Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2007-05-23 12:54:59 UTC |
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Update Date | 2021-09-14 15:43:22 UTC |
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HMDB ID | HMDB0006509 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Nervonyl carnitine |
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Description | Nervonyl carnitine is an acylcarnitine. Numerous disorders have been described that lead to disturbances in energy production and in intermediary metabolism in the organism which are characterized by the production and excretion of unusual acylcarnitines. A mutation in the gene coding for carnitine-acylcarnitine translocase or the OCTN2 transporter aetiologically causes a carnitine deficiency that results in poor intestinal absorption of dietary L-carnitine, its impaired reabsorption by the kidney and, consequently, in increased urinary loss of L-carnitine. Determination of the qualitative pattern of acylcarnitines can be of diagnostic and therapeutic importance. The betaine structure of carnitine requires special analytical procedures for recording. The ionic nature of L-carnitine causes a high water solubility which decreases with increasing chain length of the ester group in the acylcarnitines. Therefore, the distribution of L-carnitine and acylcarnitines in various organs is defined by their function and their physico-chemical properties as well. High performance liquid chromatography (HPLC) permits screening for free and total carnitine, as well as complete quantitative acylcarnitine determination, including the long-chain acylcarnitine profile. (PMID: 17508264 , Monatshefte fuer Chemie (2005), 136(8), 1279-1291., Int J Mass Spectrom. 1999;188:39-52.). |
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Structure | CCCCCCCC\C=C/CCCCCCCCCCCCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C InChI=1S/C31H59NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-31(35)36-29(27-30(33)34)28-32(2,3)4/h12-13,29H,5-11,14-28H2,1-4H3/b13-12-/t29-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C31H60NO4 |
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Average Molecular Weight | 510.823 |
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Monoisotopic Molecular Weight | 510.451685836 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 1242471-01-7 |
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SMILES | CCCCCCCC\C=C/CCCCCCCCCCCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C |
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InChI Identifier | InChI=1S/C31H59NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-31(35)36-29(27-30(33)34)28-32(2,3)4/h12-13,29H,5-11,14-28H2,1-4H3/p+1/b13-12-/t29-/m1/s1 |
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InChI Key | QGIHQXKFCAACHN-BKAVPCLVSA-O |
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Chemical Taxonomy |
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Classification | Not classified |
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Ontology |
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Physiological effect | |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | Property | Value | Source |
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Water Solubility | 0.011 g/L | ALOGPS |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Nervonyl carnitine,1TMS,isomer #1 | CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C)C[N+](C)(C)C | 3577.6 | Semi standard non polar | 33892256 | Nervonyl carnitine,1TMS,isomer #1 | CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C)C[N+](C)(C)C | 3465.9 | Standard non polar | 33892256 | Nervonyl carnitine,1TMS,isomer #1 | CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C)C[N+](C)(C)C | 3843.2 | Standard polar | 33892256 | Nervonyl carnitine,1TBDMS,isomer #1 | CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C[N+](C)(C)C | 3815.8 | Semi standard non polar | 33892256 | Nervonyl carnitine,1TBDMS,isomer #1 | CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C[N+](C)(C)C | 3629.8 | Standard non polar | 33892256 | Nervonyl carnitine,1TBDMS,isomer #1 | CCCCCCCC/C=C\CCCCCCCCCCCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C[N+](C)(C)C | 3865.2 | Standard polar | 33892256 |
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Disease References | Metastatic melanoma |
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- Frankel AE, Coughlin LA, Kim J, Froehlich TW, Xie Y, Frenkel EP, Koh AY: Metagenomic Shotgun Sequencing and Unbiased Metabolomic Profiling Identify Specific Human Gut Microbiota and Metabolites Associated with Immune Checkpoint Therapy Efficacy in Melanoma Patients. Neoplasia. 2017 Oct;19(10):848-855. doi: 10.1016/j.neo.2017.08.004. Epub 2017 Sep 15. [PubMed:28923537 ]
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