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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-04-16 17:00:07 UTC
HMDB IDHMDB0000848
Secondary Accession Numbers
  • HMDB00848
Metabolite Identification
Common NameStearoylcarnitine
DescriptionStearoylcarnitine, also known as acylcarnitine C18:0, is a fatty ester lipid molecule. It is found in significantly greater amounts of patients with carnitine palmitoyltransferase (CPT) II deficiency when compared to controls (PubMed 15653102). Stearoylcarnitine is also found to be associated with Celiac disease, another inborn error of metabolism. 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 ). Stearoylcarnitine is considered to be practically insoluble (in water) and acidic.
Structure
Thumb
Synonyms
ValueSource
(-)-StearoylcarnitineChEBI
(R)-OctadecanoylcarnitineChEBI
(R)-StearoylcarnitineChEBI
Acylcarnitine C18:0ChEBI
L-StearoylcarnitineChEBI
O-Octadecanoyl-(R)-carnitineChEBI
O-Stearoyl-L-carnitineChEBI
OctadecanoylcarnitineChEBI
StearoylcarnitineChEBI
Chemical FormulaC25H49NO4
Average Molecular Weight427.67
Monoisotopic Molecular Weight427.366159062
IUPAC Name(3R)-3-(octadecanoyloxy)-4-(trimethylazaniumyl)butanoate
Traditional Namestearoylcarnitine
CAS Registry Number1976-27-8
SMILES
[H][C@@](CC([O-])=O)(C[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC
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/t23-/m1/s1
InChI KeyFNPHNLNTJNMAEE-HSZRJFAPSA-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
  • 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

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility1.0e-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
Polarizability54.53 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biospecimen Locations
  • Blood
  • Feces
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty AcidsThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.04 +/- 0.01 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.080 +/- 0.004 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.020-0.070 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.04 +/- 0.01 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.020-0.070 uMAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0.64 +/- 0.56 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0.24 +/- 0.13 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.076 +/- 0.004 uMAdult (>18 years old)BothCeliac disease details
BloodDetected and Quantified0.0258 (0.018) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified0.0371 (0.0085) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified0.036 +/- 0.012 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified0.040 +/- 0.013 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
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. [PubMed:16425363 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52922056
PDB IDNot Available
ChEBI ID84644
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:1484098 ]