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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:22 UTC
HMDB IDHMDB00791
Secondary Accession Numbers
  • HMDB00834
Metabolite Identification
Common NameL-Octanoylcarnitine
DescriptionL-Octanoylcarnitine is the physiologically active form of octanoylcarnitine. (PMID 11274033 ). Octanoylcarnitine is detected in medium-chain acyl-CoA dehydrogenase (MCAD) deficiency. MCAD is characterized by intolerance to prolonged fasting, recurrent episodes of hypoglycemic coma with medium-chain dicarboxylic aciduria, impaired ketogenesis, and low plasma and tissue carnitine levels. (OMIM 201450 ).
Structure
Thumb
Synonyms
ValueSource
L-Octanoyl-L-carnitineChEBI
L-OctanoylcarnitineChEBI
O-Octanoyl-(R)-carnitineChEBI
O-Octanoyl-R-carnitineChEBI
(3R)-3-Octanoyloxy-4-(trimethylazaniumyl)butanoic acidGenerator
(-)-OctanoylcarnitineHMDB
L-Carnitine octanoyl esterHMDB
L-O-OctanoylcarnitineHMDB
Octanoic acid ester with L-(3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner saltHMDB
Octanoyl-L-carnitineHMDB
OctanoylcarnitineHMDB
Chemical FormulaC15H29NO4
Average Molecular Weight287.3951
Monoisotopic Molecular Weight287.209658421
IUPAC Name(3R)-3-(octanoyloxy)-4-(trimethylazaniumyl)butanoate
Traditional NameL-octanoylcarnitine
CAS Registry Number25243-95-2
SMILES
CCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C
InChI Identifier
InChI=1S/C15H29NO4/c1-5-6-7-8-9-10-15(19)20-13(11-14(17)18)12-16(2,3)4/h13H,5-12H2,1-4H3/t13-/m1/s1
InChI KeyInChIKey=CXTATJFJDMJMIY-CYBMUJFWSA-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 Descriptors
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
  • Extracellular
  • Membrane
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 Solubility0.00085 mg/mLALOGPS
logP-1.2ALOGPS
logP-1.5ChemAxon
logS-5.6ALOGPS
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 Count12ChemAxon
Refractivity100.27 m3·mol-1ChemAxon
Polarizability33.22 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)splash10-000i-6090000000-f5427438c18b619c6d12View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-0ffd63a09867f6b170e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-558ce1fa555823e95479View in MoNA
1D NMR1H NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty AcidsSMP00480Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.23 +/- 0.08 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.121 +/- 0.009 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.061 (0.006-0.127) uMChildren (1-13 years old)BothNormal details
FecesDetected and Quantified0 - 4.20 ppmChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableInfant (0-1 year old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.05 (0.03-0.09) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.086 +/- 0.006 uMAdult (>18 years old)BothCeliac disease details
BloodDetected and Quantified0.025 (0.014-0.034) uMAdult (>18 years old)BothVery long-chain acyl-CoA dehydrogenase deficiency (vLCAD) details
FecesDetected and Quantified0 - 10.26 ppmChildren (1-13 years old)Not Specified
Treated celiac disease
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative Colitis
details
Associated Disorders and Diseases
Disease References
Very Long Chain Acyl-CoA Dehydrogenase Deficiency
  1. Costa CG, Struys EA, Bootsma A, ten Brink HJ, Dorland L, Tavares de Almeida I, Duran M, Jakobs C: Quantitative analysis of plasma acylcarnitines using gas chromatography chemical ionization mass fragmentography. J Lipid Res. 1997 Jan;38(1):173-82. [9034211 ]
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 IDFDB022246
KNApSAcK IDNot Available
Chemspider ID10128115
KEGG Compound IDC02838
BioCyc IDL-OCTANOYLCARNITINE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00791
Metagene LinkHMDB00791
METLIN IDNot Available
PubChem Compound11953814
PDB ID1XL8
ChEBI ID18102
References
Synthesis ReferenceDuhr, Edward F.; Mauro, J. Matthew; Clennan, Edward L.; Barden, Roland E. The synthesis and biological activity of thiolcarnitine and its thiolesters. Lipids (1983), 18(5), 382-6.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chace DH, DiPerna JC, Adam BW, Hannon WH: Errors caused by the use of D,L-octanoylcarnitine for blood-spot calibrators. Clin Chem. 2001 Apr;47(4):758-60. [11274033 ]

Enzymes

General function:
Involved in acyltransferase activity
Specific function:
Beta-oxidation of fatty acids. The highest activity concerns the C6 to C10 chain length substrate. Converts the end product of pristanic acid beta oxidation, 4,8-dimethylnonanoyl-CoA, to its corresponding carnitine ester.
Gene Name:
CROT
Uniprot ID:
Q9UKG9
Molecular weight:
10213.63
Reactions
Octanoyl-CoA + L-Carnitine → Coenzyme A + L-Octanoylcarnitinedetails