cis-5-Tetradecenoylcarnitine (CHEM022739)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:50:15 UTC
Update Date2016-11-09 01:17:34 UTC
Accession NumberCHEM022739
Identification
Common Namecis-5-Tetradecenoylcarnitine
ClassSmall Molecule
DescriptionAn O-acylcarnitine having (5Z)-tetradecenoyl as the acyl substituent.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-[(5Z)-Tetradec-5-enoyloxy]-4-(trimethylammonio)butanoateChEBI
3-[(5Z)-Tetradec-5-enoyloxy]-4-(trimethylammonio)butanoic acidGenerator
cis-5-TetradecenoylcarnitineChEBI
Chemical FormulaC21H39NO4
Average Molecular Mass369.539 g/mol
Monoisotopic Mass369.288 g/mol
CAS Registry Number835598-21-5
IUPAC Name3-[(5Z)-tetradec-5-enoyloxy]-4-(trimethylazaniumyl)butanoate
Traditional Namecis-5-tetradecenoylcarnitine
SMILESCCCCCCCC\C=C/CCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C
InChI IdentifierInChI=1S/C21H39NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-21(25)26-19(17-20(23)24)18-22(2,3)4/h12-13,19H,5-11,14-18H2,1-4H3/b13-12-
InChI KeyNNCBVXBBLABOCB-SEYXRHQNSA-N
Chemical Taxonomy
Description 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 salt
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.7e-05 g/LALOGPS
logP0.48ALOGPS
logP0.78ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)4.24ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity128.99 m³·mol⁻¹ChemAxon
Polarizability44.6 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9210000000-d55933555203a81af3b0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fkc-0729000000-b7724178fd672abeda7cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-1900000000-a2f60fad8c99a570c7b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02fx-4900000000-6ae1e898595b8e8b61f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-a5108e2a8a5c949c7942Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-1289000000-351e00d1ad0b6a3015e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-7590000000-8eeb0dac52aa2c1d6246Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-1a5965dc435463ee085fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-9005000000-84dcf946c3b41ee8ec83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-e9262cbaff8cb4ad0ba6Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002014
FooDB IDFDB022796
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6437
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID17216151
ChEBI ID73060
PubChem Compound ID22833575
Kegg Compound IDNot Available
YMDB IDYMDB01532
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23315938
2. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)
3. Strauss AW, Powell CK, Hale DE, Anderson MM, Ahuja A, Brackett JC, Sims HF: Molecular basis of human mitochondrial very-long-chain acyl-CoA dehydrogenase deficiency causing cardiomyopathy and sudden death in childhood. Proc Natl Acad Sci U S A. 1995 Nov 7;92(23):10496-500.
4. Shigematsu Y, Hirano S, Hata I, Tanaka Y, Sudo M, Tajima T, Sakura N, Yamaguchi S, Takayanagi M: Selective screening for fatty acid oxidation disorders by tandem mass spectrometry: difficulties in practical discrimination. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):63-72.
5. Wood JC, Magera MJ, Rinaldo P, Seashore MR, Strauss AW, Friedman A: Diagnosis of very long chain acyl-dehydrogenase deficiency from an infant's newborn screening card. Pediatrics. 2001 Jul;108(1):E19.
6. Archie JP Jr: Splenic artery stump back pressure. Am Surg. 1992 Aug;58(8):504-5.
7. FRITZ IB: Action of carnitine on long chain fatty acid oxidation by liver. Am J Physiol. 1959 Aug;197:297-304. doi: 10.1152/ajplegacy.1959.197.2.297.
8. Reuter SE, Evans AM: Carnitine and acylcarnitines: pharmacokinetic, pharmacological and clinical aspects. Clin Pharmacokinet. 2012 Sep 1;51(9):553-72. doi: 10.1007/BF03261931.
9. Hisahara S, Matsushita T, Furuyama H, Tajima G, Shigematsu Y, Imai T, Shimohama S: A heterozygous missense mutation in adolescent-onset very long-chain acyl-CoA dehydrogenase deficiency with exercise-induced rhabdomyolysis. Tohoku J Exp Med. 2015 Apr;235(4):305-10. doi: 10.1620/tjem.235.305.
10. Laforet P, Acquaviva-Bourdain C, Rigal O, Brivet M, Penisson-Besnier I, Chabrol B, Chaigne D, Boespflug-Tanguy O, Laroche C, Bedat-Millet AL, Behin A, Delevaux I, Lombes A, Andresen BS, Eymard B, Vianey-Saban C: Diagnostic assessment and long-term follow-up of 13 patients with Very Long-Chain Acyl-Coenzyme A dehydrogenase (VLCAD) deficiency. Neuromuscul Disord. 2009 May;19(5):324-9. doi: 10.1016/j.nmd.2009.02.007. Epub 2009 Mar 26.
11. Tajima G, Sakura N, Shirao K, Okada S, Tsumura M, Nishimura Y, Ono H, Hasegawa Y, Hata I, Naito E, Yamaguchi S, Shigematsu Y, Kobayashi M: Development of a new enzymatic diagnosis method for very-long-chain Acyl-CoA dehydrogenase deficiency by detecting 2-hexadecenoyl-CoA production and its application in tandem mass spectrometry-based selective screening and newborn screening in Japan. Pediatr Res. 2008 Dec;64(6):667-72. doi: 10.1203/PDR.0b013e318187cc44.
12. Das AM, Illsinger S, Lucke T, Hartmann H, Ruiter JP, Steuerwald U, Waterham HR, Duran M, Wanders RJ: Isolated mitochondrial long-chain ketoacyl-CoA thiolase deficiency resulting from mutations in the HADHB gene. Clin Chem. 2006 Mar;52(3):530-4. doi: 10.1373/clinchem.2005.062000. Epub 2006 Jan 19.
13. Abu Bakar MH, Sarmidi MR: Association of cultured myotubes and fasting plasma metabolite profiles with mitochondrial dysfunction in type 2 diabetes subjects. Mol Biosyst. 2017 Aug 22;13(9):1838-1853. doi: 10.1039/c7mb00333a.
14. Lepori V, Muhlhause F, Sewell AC, Jagannathan V, Janzen N, Rosati M, Alves de Sousa FMM, Tschopp A, Schupbach G, Matiasek K, Tipold A, Leeb T, Kornberg M: A Nonsense Variant in the ACADVL Gene in German Hunting Terriers with Exercise Induced Metabolic Myopathy. G3 (Bethesda). 2018 May 4;8(5):1545-1554. doi: 10.1534/g3.118.200084.
15. Chen Y, Li C, Liu L, Guo F, Li S, Huang L, Sun C, Feng R: Serum metabonomics of NAFLD plus T2DM based on liquid chromatography-mass spectrometry. Clin Biochem. 2016 Sep;49(13-14):962-6. doi: 10.1016/j.clinbiochem.2016.05.016. Epub 2016 May 20.
16. Mai M, Tonjes A, Kovacs P, Stumvoll M, Fiedler GM, Leichtle AB: Serum levels of acylcarnitines are altered in prediabetic conditions. PLoS One. 2013 Dec 16;8(12):e82459. doi: 10.1371/journal.pone.0082459. eCollection 2013.
17. Bruce CR, Hoy AJ, Turner N, Watt MJ, Allen TL, Carpenter K, Cooney GJ, Febbraio MA, Kraegen EW: Overexpression of carnitine palmitoyltransferase-1 in skeletal muscle is sufficient to enhance fatty acid oxidation and improve high-fat diet-induced insulin resistance. Diabetes. 2009 Mar;58(3):550-8. doi: 10.2337/db08-1078. Epub 2008 Dec 10.
18. Schooneman MG, Vaz FM, Houten SM, Soeters MR: Acylcarnitines: reflecting or inflicting insulin resistance? Diabetes. 2013 Jan;62(1):1-8. doi: 10.2337/db12-0466.
19. Ahmad T, Kelly JP, McGarrah RW, Hellkamp AS, Fiuzat M, Testani JM, Wang TS, Verma A, Samsky MD, Donahue MP, Ilkayeva OR, Bowles DE, Patel CB, Milano CA, Rogers JG, Felker GM, O'Connor CM, Shah SH, Kraus WE: Prognostic Implications of Long-Chain Acylcarnitines in Heart Failure and Reversibility With Mechanical Circulatory Support. J Am Coll Cardiol. 2016 Jan 26;67(3):291-9. doi: 10.1016/j.jacc.2015.10.079.