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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-05-23 00:16:52 UTC
Update Date2022-03-07 02:49:31 UTC
HMDB IDHMDB0006318
Secondary Accession Numbers
  • HMDB06318
Metabolite Identification
Common NameGamma-linolenyl carnitine
Descriptiongamma-linolenyl carnitine is an acylcarnitine. Numerous disorders have been described that lead to disturbances in energy production and in intermediary metabolism in the organism which are characterized by the production and excretion of unusual acylcarnitines. A mutation in the gene coding for carnitine-acylcarnitine translocase or the OCTN2 transporter aetiologically causes a carnitine deficiency that results in poor intestinal absorption of dietary L-carnitine, its impaired reabsorption by the kidney and, consequently, in increased urinary loss of L-carnitine. Determination of the qualitative pattern of acylcarnitines can be of diagnostic and therapeutic importance. The betaine structure of carnitine requires special analytical procedures for recording. The ionic nature of L-carnitine causes a high water solubility which decreases with increasing chain length of the ester group in the acylcarnitines. Therefore, the distribution of L-carnitine and acylcarnitines in various organs is defined by their function and their physico-chemical properties as well. High performance liquid chromatography (HPLC) permits screening for free and total carnitine, as well as complete quantitative acylcarnitine determination, including the long-chain acylcarnitine profile. (PMID: 17508264 , Monatshefte fuer Chemie (2005), 136(8), 1279-1291., Int J Mass Spectrom. 1999;188:39-52.).
Structure
Data?1582752380
Synonyms
ValueSource
g-Linolenyl carnitineGenerator
Γ-linolenyl carnitineGenerator
Chemical FormulaC25H43NO4
Average Molecular Weight421.622
Monoisotopic Molecular Weight421.319208869
IUPAC Name(3S)-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-4-(trimethylazaniumyl)butanoate
Traditional Name(3S)-3-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoyloxy]-4-(trimethylammonio)butanoate
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/C\C=C/CCCCC(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C25H43NO4/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/h9-10,12-13,15-16,23H,5-8,11,14,17-22H2,1-4H3/b10-9-,13-12-,16-15-/t23-/m0/s1
InChI KeyYCINYVPLUUGAJO-BAHSRKMSSA-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 salt
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
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 Solubility1.4e-05 g/LALOGPS
logP1.2ALOGPS
logP1.84ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)4.26ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity149.63 m³·mol⁻¹ChemAxon
Polarizability49.76 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]+231.14730932474
DeepCCS[M-H]-227.88730932474
DeepCCS[M-2H]-262.14130932474
DeepCCS[M+Na]+238.64430932474
AllCCS[M+H]+217.132859911
AllCCS[M+H-H2O]+215.232859911
AllCCS[M+NH4]+218.832859911
AllCCS[M+Na]+219.332859911
AllCCS[M-H]-209.632859911
AllCCS[M+Na-2H]-212.032859911
AllCCS[M+HCOO]-214.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Gamma-linolenyl carnitineCCCCC\C=C/C\C=C/C\C=C/CCCCC(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C3453.1Standard polar33892256
Gamma-linolenyl carnitineCCCCC\C=C/C\C=C/C\C=C/CCCCC(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C2581.9Standard non polar33892256
Gamma-linolenyl carnitineCCCCC\C=C/C\C=C/C\C=C/CCCCC(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C2857.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Gamma-linolenyl carnitine 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 - Gamma-linolenyl carnitine 10V, Positive-QTOFsplash10-0h2f-0953800000-b7f63b2e26512e434b532019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-linolenyl carnitine 20V, Positive-QTOFsplash10-0006-1920000000-db39d2cd8d518b79098b2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-linolenyl carnitine 40V, Positive-QTOFsplash10-0006-4940000000-9e893491acdc070aff032019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-linolenyl carnitine 10V, Negative-QTOFsplash10-00di-1031900000-f32b57f41e39f3637d192019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-linolenyl carnitine 20V, Negative-QTOFsplash10-08or-1189400000-0f190d6f4cba56a454e42019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-linolenyl carnitine 40V, Negative-QTOFsplash10-0a7l-5190000000-87f6e29333fb380916772019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-linolenyl carnitine 10V, Positive-QTOFsplash10-00di-0000900000-5b8e47c72031be6728442021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-linolenyl carnitine 20V, Positive-QTOFsplash10-0079-9000500000-538e3c7c8dad45a2f01e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-linolenyl carnitine 40V, Positive-QTOFsplash10-000i-9000000000-e9262cbaff8cb4ad0ba62021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023885
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2614408
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477819
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDLNLNCGCRN
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pierre G, Macdonald A, Gray G, Hendriksz C, Preece MA, Chakrapani A: Prospective treatment in carnitine-acylcarnitine translocase deficiency. J Inherit Metab Dis. 2007 Oct;30(5):815. Epub 2007 May 12. [PubMed:17508264 ]