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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-27 16:50:26 UTC
HMDB IDHMDB0000848
Secondary Accession Numbers
  • HMDB0062532
  • HMDB00848
  • HMDB62532
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 (PMID: 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, 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
Data?1582752160
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 Weight427.67
Monoisotopic Molecular Weight427.366159062
IUPAC Name(3R)-3-(octadecanoyloxy)-4-(trimethylazaniumyl)butanoate
Traditional Namestearoylcarnitine
CAS Registry Number25597-09-5
SMILES
CCCCCCCCCCCCCCCCCC(=O)O[C@H](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/t23-/m1/s1
InChI KeyFNPHNLNTJNMAEE-HSZRJFAPSA-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
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
Polarizability54.7 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
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
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
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 but not Quantified Adult (>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
UrineDetected and Quantified0.0-0.07 umol/mmol creatinineNewborn (0-30 days old)BothNormal
    • López Hernández Y...
details
UrineDetected and Quantified0.01(0.0-0.1) umol/mmol creatinineNewborn (0-30 days old)FemaleNormal
    • López Hernández Y...
details
UrineDetected and Quantified0.01(0.0-0.02) umol/mmol creatinineNewborn (0-30 days old)MaleNormal
    • López Hernández Y...
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 ]
Pregnancy
  1. Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Obesity
  1. Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022278
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID1585824
Wikipedia LinkNot Available
METLIN ID5811
PubChem Compound52922056
PDB IDNot Available
ChEBI ID84644
Food Biomarker OntologyNot Available
VMH 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. [PubMed:8074302 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  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 ]
  7. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  8. 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. [PubMed:16902246 ]
  9. 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. [PubMed:17374880 ]
  10. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  11. 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. [PubMed:32033212 ]
  12. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.