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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:25 UTC
HMDB IDHMDB00848
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
Synonyms
ValueSource
3-(Octadecanoyloxy)-4-(trimethylammonio)butanoateChEBI
Acylcarnitine C18:0ChEBI
O-OctadecanoylcarnitineChEBI
OctadecanoylcarnitineChEBI
StearoylcarnitineChEBI
3-(Octadecanoyloxy)-4-(trimethylammonio)butanoic acidGenerator
3-Octadecanoyloxy-4-(trimethylazaniumyl)butanoic acidGenerator
(-)-StearoylcarnitineHMDB
(R)-3-Carboxy-N,N,N-trimethyl-2-[(1-oxooctadecyl)oxy]-1-propanaminium inner saltHMDB
(R)-StearoylcarnitineHMDB
L-(3-Carboxy-2-hydroxypropyl)trimethyl-ammonium stearate hydroxide inner saltHMDB
L-Stearic acid ester with (3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner saltHMDB
L-StearoylcarnitineHMDB
Octadecanoyl-L-carnitineHMDB
Stearoyl-L-carnitineHMDB
Chemical FormulaC25H49NO4
Average Molecular Weight427.6609
Monoisotopic Molecular Weight427.366159061
IUPAC Name3-(octadecanoyloxy)-4-(trimethylazaniumyl)butanoate
Traditional Name(-)-stearoylcarnitine
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 KeyInChIKey=FNPHNLNTJNMAEE-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Carnitine
  • Acyl choline
  • Choline
  • Dicarboxylic acid or derivatives
  • Quaternary ammonium salt
  • Carboxylic acid salt
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic zwitterion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Lipid catabolism, Fatty acid transport, Energy production
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.01e-05 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count22ChemAxon
Refractivity146.28 m3·mol-1ChemAxon
Polarizability54.8 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0000900000-69f3d757e110ec8c3b98View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-2ea2540d550fb015d5e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-6ab6988a50a1903532bbView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid Locations
  • Blood
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty AcidsSMP00482Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.04 +/- 0.01 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.080 +/- 0.004 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.076 +/- 0.004 uMAdult (>18 years old)BothCeliac disease details
Associated Disorders and Diseases
Disease References
Celiac disease
  1. Bene J, Komlosi K, Gasztonyi B, Juhasz M, Tulassay Z, Melegh B: Plasma carnitine ester profile in adult celiac disease patients maintained on long-term gluten free diet. World J Gastroenterol. 2005 Nov 14;11(42):6671-5. [16425363 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022278
KNApSAcK IDNot Available
Chemspider ID4932275
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID1585824
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00848
Metagene LinkHMDB00848
METLIN ID5811
PubChem Compound6426855
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceZhou, 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.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [8074302 ]
  2. 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. [2344045 ]
  3. 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. [15653102 ]
  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. [6822312 ]
  5. 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. [11568084 ]
  6. 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. [1484098 ]