uMAdult (>18 years old)BothNormal details
FecesDetected and Quantified0.19 +/- 0.09 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0.11 +/- 0.04 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified0.011 +/- 0.002 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified0.0-0.01 umol/mmol creatinineNewborn (0-30 days old)BothNormal
    • López Hernández Y...
details
UrineDetected and Quantified0.0010 (0.0005-0.0040) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.011 (0.0057) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH 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. [PubMed:12385891 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.