Record Information
Version1.0
Creation date2011-09-21 00:36:52 UTC
Update date2015-07-21 06:57:56 UTC
Primary IDFDB023921
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLinoelaidyl carnitine
DescriptionLinoelaidyl 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.) [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
3-[(9E,12E)-Octadeca-9,12-dienoyloxy]-4-(trimethylammonio)butanoateChEBI
Acylcarnitine C18:2ChEBI
3-[(9E,12E)-Octadeca-9,12-dienoyloxy]-4-(trimethylammonio)butanoic acidGenerator
C18:2 CarnitineHMDB
L-LinoleoylcarnitineHMDB
Linoelaidyl carnitineHMDB
LinoleoylcarnitineHMDB
LinoleylcarnitineHMDB
O-LinoelaidylcarnitineHMDB
3-[(9e,12e)-Octadeca-9,12-dienoyloxy]-4-(trimethylammonio)butanoateChEBI
3-[(9e,12e)-Octadeca-9,12-dienoyloxy]-4-(trimethylammonio)butanoic acidGenerator
acylcarnitine C18:2hmdb
Predicted Properties
PropertyValueSource
Water Solubility8.6e-06 g/LALOGPS
logP1.46ALOGPS
logP2.2ChemAxon
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 Count20ChemAxon
Refractivity148.51 m³·mol⁻¹ChemAxon
Polarizability51.16 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC25H45NO4
IUPAC name3-[(9E,12E)-octadeca-9,12-dienoyloxy]-4-(trimethylazaniumyl)butanoate
InChI IdentifierInChI=1S/C25H45NO4/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/h9-10,12-13,23H,5-8,11,14-22H2,1-4H3/b10-9+,13-12+
InChI KeyMJLXQSQYKZWZCB-OKLKQMLOSA-N
Isomeric SMILESCCCCC\C=C\C\C=C\CCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C
Average Molecular Weight423.6291
Monoisotopic Molecular Weight423.334858933
Classification
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-9230000000-8e303f952de7b09a4059JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-074l-0953800000-c042c48279e03c6942ddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-1920000000-23f60e51d007ae34b3c8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-4930000000-838683bf758f3bdc0bfdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1031900000-9dae0fd9ea2fd4d9a94aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03k9-1179400000-b3c183368ca837a1abb3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06vu-5090000000-1b5b91637ffacc86b31fJSpectraViewer
ChemSpider ID28540387
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53477834
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06461
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID2614390
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference