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Record Information
Version5.0
StatusPredicted
Creation Date2021-03-31 19:22:28 UTC
Update Date2021-09-14 14:58:18 UTC
HMDB IDHMDB0241618
Secondary Accession NumbersNone
Metabolite Identification
Common Name(4Z,7E,9E,13Z,16Z,19Z)-11-Hydroxydocosa-4,7,9,13,16,19-hexaenoylcarnitine
Description(4Z,7E,9E,13Z,16Z,19Z)-11-hydroxydocosa-4,7,9,13,16,19-hexaenoylcarnitine is an acylcarnitine. More specifically, it is an (4Z,7E,9E,13Z,16Z,19Z)-11-hydroxydocosa-4,7,9,13,16,19-hexaenoic 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 [Dambrova et al. 2021, Physiological Reviews], 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. (4Z,7E,9E,13Z,16Z,19Z)-11-hydroxydocosa-4,7,9,13,16,19-hexaenoylcarnitine is therefore classified as a very-long chain AC. As a very long-chain acylcarnitine (4Z,7E,9E,13Z,16Z,19Z)-11-hydroxydocosa-4,7,9,13,16,19-hexaenoylcarnitine is generally formed in the cytoplasm from very long acyl groups synthesized by fatty acid synthases or obtained from the diet. Very-long-chain fatty acids are generally too long to be involved in mitochondrial beta-oxidation. As a result peroxisomes are the main organelle where very-long-chain fatty acids are metabolized and their acylcarnitines synthesized (PMID: 18793625 ). Altered levels of very long-chain acylcarnitines can serve as useful markers for inherited disorders of peroxisomal metabolism. 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 at [Dambrova et al. 2021, Physiological Reviews].
Structure
Data?1621497875
SynonymsNot Available
Chemical FormulaC29H45NO5
Average Molecular Weight487.681
Monoisotopic Molecular Weight487.329773553
IUPAC Name3-[(11-hydroxydocosa-4,7,9,13,16,19-hexaenoyl)oxy]-4-(trimethylazaniumyl)butanoate
Traditional Name3-[(11-hydroxydocosa-4,7,9,13,16,19-hexaenoyl)oxy]-4-(trimethylammonio)butanoate
CAS Registry NumberNot Available
SMILES
CCC=CCC=CCC=CCC(O)C=CC=CCC=CCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C29H45NO5/c1-5-6-7-8-9-10-12-15-18-21-26(31)22-19-16-13-11-14-17-20-23-29(34)35-27(24-28(32)33)25-30(2,3)4/h6-7,9-10,13-19,22,26-27,31H,5,8,11-12,20-21,23-25H2,1-4H3
InChI KeyBQGUWWTWHRBLTA-UHFFFAOYSA-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
  • Secondary alcohol
  • Carboxylic acid salt
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organic zwitterion
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10(1.3) g/LChemAxon
pKa (Strongest Acidic)4.17ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area86.66 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity172.9 m³·mol⁻¹ChemAxon
Polarizability57.78 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(4Z,7E,9E,13Z,16Z,19Z)-11-Hydroxydocosa-4,7,9,13,16,19-hexaenoylcarnitine,1TMS,#1CCC=CCC=CCC=CCC(C=CC=CCC=CCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C3502.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
(4Z,7E,9E,13Z,16Z,19Z)-11-Hydroxydocosa-4,7,9,13,16,19-hexaenoylcarnitine,1TBDMS,#1CCC=CCC=CCC=CCC(C=CC=CCC=CCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C)O[Si](C)(C)C(C)(C)C3723.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (4Z,7E,9E,13Z,16Z,19Z)-11-Hydroxydocosa-4,7,9,13,16,19-hexaenoylcarnitine 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 - (4Z,7E,9E,13Z,16Z,19Z)-11-Hydroxydocosa-4,7,9,13,16,19-hexaenoylcarnitine 10V, Positive-QTOFNot Available2021-04-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z,7E,9E,13Z,16Z,19Z)-11-Hydroxydocosa-4,7,9,13,16,19-hexaenoylcarnitine 20V, Positive-QTOFNot Available2021-04-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z,7E,9E,13Z,16Z,19Z)-11-Hydroxydocosa-4,7,9,13,16,19-hexaenoylcarnitine 40V, Positive-QTOFNot Available2021-04-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z,7E,9E,13Z,16Z,19Z)-11-Hydroxydocosa-4,7,9,13,16,19-hexaenoylcarnitine 10V, Positive-QTOFsplash10-000i-0000900000-ee01cc9607e26ee369d22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z,7E,9E,13Z,16Z,19Z)-11-Hydroxydocosa-4,7,9,13,16,19-hexaenoylcarnitine 20V, Positive-QTOFsplash10-000i-9000500000-d7223ee2ee4c176870502021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z,7E,9E,13Z,16Z,19Z)-11-Hydroxydocosa-4,7,9,13,16,19-hexaenoylcarnitine 40V, Positive-QTOFsplash10-000i-9000000000-e9262cbaff8cb4ad0ba62021-09-23Wishart 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 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
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Blazenovic I, Kind T, Sa MR, Ji J, Vaniya A, Wancewicz B, Roberts BS, Torbasinovic H, Lee T, Mehta SS, Showalter MR, Song H, Kwok J, Jahn D, Kim J, Fiehn O: Structure Annotation of All Mass Spectra in Untargeted Metabolomics. Anal Chem. 2019 Feb 5;91(3):2155-2162. doi: 10.1021/acs.analchem.8b04698. Epub 2019 Jan 16. [PubMed:30608141 ]
  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. Duranti G, Boenzi S, Rizzo C, Rava L, Di Ciommo V, Carrozzo R, Meschini MC, Johnson DW, Dionisi-Vici C: Urine acylcarnitine analysis by ESI-MS/MS: a new tool for the diagnosis of peroxisomal biogenesis disorders. Clin Chim Acta. 2008 Dec;398(1-2):86-9. doi: 10.1016/j.cca.2008.08.018. Epub 2008 Aug 28. [PubMed:18793625 ]
  4. Yu D, Zhou L, Xuan Q, Wang L, Zhao X, Lu X, Xu G: Strategy for Comprehensive Identification of Acylcarnitines Based on Liquid Chromatography-High-Resolution Mass Spectrometry. Anal Chem. 2018 May 1;90(9):5712-5718. doi: 10.1021/acs.analchem.7b05471. Epub 2018 Apr 20. [PubMed:29651844 ]
  5. Yan X, Markey SP, Marupaka R, Dong Q, Cooper BT, Mirokhin YA, Wallace WE, Stein SE: Mass Spectral Library of Acylcarnitines Derived from Human Urine. Anal Chem. 2020 May 5;92(9):6521-6528. doi: 10.1021/acs.analchem.0c00129. Epub 2020 Apr 23. [PubMed:32271007 ]
  6. Zuniga A, Li L: Ultra-high performance liquid chromatography tandem mass spectrometry for comprehensive analysis of urinary acylcarnitines. Anal Chim Acta. 2011 Mar 9;689(1):77-84. doi: 10.1016/j.aca.2011.01.018. Epub 2011 Jan 18. [PubMed:21338760 ]