Stearoylcarnitine (CHEM034979)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:23:22 UTC
Update Date2016-11-09 01:21:13 UTC
Accession NumberCHEM034979
Identification
Common NameStearoylcarnitine
ClassSmall Molecule
DescriptionAn O-acyl-L-carnitine in which the acyl group is specified as stearoyl (octadecanoyl).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical 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 Mass427.661 g/mol
Monoisotopic Mass427.366 g/mol
CAS Registry Number1976-27-8
IUPAC Name(3R)-3-(octadecanoyloxy)-4-(trimethylazaniumyl)butanoate
Traditional Namestearoylcarnitine
SMILESCCCCCCCCCCCCCCCCCC(=O)OC(CC([O-])=O)C[N+](C)(C)C
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.0e-05 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20538056
2. Zhou, Qingzhong. Synthesis of branched-chain analogs of stearoyl carnitine and tests for their abilities to inhibited protein kinase C. Beijing Daxue Xuebao, Ziran Kexueban (1992), 28(2), 143-9.
3. Kamimori H, Hamashima Y, Konishi M: Determination of carnitine and saturated-acyl group carnitines in human urine by high-performance liquid chromatography with fluorescence detection. Anal Biochem. 1994 May 1;218(2):417-24.
4. Bell FP: Carnitine esters: novel inhibitors of plasma lecithin: cholesterol acyltransferase in experimental animals but not in man (Homo sapiens). Int J Biochem. 1983;15(2):133-6.
5. Minkler PE, Ingalls ST, Hoppel CL: High-performance liquid chromatographic separation of acylcarnitines following derivatization with 4'-bromophenacyl trifluoromethanesulfonate. Anal Biochem. 1990 Feb 15;185(1):29-35.
6. Fingerhut R, Roschinger W, Muntau AC, Dame T, Kreischer J, Arnecke R, Superti-Furga A, Troxler H, Liebl B, Olgemoller B, Roscher AA: Hepatic carnitine palmitoyltransferase I deficiency: acylcarnitine profiles in blood spots are highly specific. Clin Chem. 2001 Oct;47(10):1763-8.
7. Minkler PE, Kerner J, North KN, Hoppel CL: Quantitation of long-chain acylcarnitines by HPLC/fluorescence detection: application to plasma and tissue specimens from patients with carnitine palmitoyltransferase-II deficiency. Clin Chim Acta. 2005 Feb;352(1-2):81-92.
8. Zhang AQ, Mitchell SC, Ayesh R, Smith RL: Determination of trimethylamine and related aliphatic amines in human urine by head-space gas chromatography. J Chromatogr. 1992 Dec 23;584(2):141-5.
9. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
10. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
11. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
12. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
13. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
14. The lipid handbook with CD-ROM