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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-11-24 22:14:26 UTC
NP-MRD IDNP0000302
Secondary Accession NumbersNone
Natural Product 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
L-OctanoylcarnitineChEBI
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
Octanoylcarnitine chloride, (R)-isomerHMDB
Octanoylcarnitine, (R)-isomerHMDB
Octanoylcarnitine chlorideHMDB
Octanoylcarnitine chloride, (+-)-isomerHMDB
Octanoylcarnitine, (+-)-isomerHMDB
C8-CarnitineHMDB
OctanoylcarnitineHMDB
Chemical FormulaC15H29NO4
Average Mass287.3951 Da
Monoisotopic Mass287.20966 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
  • Animalia
  • Species Where Detected
    Species NameSourceReference
    Homo sapiens (Urine)KNApSAcK Database
    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
    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
    Polarizability33.28 ųChemAxon
    Number of Rings0ChemAxon
    BioavailabilityYesChemAxon
    Rule of FiveYesChemAxon
    Ghose FilterNoChemAxon
    Veber's RuleNoChemAxon
    MDDR-like RuleNoChemAxon
    HMDB IDHMDB0000791
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB022246
    KNApSAcK IDC00052367
    Chemspider ID10128115
    KEGG Compound IDC02838
    BioCyc IDL-OCTANOYLCARNITINE
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound11953814
    PDB IDNot Available
    ChEBI ID18102
    Good Scents IDNot Available
    References
    General References
    1. Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]
    2. 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 ]
    3. 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 ]
    4. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]
    5. Xiao JF, Varghese RS, Zhou B, Nezami Ranjbar MR, Zhao Y, Tsai TH, Di Poto C, Wang J, Goerlitz D, Luo Y, Cheema AK, Sarhan N, Soliman H, Tadesse MG, Ziada DH, Ressom HW: LC-MS based serum metabolomics for identification of hepatocellular carcinoma biomarkers in Egyptian cohort. J Proteome Res. 2012 Dec 7;11(12):5914-23. doi: 10.1021/pr300673x. Epub 2012 Nov 1. [PubMed:23078175 ]