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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-05-23 10:07:09 UTC
Update Date2022-03-07 02:49:31 UTC
HMDB IDHMDB0006460
Secondary Accession Numbers
  • HMDB06460
Metabolite Identification
Common NameArachidyl carnitine
DescriptionArachidyl 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?1582752384
Synonyms
ValueSource
3-(Icosanoyloxy)-4-(trimethylammonio)butanoateChEBI
ArachidoylcarnitineChEBI
EicosanoylcarnitineChEBI
IcosanoylcarnitineChEBI
O-ArachidoylcarnitineChEBI
O-EicosanoylcarnitineChEBI
3-(Icosanoyloxy)-4-(trimethylammonio)butanoic acidGenerator
O-IcosanoylcarnitineChEBI, HMDB
Chemical FormulaC27H53NO4
Average Molecular Weight455.714
Monoisotopic Molecular Weight455.397459189
IUPAC Name3-(icosanoyloxy)-4-(trimethylazaniumyl)butanoate
Traditional Namearachidyl carnitine
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C27H53NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-27(31)32-25(23-26(29)30)24-28(2,3)4/h25H,5-24H2,1-4H3
InChI KeySVJLJQBGUITFLI-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
  • 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
Biological locationRoute of exposureSource
Process
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 Solubility9.3e-06 g/LALOGPS
logP3.37ALOGPS
logP3.81ChemAxon
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 Count24ChemAxon
Refractivity155.48 m³·mol⁻¹ChemAxon
Polarizability58.87 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]+220.75730932474
DeepCCS[M-H]-216.73830932474
DeepCCS[M-2H]-253.2830932474
DeepCCS[M+Na]+229.57330932474
AllCCS[M+H]+235.232859911
AllCCS[M+H-H2O]+233.632859911
AllCCS[M+NH4]+236.632859911
AllCCS[M+Na]+237.032859911
AllCCS[M-H]-223.532859911
AllCCS[M+Na-2H]-225.732859911
AllCCS[M+HCOO]-228.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Arachidyl carnitineCCCCCCCCCCCCCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C3328.0Standard polar33892256
Arachidyl carnitineCCCCCCCCCCCCCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C2858.0Standard non polar33892256
Arachidyl carnitineCCCCCCCCCCCCCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C3106.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Arachidyl carnitine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9230000000-d003e9fb89960a91f1c32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Arachidyl 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 - Arachidyl carnitine 10V, Positive-QTOFsplash10-0btm-0741900000-982878cdba41298de5c92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arachidyl carnitine 20V, Positive-QTOFsplash10-0f6x-1920000000-93b92e630bffe70fb3152017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arachidyl carnitine 40V, Positive-QTOFsplash10-0f6x-5950000000-fa562032a654105d1af22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arachidyl carnitine 10V, Negative-QTOFsplash10-0udi-1013900000-691af6e2b7cccf3f992d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arachidyl carnitine 20V, Negative-QTOFsplash10-0udj-1139300000-8d0e1add6ba177dea3e92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arachidyl carnitine 40V, Negative-QTOFsplash10-0006-6195000000-fac5044984c6891e7e412017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arachidyl carnitine 10V, Positive-QTOFsplash10-0a4i-0000900000-a6536ad39d4c1c0261382021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arachidyl carnitine 20V, Positive-QTOFsplash10-052r-9000500000-39f7cd70255e0f7c49c22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arachidyl carnitine 40V, Positive-QTOFsplash10-000i-9000000000-e9262cbaff8cb4ad0ba62021-09-25Wishart 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 IDFDB023920
KNApSAcK IDNot Available
Chemspider ID28639199
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2614347
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477833
PDB IDNot Available
ChEBI ID73100
Food Biomarker OntologyNot Available
VMH IDARACHCRN
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 ]