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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-02-24 01:48:23 UTC
Update Date2022-10-24 19:44:18 UTC
HMDB IDHMDB0240780
Secondary Accession NumbersNone
Metabolite Identification
Common NameO-Linoleoylcarnitine
DescriptionO-Linoleoylcarnitine is an acylcarnitine. More specifically, it is an linoleic ester of carnitine. Acylcarnitines were first discovered more than 70 year ago (PMID: 13825279 ). It is believed that there are more than 1000 types of acylcarnitines in the human body. The general role of acylcarnitines is to transport acyl-groups (organic acids and fatty acids) from the cytoplasm into the mitochondria so that they can be broken down to produce energy. This process is known as beta-oxidation. According to a recent review (PMID: 35710135 ), acylcarnitines (ACs) can be classified into 9 different categories depending on the type and size of their acyl-group: 1) short-chain ACs; 2) medium-chain ACs; 3) long-chain ACs; 4) very long-chain ACs; 5) hydroxy ACs; 6) branched chain ACs; 7) unsaturated ACs; 8) dicarboxylic ACs and 9) miscellaneous ACs. Short-chain ACs have acyl-groups with two to five carbons (C2-C5), medium-chain ACs have acyl-groups with six to thirteen carbons (C6-C13), long-chain ACs have acyl-groups with fourteen to twenty once carbons (C14-C21) and very long-chain ACs have acyl groups with more than 22 carbons. O-Linoleoylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine O-Linoleoylcarnitine is generally formed through esterification with long-chain fatty acids obtained from the diet. The main function of most long-chain acylcarnitines is to ensure long chain fatty acid transport into the mitochondria (PMID: 22804748 ). Altered levels of long-chain acylcarnitines can serve as useful markers for inherited disorders of long-chain fatty acid metabolism. In particular O-Linoleoylcarnitine is elevated in the blood or plasma of individuals with Parkinson disease (PMID: 29294246 ), chronic heart failure (PMID: 26796394 , PMID: 27473038 ), carnitine/acylcarnitine translocase (CACT) deficiency (PMID: 15057979 ), and ischaemia/reperfusion (PMID: 26936967 , PMID: 22607863 , PMID: 24468136 ). Carnitine palmitoyltransferase I (CPT I, EC:2.3.1.21) is involved in the synthesis of long-chain acylcarnitines (more than C12) on the mitochondrial outer membrane. Elevated serum/plasma levels of long-chain acylcarnitines are not only markers for incomplete FA oxidation but also are indicators of altered carbohydrate and lipid metabolism. High serum concentrations of long-chain acylcarnitines in the postprandial or fed state are markers of insulin resistance and arise from insulin's inability to inhibit CPT-1-dependent fatty acid metabolism in muscles and the heart (PMID: 19073774 ). Increased intracellular content of long-chain acylcarnitines is thought to serve as a feedback inhibition mechanism of insulin action (PMID: 23258903 ). In healthy subjects, increased concentrations of insulin effectively inhibits long-chain acylcarnitine production. Several studies have also found increased levels of circulating long-chain acylcarnitines in chronic heart failure patients (PMID: 26796394 ). The study of acylcarnitines is an active area of research and it is likely that many novel acylcarnitines will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered. An excellent review of the current state of knowledge for acylcarnitines is available (PMID: 35710135 ).
Structure
Thumb
Synonyms
ValueSource
(9Z,12Z)-Octadeca-9,12-dienoylcarnitineChEBI
3-[(9Z,12Z)-Octadeca-9,12-dienoyloxy]-4-(trimethylammonio)butanoateChEBI
9cis,12cis-OctadecadienoylcarnitineChEBI
LinoleylcarnitineChEBI
3-[(9Z,12Z)-Octadeca-9,12-dienoyloxy]-4-(trimethylammonio)butanoic acidGenerator
Chemical FormulaC25H45NO4
Average Molecular Weight423.638
Monoisotopic Molecular Weight423.334858933
IUPAC Name3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-4-(trimethylazaniumyl)butanoate
Traditional Namelinoelaidyl carnitine
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])CCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C25H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-25(29)30-23(21-24(27)28)22-26(2,3)4/h9-10,12-13,23H,5-8,11,14-22H2,1-4H3/b10-9-,13-12-
InChI KeyMJLXQSQYKZWZCB-UTJQPWESSA-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
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP1.46ALOGPS
logP2.2ChemAxon
logS-7.7ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity148.51 m³·mol⁻¹ChemAxon
Polarizability51.26 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+216.08530932474
DeepCCS[M-H]-213.6930932474
DeepCCS[M-2H]-246.57430932474
DeepCCS[M+Na]+221.99830932474
AllCCS[M+H]+219.032859911
AllCCS[M+H-H2O]+217.232859911
AllCCS[M+NH4]+220.732859911
AllCCS[M+Na]+221.232859911
AllCCS[M-H]-211.232859911
AllCCS[M+Na-2H]-213.632859911
AllCCS[M+HCOO]-216.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
O-Linoleoylcarnitine[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])CCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C3464.9Standard polar33892256
O-Linoleoylcarnitine[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])CCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C2560.4Standard non polar33892256
O-Linoleoylcarnitine[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])CCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C2895.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - O-Linoleoylcarnitine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - O-Linoleoylcarnitine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Linoleoylcarnitine 10V, Positive-QTOFsplash10-00di-0000900000-013b520638a6f6e841ef2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Linoleoylcarnitine 20V, Positive-QTOFsplash10-0079-9000500000-f8699786d83873f3e7b32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Linoleoylcarnitine 40V, Positive-QTOFsplash10-000i-9000000000-e9262cbaff8cb4ad0ba62021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID28639188
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound51000598
PDB IDNot Available
ChEBI ID73072
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Iacobazzi V, Pasquali M, Singh R, Matern D, Rinaldo P, Amat di San Filippo C, Palmieri F, Longo N: Response to therapy in carnitine/acylcarnitine translocase (CACT) deficiency due to a novel missense mutation. Am J Med Genet A. 2004 Apr 15;126A(2):150-5. [PubMed:15057979 ]
  2. Sud M, Fahy E, Cotter D, Brown A, Dennis EA, Glass CK, Merrill AH Jr, Murphy RC, Raetz CR, Russell DW, Subramaniam S: LMSD: LIPID MAPS structure database. Nucleic Acids Res. 2007 Jan;35(Database issue):D527-32. doi: 10.1093/nar/gkl838. Epub 2006 Nov 10. [PubMed:17098933 ]
  3. 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. [PubMed:13825279 ]
  4. 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. [PubMed:22804748 ]
  5. 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. [PubMed:19073774 ]
  6. 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. [PubMed:23258903 ]
  7. 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. [PubMed:26796394 ]
  8. Hunter WG, Kelly JP, McGarrah RW 3rd, Khouri MG, Craig D, Haynes C, Ilkayeva O, Stevens RD, Bain JR, Muehlbauer MJ, Newgard CB, Felker GM, Hernandez AF, Velazquez EJ, Kraus WE, Shah SH: Metabolomic Profiling Identifies Novel Circulating Biomarkers of Mitochondrial Dysfunction Differentially Elevated in Heart Failure With Preserved Versus Reduced Ejection Fraction: Evidence for Shared Metabolic Impairments in Clinical Heart Failure. J Am Heart Assoc. 2016 Jul 29;5(8). pii: JAHA.115.003190. doi: 10.1161/JAHA.115.003190. [PubMed:27473038 ]
  9. Liepinsh E, Makrecka-Kuka M, Volska K, Kuka J, Makarova E, Antone U, Sevostjanovs E, Vilskersts R, Strods A, Tars K, Dambrova M: Long-chain acylcarnitines determine ischaemia/reperfusion-induced damage in heart mitochondria. Biochem J. 2016 May 1;473(9):1191-202. doi: 10.1042/BCJ20160164. Epub 2016 Mar 2. [PubMed:26936967 ]
  10. Shah SH, Sun JL, Stevens RD, Bain JR, Muehlbauer MJ, Pieper KS, Haynes C, Hauser ER, Kraus WE, Granger CB, Newgard CB, Califf RM, Newby LK: Baseline metabolomic profiles predict cardiovascular events in patients at risk for coronary artery disease. Am Heart J. 2012 May;163(5):844-850.e1. doi: 10.1016/j.ahj.2012.02.005. [PubMed:22607863 ]
  11. Rizza S, Copetti M, Rossi C, Cianfarani MA, Zucchelli M, Luzi A, Pecchioli C, Porzio O, Di Cola G, Urbani A, Pellegrini F, Federici M: Metabolomics signature improves the prediction of cardiovascular events in elderly subjects. Atherosclerosis. 2014 Feb;232(2):260-4. doi: 10.1016/j.atherosclerosis.2013.10.029. Epub 2013 Nov 18. [PubMed:24468136 ]
  12. Chang KH, Cheng ML, Tang HY, Huang CY, Wu YR, Chen CM: Alternations of Metabolic Profile and Kynurenine Metabolism in the Plasma of Parkinson's Disease. Mol Neurobiol. 2018 Aug;55(8):6319-6328. doi: 10.1007/s12035-017-0845-3. Epub 2018 Jan 2. [PubMed:29294246 ]
  13. Dambrova M, Makrecka-Kuka M, Kuka J, Vilskersts R, Nordberg D, Attwood MM, Smesny S, Sen ZD, Guo AC, Oler E, Tian S, Zheng J, Wishart DS, Liepinsh E, Schioth HB: Acylcarnitines: Nomenclature, Biomarkers, Therapeutic Potential, Drug Targets, and Clinical Trials. Pharmacol Rev. 2022 Jul;74(3):506-551. doi: 10.1124/pharmrev.121.000408. [PubMed:35710135 ]