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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-02-24 01:45:01 UTC
Update Date2022-10-24 19:44:16 UTC
HMDB IDHMDB0240761
Secondary Accession NumbersNone
Metabolite Identification
Common Name(9Z)-3-Hydroxyoctadecenoylcarnitine
Description(9Z)-3-Hydroxyoctadecenoylcarnitine is an acylcarnitine. More specifically, it is an (9Z)-hydroxyoctadec-9-enoic 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. (9Z)-3-Hydroxyoctadecenoylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine (9Z)-3-Hydroxyoctadecenoylcarnitine 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 (9Z)-3-Hydroxyoctadecenoylcarnitine is elevated in the blood or plasma of individuals with chronic fatigue syndrome (PMID: 21205027 ), mitochondrial trifunctional protein deficiency (PMID: 19880769 ), and psoriasis (PMID: 33391503 ). 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
3-HydroxyoleoylcarnitineChEBI
3-{[(9Z)-3-hydroxyoctadec-9-enoyl]oxy}-4-(trimethylammonio)butanoateChEBI
9-cis-3-HydroxyoctadecenoylcarnitineChEBI
3-{[(9Z)-3-hydroxyoctadec-9-enoyl]oxy}-4-(trimethylammonio)butanoic acidGenerator
Chemical FormulaC25H47NO5
Average Molecular Weight441.653
Monoisotopic Molecular Weight441.345423617
IUPAC Name3-{[(9Z)-3-hydroxyoctadec-9-enoyl]oxy}-4-(trimethylazaniumyl)butanoate
Traditional Name3-{[(9Z)-3-hydroxyoctadec-9-enoyl]oxy}-4-(trimethylammonio)butanoate
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCCCCC)=C(/[H])CCCCCC(O)CC(=O)OC(CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C25H47NO5/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-22(27)19-25(30)31-23(20-24(28)29)21-26(2,3)4/h12-13,22-23,27H,5-11,14-21H2,1-4H3/b13-12-
InChI KeyYBCVTTMMURGSEY-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
  • Beta-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic zwitterion
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Alcohol
  • 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
logP0.41ALOGPS
logP1.33ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)4.1ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area86.66 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity148.91 m³·mol⁻¹ChemAxon
Polarizability53.28 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]+237.78730932474
DeepCCS[M-H]-234.52730932474
DeepCCS[M-2H]-268.78230932474
DeepCCS[M+Na]+245.28430932474
AllCCS[M+H]+224.432859911
AllCCS[M+H-H2O]+222.732859911
AllCCS[M+NH4]+226.032859911
AllCCS[M+Na]+226.432859911
AllCCS[M-H]-216.232859911
AllCCS[M+Na-2H]-218.532859911
AllCCS[M+HCOO]-221.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(9Z)-3-Hydroxyoctadecenoylcarnitine[H]\C(CCCCCCCC)=C(/[H])CCCCCC(O)CC(=O)OC(CC([O-])=O)C[N+](C)(C)C3427.3Standard polar33892256
(9Z)-3-Hydroxyoctadecenoylcarnitine[H]\C(CCCCCCCC)=C(/[H])CCCCCC(O)CC(=O)OC(CC([O-])=O)C[N+](C)(C)C2728.2Standard non polar33892256
(9Z)-3-Hydroxyoctadecenoylcarnitine[H]\C(CCCCCCCC)=C(/[H])CCCCCC(O)CC(=O)OC(CC([O-])=O)C[N+](C)(C)C3058.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(9Z)-3-Hydroxyoctadecenoylcarnitine,1TMS,isomer #1CCCCCCCC/C=C\CCCCCC(CC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C3013.0Semi standard non polar33892256
(9Z)-3-Hydroxyoctadecenoylcarnitine,1TBDMS,isomer #1CCCCCCCC/C=C\CCCCCC(CC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C3226.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (9Z)-3-Hydroxyoctadecenoylcarnitine 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 - (9Z)-3-Hydroxyoctadecenoylcarnitine 10V, Positive-QTOFsplash10-0006-0000900000-7db28d14eecb798f08e82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9Z)-3-Hydroxyoctadecenoylcarnitine 20V, Positive-QTOFsplash10-000l-9000500000-829de551551958c8e9e42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9Z)-3-Hydroxyoctadecenoylcarnitine 40V, Positive-QTOFsplash10-000i-9000000000-e9262cbaff8cb4ad0ba62021-09-24Wishart 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 ID28639190
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID73076
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. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. Chen C, Hou G, Zeng C, Ren Y, Chen X, Peng C: Metabolomic profiling reveals amino acid and carnitine alterations as metabolic signatures in psoriasis. Theranostics. 2021 Jan 1;11(2):754-767. doi: 10.7150/thno.51154. eCollection 2021. [PubMed:33391503 ]
  8. Park HD, Kim SR, Ki CS, Lee SY, Chang YS, Jin DK, Park WS: Two novel HADHB gene mutations in a Korean patient with mitochondrial trifunctional protein deficiency. Ann Clin Lab Sci. 2009 Fall;39(4):399-404. [PubMed:19880769 ]
  9. Reuter SE, Evans AM: Long-chain acylcarnitine deficiency in patients with chronic fatigue syndrome. Potential involvement of altered carnitine palmitoyltransferase-I activity. J Intern Med. 2011 Jul;270(1):76-84. doi: 10.1111/j.1365-2796.2010.02341.x. Epub 2011 Jan 19. [PubMed:21205027 ]
  10. 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 ]