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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-10-23 13:06:02 UTC
Update Date2022-10-24 19:44:11 UTC
HMDB IDHMDB0005065
Secondary Accession Numbers
  • HMDB0062772
  • HMDB05065
  • HMDB62772
Metabolite Identification
Common NameOleoylcarnitine
DescriptionOleoylcarnitine is an acylcarnitine. More specifically, it is an oleic acid 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. Oleoylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine oleoylcarnitine 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 oleoylcarnitine is elevated in the blood or plasma of individuals with carnitine palmitoyl transferase 2 deficiency (PMID: 15653102 , PMID: 11999976 ), cardiovascular mortality in incident dialysis patients (PMID: 24308938 ), schizophrenia (PMID: 31161852 ), succinic semialdehyde dehydrogenase deficiency (PMID: 32967698 ), neonatal macrosomia (PMID: 32126138 ), liver cirrhosis (PMID: 32075591 ), CPT II deficiency (PMID: 28801073 , PMID: 18987586 , PMID: 18925671 , PMID: 11585077 ), 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
Data?1614288046
Synonyms
ValueSource
(9Z)-Octadecenoyl-L-carnitineChEBI
(R)-[(9Z)-Octadecenoyl]carnitineChEBI
Acylcarnitine C18:1ChEBI
O-(9Z)-Octadecenoyl-(R)-carnitineChEBI
Oleoyl-L-carnitineChEBI
(Z)-(+-)-3-Carboxy-N,N,N-trimethyl-2-((1-oxo-9-octadecenyl)oxy)-1-propanaminiumHMDB
Oleoylcarnitine, (R-(Z))-isomerHMDB
O-OleoylcarnitineHMDB
(9Z)-Octadec-9-enoylcarnitineHMDB
cis-9-OctadecenoylcarnitineHMDB
(R)-OleoylcarnitineHMDB
OleoylcarnitineChEBI
Chemical FormulaC25H48NO4
Average Molecular Weight426.661
Monoisotopic Molecular Weight426.35778545
IUPAC Name(3R)-3-[(9Z)-octadec-9-enoyloxy]-4-(trimethylazaniumyl)butanoate
Traditional Name(3R)-3-[(9Z)-octadec-9-enoyloxy]-4-(trimethylammonio)butanoate
CAS Registry Number38677-66-6
SMILES
CCCCCCCC\C=C/CCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C25H47NO4/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/h12-13,23H,5-11,14-22H2,1-4H3/p+1/b13-12-/t23-/m1/s1
InChI KeyIPOLTUVFXFHAHI-WHIOSMTNSA-O
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
Not AvailableNot Available
Physical Properties
StateSolid
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
Water Solubility6.7e-06 g/LALOGPS
logP2.02ALOGPS
logP2.56ChemAxon
logS-7.9ALOGPS
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 Count21ChemAxon
Refractivity147.4 m³·mol⁻¹ChemAxon
Polarizability53.07 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]+221.95730932474
DeepCCS[M-H]-217.93730932474
DeepCCS[M-2H]-254.4830932474
DeepCCS[M+Na]+230.77230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OleoylcarnitineCCCCCCCC\C=C/CCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C3623.7Standard polar33892256
OleoylcarnitineCCCCCCCC\C=C/CCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C2640.9Standard non polar33892256
OleoylcarnitineCCCCCCCC\C=C/CCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C2954.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Oleoylcarnitine,1TMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C)C[N+](C)(C)C2969.3Semi standard non polar33892256
Oleoylcarnitine,1TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C[N+](C)(C)C3198.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Oleoylcarnitine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oleoylcarnitine 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 - Oleoylcarnitine 10V, Positive-QTOFsplash10-004i-0000900000-c76c8c1a67e6b24de5c12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoylcarnitine 20V, Positive-QTOFsplash10-002r-9000500000-4902a8769b2895518a152021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleoylcarnitine 40V, Positive-QTOFsplash10-000i-9000000000-e9262cbaff8cb4ad0ba62021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.040-0.210 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.11 (0.08-0.15) uMNewborn (0-30 days old)Not Available
Normal
details
BloodDetected and Quantified0.87 +/- 0.58 uMChildren (1-13 years old)Both
Normal
details
BloodDetected and Quantified0.20 +/- 0.28 uMChildren (1-13 years old)Both
Normal
details
BloodDetected and Quantified0.17 (0.14-0.26) uMInfant (0-1 year old)Not Available
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.64 +/- 0.49 uMChildren (1-13 years old)Both
Acetaminophen overdose
details
BloodDetected and Quantified0.107 +/- 0.038 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified0.111 +/- 0.039 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Obesity
  1. Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023614
KNApSAcK IDNot Available
Chemspider ID21403150
KEGG Compound IDNot Available
BioCyc IDCPD-20402
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound46907933
PDB IDNot Available
ChEBI ID84651
Food Biomarker OntologyNot Available
VMH IDODECRN
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
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  2. Minkler PE, Kerner J, North KN, Hoppel CL: Quantitation of long-chain acylcarnitines by HPLC/fluorescence detection: application to plasma and tissue specimens from patients with carnitine palmitoyltransferase-II deficiency. Clin Chim Acta. 2005 Feb;352(1-2):81-92. [PubMed:15653102 ]
  3. Gempel K, Kiechl S, Hofmann S, Lochmuller H, Kiechl-Kohlendorfer U, Willeit J, Sperl W, Rettinger A, Bieger I, Pongratz D, Gerbitz KD, Bauer MF: Screening for carnitine palmitoyltransferase II deficiency by tandem mass spectrometry. J Inherit Metab Dis. 2002 Feb;25(1):17-27. [PubMed:11999976 ]
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  6. 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 ]
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  13. 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 ]
  14. Cao B, Wang D, Pan Z, McIntyre RS, Brietzke E, Subramanieapillai M, Nozari Y, Wang J: Metabolic profiling for water-soluble metabolites in patients with schizophrenia and healthy controls in a Chinese population: A case-control study. World J Biol Psychiatry. 2020 Jun;21(5):357-367. doi: 10.1080/15622975.2019.1615639. Epub 2019 Jun 4. [PubMed:31161852 ]
  15. Kalim S, Clish CB, Wenger J, Elmariah S, Yeh RW, Deferio JJ, Pierce K, Deik A, Gerszten RE, Thadhani R, Rhee EP: A plasma long-chain acylcarnitine predicts cardiovascular mortality in incident dialysis patients. J Am Heart Assoc. 2013 Dec 5;2(6):e000542. doi: 10.1161/JAHA.113.000542. [PubMed:24308938 ]
  16. Kirby T, Walters DC, Shi X, Turgeon C, Rinaldo P, Arning E, Ashcraft P, Bottiglieri T, DiBacco M, Pearl PL, Roullet JB, Gibson KM: Novel biomarkers and age-related metabolite correlations in plasma and dried blood spots from patients with succinic semialdehyde dehydrogenase deficiency. Orphanet J Rare Dis. 2020 Sep 23;15(1):261. doi: 10.1186/s13023-020-01522-5. [PubMed:32967698 ]
  17. Wright EL, Baker PR: Neonatal Macrosomia is an Interfering Factor for Analytes on the Colorado State Newborn Screen. J Clin Endocrinol Metab. 2020 Mar 1;105(3). pii: 5775549. doi: 10.1210/clinem/dgz183. [PubMed:32126138 ]
  18. Miyaaki H, Kobayashi H, Miuma S, Fukusima M, Sasaki R, Haraguchi M, Nakao K: Blood carnitine profiling on tandem mass spectrometry in liver cirrhotic patients. BMC Gastroenterol. 2020 Feb 19;20(1):41. doi: 10.1186/s12876-020-01190-6. [PubMed:32075591 ]
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  20. Brucknerova I, Bzduch V, Behulova D, Ferianec V, Dubovicky M, Ujhazy E, Mach M: Reversible asphyxial status in a newborn due to neonatal form of carnitine palmitoyltransferase II deficiency. Neuro Endocrinol Lett. 2008 Oct;29(5):627-30. [PubMed:18987586 ]
  21. Illsinger S, Lucke T, Peter M, Ruiter JP, Wanders RJ, Deschauer M, Handig I, Wuyts W, Das AM: Carnitine-palmitoyltransferase 2 deficiency: novel mutations and relevance of newborn screening. Am J Med Genet A. 2008 Nov 15;146A(22):2925-8. doi: 10.1002/ajmg.a.32545. [PubMed:18925671 ]
  22. Gempel K, von Praun C, Baumkotter J, Lehnert W, Ensenauer R, Gerbitz KD, Bauer MF: "Adult" form of muscular carnitine palmitoyltransferase II deficiency: manifestation in a 2-year-old child. Eur J Pediatr. 2001 Sep;160(9):548-51. doi: 10.1007/s004310100802. [PubMed:11585077 ]
  23. 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 ]
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