Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2023-02-21 17:14:42 UTC |
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HMDB ID | HMDB0000321 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 2-Hydroxyadipic acid |
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Description | 2-Hydroxyadipic acid is a hydroxy-dicarboxylic acid formed by the reduction of 2-ketoadipic acid. A deficiency of 2-ketoadipic dehydrogenase causes 2-ketoadipic acidemia or 2-oxoadipic acidemia (OMIM: 245130 ), a genetic disorder characterized by accumulation and excretion of 2-hydroxyadipic acid (with 2-ketoadipic and 2-aminoadipic) (OMMBID - The Online Metabolic and Molecular Bases of Inherited Disease, CH.95). When present in sufficiently high levels, 2-hydroxyadipic acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of 2-hydroxyadipic acid are associated with at least three inborn errors of metabolism including 2-oxoadipic acidemia, 2-aminoadipic aciduria, and 2-oxoadipic aciduria. 2-Hydroxyadipic acid is an organic acid. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart abnormalities, kidney abnormalities, liver damage, seizures, coma, and possibly death. These are also the characteristic symptoms of the untreated IEMs mentioned above. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures. |
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Structure | InChI=1S/C6H10O5/c7-4(6(10)11)2-1-3-5(8)9/h4,7H,1-3H2,(H,8,9)(H,10,11) |
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Synonyms | Value | Source |
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2-Hydroxyadipate | ChEBI | 2-Hydroxyhexanedioic acid | ChEBI | 2-Hydroxyhexanedioate | Generator | 2,3,4-Trideoxyhexarate | HMDB | 2,3,4-Trideoxyhexaric acid | HMDB | 2-Hydroxy-adipate | HMDB | 2-Hydroxy-adipic acid | HMDB | 2-Hydroxy-hexanedioate | HMDB | 2-Hydroxy-hexanedioic acid | HMDB | a-Hydroxyadipate | HMDB | a-Hydroxyadipic acid | HMDB | alpha-Hydroxyadipate | HMDB | alpha-Hydroxyadipic acid | HMDB | DL-2-Hydroxyadipate | HMDB | DL-2-Hydroxyadipic acid | HMDB |
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Chemical Formula | C6H10O5 |
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Average Molecular Weight | 162.1406 |
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Monoisotopic Molecular Weight | 162.05282343 |
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IUPAC Name | 2-hydroxyhexanedioic acid |
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Traditional Name | α-hydroxyadipic acid |
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CAS Registry Number | 18294-85-4 |
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SMILES | OC(CCCC(O)=O)C(O)=O |
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InChI Identifier | InChI=1S/C6H10O5/c7-4(6(10)11)2-1-3-5(8)9/h4,7H,1-3H2,(H,8,9)(H,10,11) |
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InChI Key | OTTXIFWBPRRYOG-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. |
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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 acids and conjugates |
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Direct Parent | Medium-chain fatty acids |
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Alternative Parents | |
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Substituents | - Medium-chain fatty acid
- Hydroxy fatty acid
- Monosaccharide
- Hydroxy acid
- Dicarboxylic acid or derivatives
- Alpha-hydroxy acid
- Secondary alcohol
- Carboxylic acid
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organic oxygen compound
- Organooxygen compound
- Alcohol
- Carbonyl group
- Organic oxide
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | |
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Disposition | |
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Process | |
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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 | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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2-Hydroxyadipic acid,1TMS,isomer #1 | C[Si](C)(C)OC(CCCC(=O)O)C(=O)O | 1561.0 | Semi standard non polar | 33892256 | 2-Hydroxyadipic acid,1TMS,isomer #2 | C[Si](C)(C)OC(=O)CCCC(O)C(=O)O | 1548.0 | Semi standard non polar | 33892256 | 2-Hydroxyadipic acid,1TMS,isomer #3 | C[Si](C)(C)OC(=O)C(O)CCCC(=O)O | 1531.1 | Semi standard non polar | 33892256 | 2-Hydroxyadipic acid,2TMS,isomer #1 | C[Si](C)(C)OC(=O)CCCC(O[Si](C)(C)C)C(=O)O | 1644.9 | Semi standard non polar | 33892256 | 2-Hydroxyadipic acid,2TMS,isomer #2 | C[Si](C)(C)OC(=O)C(CCCC(=O)O)O[Si](C)(C)C | 1615.5 | Semi standard non polar | 33892256 | 2-Hydroxyadipic acid,2TMS,isomer #3 | C[Si](C)(C)OC(=O)CCCC(O)C(=O)O[Si](C)(C)C | 1588.0 | Semi standard non polar | 33892256 | 2-Hydroxyadipic acid,3TMS,isomer #1 | C[Si](C)(C)OC(=O)CCCC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1676.1 | Semi standard non polar | 33892256 | 2-Hydroxyadipic acid,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(CCCC(=O)O)C(=O)O | 1820.0 | Semi standard non polar | 33892256 | 2-Hydroxyadipic acid,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)CCCC(O)C(=O)O | 1794.5 | Semi standard non polar | 33892256 | 2-Hydroxyadipic acid,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)C(O)CCCC(=O)O | 1798.3 | Semi standard non polar | 33892256 | 2-Hydroxyadipic acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)CCCC(O[Si](C)(C)C(C)(C)C)C(=O)O | 2095.4 | Semi standard non polar | 33892256 | 2-Hydroxyadipic acid,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C(CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 2081.5 | Semi standard non polar | 33892256 | 2-Hydroxyadipic acid,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)CCCC(O)C(=O)O[Si](C)(C)C(C)(C)C | 2048.8 | Semi standard non polar | 33892256 | 2-Hydroxyadipic acid,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)CCCC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2313.5 | Semi standard non polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - 2-Hydroxyadipic acid GC-MS (3 TMS) | splash10-00c0-2920000000-14e371ab410997076c08 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 2-Hydroxyadipic acid GC-MS (Non-derivatized) | splash10-00c0-2920000000-14e371ab410997076c08 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Hydroxyadipic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-00xu-9200000000-a5e63603281ceddefa05 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Hydroxyadipic acid GC-MS (3 TMS) - 70eV, Positive | splash10-01w0-9273000000-da104d83dee59e6410a4 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Hydroxyadipic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Hydroxyadipic acid GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Hydroxyadipic acid GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Hydroxyadipic acid GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Hydroxyadipic acid GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Hydroxyadipic acid GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Hydroxyadipic acid GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Hydroxyadipic acid GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Hydroxyadipic acid GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Hydroxyadipic acid GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Hydroxyadipic acid GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Hydroxyadipic acid GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Hydroxyadipic acid GC-MS (TBDMS_2_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Hydroxyadipic acid GC-MS (TBDMS_3_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Hydroxyadipic acid Quattro_QQQ 10V, Negative-QTOF (Annotated) | splash10-03di-2900000000-00b8bf461ba454c702f9 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Hydroxyadipic acid Quattro_QQQ 25V, Negative-QTOF (Annotated) | splash10-0ab9-9000000000-cbfcbe2f1e74c7fa8544 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Hydroxyadipic acid Quattro_QQQ 40V, Negative-QTOF (Annotated) | splash10-052f-9000000000-1a3f1223d56568a37ca5 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Hydroxyadipic acid 10V, Negative-QTOF | splash10-03di-3900000000-2f9a1134097c3e464cfa | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Hydroxyadipic acid 40V, Negative-QTOF | splash10-0a4i-9000000000-38b55b37770b02b19786 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Hydroxyadipic acid 20V, Negative-QTOF | splash10-0600-9200000000-2e8f145f65b692f6de62 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyadipic acid 10V, Positive-QTOF | splash10-0002-1900000000-c97aa5c57fc34910b084 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyadipic acid 20V, Positive-QTOF | splash10-00kb-9800000000-8b422e7bd31b7715f936 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyadipic acid 40V, Positive-QTOF | splash10-0596-9000000000-145898d967788e6a4370 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyadipic acid 10V, Negative-QTOF | splash10-03dl-0900000000-b8d680487ea735b08660 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyadipic acid 20V, Negative-QTOF | splash10-014m-5900000000-2748f3664e3329b9721b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyadipic acid 40V, Negative-QTOF | splash10-0aba-9000000000-7bd0454dd4e607bf327d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyadipic acid 10V, Positive-QTOF | splash10-002b-7900000000-ffa4a95821301025a0c9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyadipic acid 20V, Positive-QTOF | splash10-05fs-9200000000-91faff169b9ab7ca25fb | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyadipic acid 40V, Positive-QTOF | splash10-0a4l-9000000000-f90638e9886a94d83928 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyadipic acid 10V, Negative-QTOF | splash10-0007-5900000000-6ce0e78d81edfe6486c2 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyadipic acid 20V, Negative-QTOF | splash10-00kb-9500000000-e93f435014ff8c6374e9 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyadipic acid 40V, Negative-QTOF | splash10-0007-9000000000-af7c0163f8f183203d48 | 2021-09-23 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | 2012-12-04 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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Disease References | Colorectal cancer |
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- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
| 2-Ketoadipic acidemia |
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- Peng H, Shinka T, Inoue Y, Mitsubuchi H, Ishimatsu J, Yoshino M, Kuhara T: Asymptomatic alpha-ketoadipic aciduria detected during a pilot study of neonatal urine screening. Acta Paediatr. 1999 Aug;88(8):911-4. [PubMed:10503694 ]
- G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
| Alpha-aminoadipic aciduria |
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- Gray RG, O'Neill EM, Pollitt RJ: Alpha-aminoadipic aciduria: chemical and enzymatic studies. J Inherit Metab Dis. 1980;2(4):89-92. [PubMed:6796766 ]
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General References | - Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
- Sewell AC, Heil M, Podebrad F, Mosandl A: Chiral compounds in metabolism: a look in the molecular mirror. Eur J Pediatr. 1998 Mar;157(3):185-91. [PubMed:9537483 ]
- Inoue Y, Shinka T, Ohse M, Kuhara T: Differential chemical diagnosis of primary hyperoxaluria type II. Highly sensitive analysis of optical isomers of glyceric acid by GC/MS as diastereoisomeric derivatives. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 25;823(1):2-6. Epub 2005 Apr 25. [PubMed:16055048 ]
- Svendsen JS, Whist JE, Sydnes LK: Absolute configuration of 3-hydroxyadipic acid in human urine. J Chromatogr. 1985 Jan 11;337(1):9-19. [PubMed:3980660 ]
- 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 ]
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