Showing metabocard for Stearoylcarnitine (LMDB00260)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:45:54 UTC
Update Date2020-03-13 18:12:33 UTC
LmdbLMDB00260
Secondary Accession NumbersNone
Metabolite Identification
Common NameStearoylcarnitine
DescriptionStearoylcarnitine is found in significantly greater amounts of lpatients with carnitine palmitoyltransferase (CPT) II deficiency when compared to controls. ( PubMed ID 15653102 ). The carnitine palmitoyltransferase (CPT; EC 2.3.1.21) enzyme system, in conjunction with acyl-CoA synthetase and carnitine/acylcarnitine translocase (212138), provides the mechanism whereby long-chain fatty acids are transferred from the cytosol to the mitochondrial matrix to undergo beta-oxidation. (OMIM 600650 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-StearoylcarnitineChEBI
(R)-OctadecanoylcarnitineChEBI
(R)-StearoylcarnitineChEBI
Acylcarnitine C18:0ChEBI
L-StearoylcarnitineChEBI
O-Octadecanoyl-(R)-carnitineChEBI
O-Octadecanoyl-R-carnitineChEBI
O-Stearoyl-L-carnitineChEBI
OctadecanoylcarnitineChEBI
3-(Octadecanoyloxy)-4-(trimethylammonio)butanoateHMDB
O-OctadecanoylcarnitineHMDB
3-(Octadecanoyloxy)-4-(trimethylammonio)butanoic acidHMDB
(R)-3-Carboxy-N,N,N-trimethyl-2-[(1-oxooctadecyl)oxy]-1-propanaminium inner saltHMDB
L-(3-Carboxy-2-hydroxypropyl)trimethyl-ammonium stearate hydroxide inner saltHMDB
L-Stearic acid ester with (3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner saltHMDB
Octadecanoyl-L-carnitineHMDB
Stearoyl-L-carnitineHMDB
StearoylcarnitineChEBI
Chemical FormulaC25H49NO4
Average Molecular Weight427.6609
Monoisotopic Molecular Weight427.366159061
IUPAC Name(3R)-3-(octadecanoyloxy)-4-(trimethylazaniumyl)butanoate
Traditional Namestearoylcarnitine
CAS Registry Number1976-27-8
SMILES
CCCCCCCCCCCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C25H49NO4/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/h23H,5-22H2,1-4H3
InChI KeyFNPHNLNTJNMAEE-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
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.62ALOGPS
logP2.92ChemAxon
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 Count22ChemAxon
Refractivity146.28 m³·mol⁻¹ChemAxon
Polarizability54.7 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0000900000-69f3d757e110ec8c3b98Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-2ea2540d550fb015d5e5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-6ab6988a50a1903532bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000900000-c1f627ea020ee6c41402Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-9000500000-4ac5c177695cbcfccf15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-e9262cbaff8cb4ad0ba6Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
SerumDetected and Quantified5.65 +/- 3.92 uMNot AvailableOvine
    • Candidate serum m...
 details
DrugBank IDNot Available
HMDB IDHMDB0000848
FooDB IDFDB022278
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID1585824
BioCyc IDNot Available
METLIN ID5811
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID84644
PubChem Compound ID52922056
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available