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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-01-13 00:26:15 UTC
HMDB IDHMDB0000791
Secondary Accession Numbers
  • HMDB00791
  • 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 ). L-Octanoylcarnitine is also found to be associated with celiac disease and glutaric aciduria II, which are inborn errors of metabolism.
Structure
Thumb
Synonyms
ValueSource
L-Octanoyl-L-carnitineChEBI
O-Octanoyl-(R)-carnitineChEBI
O-Octanoyl-R-carnitineChEBI
(-)-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
Octanoylcarnitine chloride, (R)-isomerMeSH
Octanoylcarnitine, (R)-isomerMeSH
Octanoylcarnitine chlorideMeSH
Octanoylcarnitine chloride, (+-)-isomerMeSH
Octanoylcarnitine, (+-)-isomerMeSH
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 KeyCXTATJFJDMJMIY-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
  • 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
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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity100.27 m³·mol⁻¹ChemAxon
Polarizability33.22 ųChemAxon
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 AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty AcidsPw000171Pw000171 greyscalePw000171 simpleNot 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 Quantified0.17-0.50 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified<0.22 uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified0.21(0.06) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.18 +/- 0.07 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.17-0.50 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 Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Infant (0-1 year old)Both
Normal
details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified60.81 +/- 2.32 umol/mmol creatinineAdolescent (13-18 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 Quantified0.37 uMAdolescent (13-18 years old)Male
Glutaric aciduria II
details
BloodDetected and Quantified0.59 uMAdolescent (13-18 years old)MaleGlutaric aciduria II details
BloodDetected and Quantified0.0943 (0.04369) uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect details
BloodDetected and Quantified0.26(0.08) uMAdult (>18 years old)BothHeart failure with preserved ejection fraction details
BloodDetected and Quantified0.1304 (0.0496) uMAdult (>18 years old)FemalePregnancy details
BloodDetected and Quantified0.025 (0.014-0.034) uMAdult (>18 years old)BothVery long-chain acyl-CoA dehydrogenase deficiency (vLCAD) details
BloodDetected and Quantified0.140 +/- 0.033 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
BloodDetected and Quantified0.160 +/- 0.069 uMChildren (1-13 years old)Both
Obesity
    • Metabolomics reve...
details
FecesDetected and Quantified0 - 10.26 ppmChildren (1-13 years old)Not Specified
Treated celiac disease
details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedUnclassified IBD details
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative Colitis
details
UrineDetected and Quantified69.63 +/- 2.32 umol/mmol creatinineAdolescent (13-18 years old)Both
Obese
details
UrineDetected and Quantified14.246-418.887 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedMedium Chain Acyl-CoA Dehydrogenase Deficiency 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 ]
Glutaric aciduria II
  1. Prasad M, Hussain S: Glutaric aciduria type II presenting as myopathy and rhabdomyolysis in a teenager. J Child Neurol. 2015 Jan;30(1):96-9. doi: 10.1177/0883073813516676. Epub 2014 Jan 21. [PubMed:24453145 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022246
KNApSAcK IDNot Available
Chemspider ID10128115
KEGG Compound IDC02838
BioCyc IDL-OCTANOYLCARNITINE
BiGG IDNot Available
Wikipedia LinkNot Available
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. [PubMed: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