Record Information |
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Version | 1.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2020-11-24 22:14:26 UTC |
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NP-MRD ID | NP0000302 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | L-Octanoylcarnitine |
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Description | L-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. |
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Structure | CCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C 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 |
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Synonyms | Value | Source |
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L-Octanoyl-L-carnitine | ChEBI | L-Octanoylcarnitine | ChEBI | O-Octanoyl-(R)-carnitine | ChEBI | O-Octanoyl-R-carnitine | ChEBI | (-)-Octanoylcarnitine | HMDB | L-Carnitine octanoyl ester | HMDB | L-O-Octanoylcarnitine | HMDB | Octanoic acid ester with L-(3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner salt | HMDB | Octanoyl-L-carnitine | HMDB | Octanoylcarnitine chloride, (R)-isomer | HMDB | Octanoylcarnitine, (R)-isomer | HMDB | Octanoylcarnitine chloride | HMDB | Octanoylcarnitine chloride, (+-)-isomer | HMDB | Octanoylcarnitine, (+-)-isomer | HMDB | C8-Carnitine | HMDB | Octanoylcarnitine | HMDB |
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Chemical Formula | C15H29NO4 |
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Average Mass | 287.3951 Da |
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Monoisotopic Mass | 287.20966 Da |
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IUPAC Name | (3R)-3-(octanoyloxy)-4-(trimethylazaniumyl)butanoate |
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Traditional Name | L-octanoylcarnitine |
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CAS Registry Number | 25243-95-2 |
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SMILES | CCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C |
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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 |
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InChI Key | CXTATJFJDMJMIY-CYBMUJFWSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Species Where Detected | |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acid esters |
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Direct Parent | Acyl carnitines |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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External Links |
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HMDB ID | HMDB0000791 |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB022246 |
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KNApSAcK ID | C00052367 |
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Chemspider ID | 10128115 |
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KEGG Compound ID | C02838 |
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BioCyc ID | L-OCTANOYLCARNITINE |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 11953814 |
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PDB ID | Not Available |
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ChEBI ID | 18102 |
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Good Scents ID | Not Available |
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References |
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General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
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